dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-61dd76cabf5f48cb8028fe718c7f9d72 | CCOC(=O)c1cc2cccc(Br)c2o1.c1ccc(CCN2CCNCC2)nc1>>CCOC(=O)c1cc2cccc(N3CCN(CCc4ccccn4)CC3)c2o1 | CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br.C1CN(CCN1)CCC2=CC=CC=N2>>CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4 | Br[c:12]1[cH:11][cH:10][cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:28][c:27]21.[NH:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][N:16]([CH2:17][... | CCOC(=O)c1cc2cccc(Br)c2o1.c1ccc(CCN2CCNCC2)nc1 | CCOC(=O)c1cc2cccc(N3CCN(CCc4ccccn4)CC3)c2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CCN2CCN(c3cccc4ccoc34)CC2)nc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7]-[C:8](-[#8:9])=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]:[#8;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1):[c:2]:[c:3] | 39.97 | [{"value": 39.97, "product": "CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | 12/01 2009 15:21:58 +0100 To ethyl 7-bromobenzofuran-2-carboxylate (0.900 g, 3.34 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (0.672 g, 3.51 mmol) in dry degassed dioxane (13 mL) were added Cesium carbonate (1.417 g, 4.35 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.159 g, 0.33 mmol) and Tris(dibe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | c1ccc2occc2c1.C1C[NH]CC[NH]1 | c1ccc2occc2c1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CCOC(=O)c1cc2cccc(Br)c2o1.c1ccc(CCN2CCNCC2)nc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2cccc(N3CCN(CCc4ccccn4)CC3)c2o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3e4ae9ef9d2f47b2b03f41aafafa9bc4 | CCOC(=O)c1cc2cccc(Br)c2o1.c1ccc(CCN2CCNCC2)nc1>>CCOC(=O)c1cc2cccc(N3CCN(CCc4ccccn4)CC3)c2o1 | CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br.C1CN(CCN1)CCC2=CC=CC=N2>>CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4 | Br[c:12]1[cH:11][cH:10][cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:28][c:27]21.[NH:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][N:16]([CH2:17][... | CCOC(=O)c1cc2cccc(Br)c2o1.c1ccc(CCN2CCNCC2)nc1 | CCOC(=O)c1cc2cccc(N3CCN(CCc4ccccn4)CC3)c2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CCN2CCN(c3cccc4ccoc34)CC2)nc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7]-[C:8](-[#8:9])=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]:[#8;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1):[c:2]:[c:3] | 69.5 | [{"value": 69.5, "product": "CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | 17/02 2009 12:47:13 +0100 To ethyl 7-bromobenzofuran-2-carboxylate (1.50 g, 5.57 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (1.120 g, 5.85 mmol) in dry degassed dioxane (20 mL) were added Cesium carbonate (2.361 g, 7.25 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.266 g, 0.56 mmol) and Tris(diben... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | c1ccc2occc2c1.C1C[NH]CC[NH]1 | c1ccc2occc2c1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CCOC(=O)c1cc2cccc(Br)c2o1.c1ccc(CCN2CCNCC2)nc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2cccc(N3CCN(CCc4ccccn4)CC3)c2o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8fcffc24262340ad8745959198669390 | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccc(OCc2ccccc2)cn1>>CC(C)(C)OC(=O)N1CCN(c2ccc(OCc3ccccc3)cn2)CC1 | C1=CC=C(C=C1)COC2=CN=C(C=C2)Cl.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=C(C=C2)OCC3=CC=CC=C3 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:26][CH2:27]1.Cl[c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][n:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][c:1... | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccc(OCc2ccccc2)cn1 | CC(C)(C)OC(=O)N1CCN(c2ccc(OCc3ccccc3)cn2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(COc2ccc(N3CCNCC3)nc2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[#7;a:2]:[c:3] | 68.75 | [{"value": 68.75, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=C(C=C2)OCC3=CC=CC=C3", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | BIS(DIBENZYLIDENEACETONE)PALLADIUM (0.055 g, 0.10 mmol) was added to tert- butyl piperazine-1-carboxylate (1.952 g, 10.48 mmol), 5-(benzyloxy)-2-chloropyridine (2.093 g, 9.53 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.059 g, 0.10 mmol) and sodium 2-methylpropan-2-olate (1.282 g, 13.34 mmol) in toluene (30 mL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccc(OCc2ccccc2)cn1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2ccc(OCc3ccccc3)cn2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-08d5030b9aa741ee93b18633e22acea8 | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | C1=CC(=CC(=C1)OC(F)(F)F)C2=CN=C3N2N=C(C=C3)Cl.Cl.CN1CCC(CC1)CN>>CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2 | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH2:7])[CH2:28][CH2:29]1.Cl[c:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25]3)[n:26]2[n:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH:7][c:8]2[cH:9][cH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][... | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1 | CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 5eed801a0789ef0cf61beb455d5838de5141d4142ef2b34b7746111b27c744b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc3ccc(NCC4CCNCC4)nn23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1 | 55.56 | [{"value": 55.56, "product": "CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A 100 mL round bottom flask was charged with a magnetic stir bar, toluene (17.45 mL), 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine hydrochloride (550 mg, 1.57 mmol) (EN02141-06), Pd2dba3 (144 mg, 0.16 mmol), 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (185 mg, 0.47 mmol),sodium tert-butox... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnn2ccnc2c1 | c1cnn2ccnc2c1 | C1CC[NH]CC1.c1cnn2ccnc2c1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b3b59923db4e4673a6bcde3d5a9c7727 | C1COCCN1.CCOC(=O)c1cnc2cc(OCCOC)c(Br)cc2c1Nc1ccc(C)cc1F>>CCOC(=O)c1cnc2cc(OCCOC)c(N3CCOCC3)cc2c1Nc1ccc(C)cc1F | CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OCCOC)Br)NC3=C(C=C(C=C3)C)F.C1COCCN1>>CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OCCOC)N3CCOCC3)NC4=C(C=C(C=C4)C)F | [NH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1.Br[c:17]1[c:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])[cH:10][c:9]2[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:26]([NH:27][c:28]3[cH:29][cH:30][c:31]([CH3:32])[cH:33][c:34]3[F:35])[c:25]2[cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][c:11... | C1COCCN1.CCOC(=O)c1cnc2cc(OCCOC)c(Br)cc2c1Nc1ccc(C)cc1F | CCOC(=O)c1cnc2cc(OCCOC)c(N3CCOCC3)cc2c1Nc1ccc(C)cc1F | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7aa932588efc8aa136efe0e43f3ce3bc189e51460b145a5586838f54c5c09e43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ccnc3ccc(N4CCOCC4)cc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1-[#8:8].[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7;a:5]:[c:4]1:[c:6]:[c:7](-[#8:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-2):[c:2]:[c:3]:1 | 74.65 | [{"value": 74.65, "product": "CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OCCOC)N3CCOCC3)NC4=C(C=C(C=C4)C)F", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Reaction reference EN00057-06, EN02095-49, 67, 68, 74, 78, 90 In a 50 mL round-bottomed flask was ethyl 6-bromo-4-(2-fluoro-4-methylphenylamino)-7-(2-methoxyethoxy)quinoline-3-carboxylate (4.6911 g, 9.83 mmol), Morpholine (0.857 mL, 9.83 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.720 g, 0.79 mmol), and rac-2,2... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1COCC[NH]1 | c1ccc2ncccc2c1.C1COCC[NH]1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 80 | null | C1COCCN1.CCOC(=O)c1cnc2cc(OCCOC)c(Br)cc2c1Nc1ccc(C)cc1F>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8459652e6963448495d966b232514570 | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | C1=CC=C(C=C1)COC2=CC=C(C=C2)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][NH:14]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][N:14]1[c:15]1... | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | CC(C)(C)[O-].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 35.73 | [{"value": 35.73, "product": "C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | A mixture of 1-(benzyloxy)-4-bromobenzene (158 mg, 0.60 mmol), (R)-tert-butyl 3-methylpiperazine-1-carboxylate (60.1 mg, 0.3 mmol), bis(tri-t- butylphosphine)palladium(0) (15.33 mg, 0.03 mmol) and potassium tert-butoxide (37.0 mg, 0.33 mmol) in THF (2 mL) was flushed with nitrogen and sealed into a microwave tube. The ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1 | 150 | null | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-aba439bdbf614f12a2c2928a8b3049c5 | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | C1=CC=C(C=C1)COC2=CC=C(C=C2)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][NH:14]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][N:14]1[c:15]1... | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.060 g, 0.3 mmol), 1-(benzyloxy)-4-bromobenzene (0.095 g, 0.36 mmol), palladium(II) acetate (6.74 mg, 0.03 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.015 g, 0.02 mmol) and sodium t-butoxide (0.043 g, 0.45 mmol) in toluene (2 mL) was flushed with ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 150 | null | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-53993d3e76914a9480a25e3f9305c2e9 | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | C1=CC=C(C=C1)COC2=CC=C(C=C2)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][NH:14]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][N:14]1[c:15]1... | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | CC(C)(C)[O-].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 31.55 | [{"value": 31.55, "product": "C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 75 | CELSIUS | null | null | A mixture of 1-(benzyloxy)-4-bromobenzene (789 mg, 3.00 mmol), (R)-tert-butyl 3-methylpiperazine-1-carboxylate (300 mg, 1.5 mmol), bis(tri-t- butylphosphine)palladium(0) (77 mg, 0.15 mmol) and potassium tert-butoxide (185 mg, 1.65 mmol) in THF (10 mL) was flushed with nitrogen and heated to 75 °C overnight. A further 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1 | 75 | null | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8d2093b827454e2d9150258e88282b25 | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | C1=CC=C(C=C1)COC2=CC=C(C=C2)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][NH:14]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][N:14]1[c:15]1... | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.072 g, 0.36 mmol), 1-(benzyloxy)-4-bromobenzene (0.079 g, 0.3 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.035 g, 0.06 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.027 g, 0.03 mmol) and sodium 2-methylpropan-2-olate (0.101 g, 1... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 150 | null | Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>C[C@@H]1CN(C(=O)OC(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2e557d69002c4320a9c5c7d56e530a90 | C1CCNCC1.N#Cc1ccc(Br)cc1F>>N#Cc1ccc(N2CCCCC2)cc1F | C1=CC(=C(C=C1Br)F)C#N.C1CCNCC1>>C1CCN(CC1)C2=CC(=C(C=C2)C#N)F | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.Br[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:14]([F:15])[cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14]1[F:15] | C1CCNCC1.N#Cc1ccc(Br)cc1F | N#Cc1ccc(N2CCCCC2)cc1F | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 49.37 | [{"value": 49.37, "product": "C1CCN(CC1)C2=CC(=C(C=C2)C#N)F", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | 4-bromo-2-fluorobenzonitrile (119 mg, 0.59 mmol), Piperidine (0.059 mL, 0.59 mmol), Palladium(II) acetate (6.68 mg, 0.03 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (14.18 mg, 0.03 mmol) and sodium tert-butoxide (57.2 mg, 0.59 mmol) were suspended in toluene (4 mL) and tBuOH (0.800 mL) and heated t... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 160 | null | C1CCNCC1.N#Cc1ccc(Br)cc1F>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>N#Cc1ccc(N2CCCCC2)cc1F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cb91af3b3ac34425a6933ab18a143ee0 | C[C@@H](NC(=O)OC(C)(C)C)c1ccc(Br)cc1.Nc1ncc2cc(-c3ccncc3)cc(Cl)c2n1>>C[C@@H](NC(=O)OC(C)(C)C)c1ccc(Nc2ncc3cc(-c4ccncc4)cc(Cl)c3n2)cc1 | C[C@H](C1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C.C1=CN=CC=C1C2=CC3=CN=C(N=C3C(=C2)Cl)N>>C[C@H](C1=CC=C(C=C1)NC2=NC=C3C=C(C=C(C3=N2)Cl)C4=CC=NC=C4)NC(=O)OC(C)(C)C | Br[c:14]1[cH:13][cH:12][c:11]([C@@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[cH:34][cH:33]1.[NH2:15][c:16]1[n:17][cH:18][c:19]2[cH:20][c:21](-[c:22]3[cH:23][cH:24][n:25][cH:26][cH:27]3)[cH:28][c:29]([Cl:30])[c:31]2[n:32]1>>[CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10... | C[C@@H](NC(=O)OC(C)(C)C)c1ccc(Br)cc1.Nc1ncc2cc(-c3ccncc3)cc(Cl)c2n1 | C[C@@H](NC(=O)OC(C)(C)C)c1ccc(Nc2ncc3cc(-c4ccncc4)cc(Cl)c3n2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncc3cc(-c4ccncc4)ccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]):[c:4]:[c:5] | 50.96 | [{"value": 50.96, "product": "C[C@H](C1=CC=C(C=C1)NC2=NC=C3C=C(C=C(C3=N2)Cl)C4=CC=NC=C4)NC(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A 250 mL roundbottom flask was charged with 8-chloro-6-(pyridin-4-yl)quinazolin-2-amine (EN01547-76-1; 3.09 g, 12.04 mmol), (R)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (EN01547-74-1; 4.42 g, 14.72 mmol), Pd2(dba)3 (114.4 mg, 2.1 mol % Pd), XantPhos (155.0 mg, 2.2 mol %), and Cs2CO3 (5.57 g, 17.10 mmol). The flask wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncncc2c1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | C[C@@H](NC(=O)OC(C)(C)C)c1ccc(Br)cc1.Nc1ncc2cc(-c3ccncc3)cc(Cl)c2n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5cced2257316472bbbfef637f32f12c1 | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(-n2cncn2)ccc1N>>COc1c(Nc2ccc(-n3cncn3)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 | CC(C)OC(=O)N1CCC(CC1)OC2=C(C(=NC=N2)Cl)OC.CC1=C(C=CC(=N1)N2C=NC=N2)N>>CC1=C(C=CC(=N1)N2C=NC=N2)NC3=C(C(=NC=N3)OC4CCN(CC4)C(=O)OC(C)C)OC | Cl[c:4]1[c:3]([O:2][CH3:1])[c:21]([O:22][CH:23]2[CH2:24][CH2:25][N:26]([C:27](=[O:28])[O:29][CH:30]([CH3:31])[CH3:32])[CH2:33][CH2:34]2)[n:20][cH:19][n:18]1.[NH2:5][c:6]1[cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][cH:13][n:14]2)[n:15][c:16]1[CH3:17]>>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[cH:7][cH:8][c:9](-[n:10]3[cH:11][n:1... | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(-n2cncn2)ccc1N | COc1c(Nc2ccc(-n3cncn3)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 | CC(C)(C)[O-].[Na+] | CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc(Nc2ccc(-n3cncn3)nc2)cc(OC2CCNCC2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[#8:8].[C;D1;H3:9]-[c:10](:[#7;a:11]:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:13](:[c:15]):[c:10](-[C;D1;H3:9]):[#7;a:11]:[c:12]):[c:7]:1-[#8:8] | 48.49 | [{"value": 48.49, "product": "CC1=C(C=CC(=N1)N2C=NC=N2)NC3=C(C(=NC=N3)OC4CCN(CC4)C(=O)OC(C)C)OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Sodium tert-butoxide (8.28 mL, 67.61 mmol) was added portionwise to a mixture of 2-methyl-6-(1H-1,2,4-triazol-1-yl)pyridin-3-amine (4.94 g, 28.17 mmol) isopropyl 4-(6-chloro-5-methoxypyrimidin-4-yloxy)piperidine-1-carboxylate (9.29 g, 28.17 mmol) and in dioxane (136 mL) at 18°C over a period of 1 minute under nitrogen.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1.c1nc[nH]n1.C1CC[NH]CC1 | HCl | CC(C)(C)[O-].[Na+].CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(-n2cncn2)ccc1N>CC(C)(C)[O-].[Na+].CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1c(Nc2ccc(-n3cncn3)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ea73803169b640e3b40a2b6127b91b44 | COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1N.Clc1ncc(Cl)c(-c2cnc3ccccn23)n1>>COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1 | C1=CC2=NC=C(N2C=C1)C3=NC(=NC=C3Cl)Cl.CC(=O)N1CCN(CC1)C2=C(C=C(C(=C2)OC)N)OC>>CC(=O)N1CCN(CC1)C2=C(C=C(C(=C2)OC)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC=C5)Cl)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10]([CH3:11])=[O:12])[CH2:13][CH2:14]2)[c:15]([O:16][CH3:17])[cH:18][c:19]1[NH2:20].Cl[c:21]1[n:22][cH:23][c:24]([Cl:25])[c:26](-[c:27]2[cH:28][n:29][c:30]3[cH:31][cH:32][cH:33][cH:34][n:35]23)[n:36]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:... | COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1N.Clc1ncc(Cl)c(-c2cnc3ccccn23)n1 | COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccn2c(-c3ccnc(Nc4ccc(N5CCNCC5)cc4)n3)cnc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 0 | [{"value": 0.0, "product": "CC(=O)N1CCN(CC1)C2=C(C=C(C(=C2)OC)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC=C5)Cl)OC", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | _3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (132.5 mg, 0.50 mmol)_ _ _ _1-(4-(4-amino-2,5-dimethoxyphenyl)piperazin-1-yl)ethanone (140 mg, 0.50 mmol)_ ___(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (23.14 mg, 0.04 mmol)_ _ _ _cesium carbonate (244 mg, 0.75 mmol)_ ___diacetoxypalladium (4.49 mg, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.c1ccn2ccnc2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1N.Clc1ncc(Cl)c(-c2cnc3ccccn23)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-89a1182c94f742baabcda9e64ef54d27 | C1CCNC1.COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(Cl)ccn23)n1>>COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(N4CCCC4)ccn23)n1 | CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)Cl)Cl)OC.C1CCNC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)N6CCCC6)Cl)OC | [NH:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1.Cl[c:30]1[cH:29][c:28]2[n:27][cH:26][c:25](-[c:24]3[c:22]([Cl:23])[cH:21][n:20][c:19]([NH:18][c:17]4[c:3]([O:2][CH3:1])[cH:4][c:5]([N:6]5[CH2:7][CH2:8][N:9]([C:10]([CH3:11])=[O:12])[CH2:13][CH2:14]5)[cH:15][cH:16]4)[n:39]3)[n:38]2[cH:37][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([... | C1CCNC1.COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(Cl)ccn23)n1 | COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(N4CCCC4)ccn23)n1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5205c19e2f9094a0e1606221641ce8cfeb9472b156b40d798846b10960bb19fb | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(-c2cnc3cc(N4CCCC4)ccn23)nc(Nc2ccc(N3CCNCC3)cc2)n1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:2:[c:8]:[c:9]:1.[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]2:[c:8]:[c:9]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]3-[C:10]-[C:11]-[C:12]-[C:13]-3):[c:2]:[c:3]:1:2 | 0 | [{"value": 0.0, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)N6CCCC6)Cl)OC", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | _pyrrolidine (0.025 mL, 0.30 mmol)_ _was added to a suspension of_ _1-(4-(4-(5-chloro-4-(7-chloroimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)piperazin-1-yl)ethanone (104 mg, 0.20 mmol)_ _ in __dioxane (3.5 mL)_ _, followed by_ _sodium 2-methylpropan-2-olate (58.5 mg, 0.61 mmol)_ _, the mixture was... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccn2ccnc2c1 | c1ccn2ccnc2c1.C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.c1ccn2ccnc2c1.C1CC[NH]C1 | HCl | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1 | 105 | null | C1CCNC1.COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(Cl)ccn23)n1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1>COc1cc(N2CCN(C(C)=O)CC2)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-63adda83987840e4a77972b9a1ad7b3d | C1CCNC1.COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(Cl)ccn23)n1>>COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(N4CCCC4)ccn23)n1 | CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)Cl)Cl)OC.C1CCNC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)N6CCCC6)Cl)OC | [NH:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1.Cl[c:30]1[cH:29][c:28]2[n:27][cH:26][c:25](-[c:24]3[c:22]([Cl:23])[cH:21][n:20][c:19]([NH:18][c:17]4[c:3]([O:2][CH3:1])[cH:4][c:5]([N:6]5[CH2:7][CH2:8][N:9]([C:10]([CH3:11])=[O:12])[CH2:13][CH2:14]5)[cH:15][cH:16]4)[n:39]3)[n:38]2[cH:37][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([... | C1CCNC1.COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(Cl)ccn23)n1 | COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(N4CCCC4)ccn23)n1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5205c19e2f9094a0e1606221641ce8cfeb9472b156b40d798846b10960bb19fb | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(-c2cnc3cc(N4CCCC4)ccn23)nc(Nc2ccc(N3CCNCC3)cc2)n1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:2:[c:8]:[c:9]:1.[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]2:[c:8]:[c:9]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]3-[C:10]-[C:11]-[C:12]-[C:13]-3):[c:2]:[c:3]:1:2 | 2 | [{"value": 2.0, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)N6CCCC6)Cl)OC", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | _pyrrolidine (0.019 mL, 0.22 mmol)_ _was added to a suspension of_ _1-(4-(4-(5-chloro-4-(7-chloroimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)piperazin-1-yl)ethanone (104 mg, 0.20 mmol)_ _ in __dioxane (3.5 mL)_ _, followed by_ _sodium 2-methylpropan-2-olate (58.5 mg, 0.61 mmol)_ _, the mixture was... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccn2ccnc2c1 | c1ccn2ccnc2c1.C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.c1ccn2ccnc2c1.C1CC[NH]C1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | C1CCNC1.COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(Cl)c(-c2cnc3cc(Cl)ccn23)n1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3c40e6ac0b7c4653beac4f187a4bcda3 | Cc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N>>Cc1nc(S(C)(=O)=O)ccc1Nc1ncnc(OC2CCN(C(=O)OC(C)C)CC2)c1C | CC1=C(N=CN=C1Cl)OC2CCN(CC2)C(=O)OC(C)C.CC1=C(C=CC(=N1)S(=O)(=O)C)N>>CC1=C(N=CN=C1OC2CCN(CC2)C(=O)OC(C)C)NC3=C(N=C(C=C3)S(=O)(=O)C)C | Cl[c:13]1[n:14][cH:15][n:16][c:17]([O:18][CH:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][CH:26]([CH3:27])[CH3:28])[CH2:29][CH2:30]2)[c:31]1[CH3:32].[CH3:1][c:2]1[n:3][c:4]([S:5]([CH3:6])(=[O:7])=[O:8])[cH:9][cH:10][c:11]1[NH2:12]>>[CH3:1][c:2]1[n:3][c:4]([S:5]([CH3:6])(=[O:7])=[O:8])[cH:9][cH:10][c:11]1[NH:12][c:1... | Cc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N | Cc1nc(S(C)(=O)=O)ccc1Nc1ncnc(OC2CCN(C(=O)OC(C)C)CC2)c1C | CC(C)(C)[O-].[Na+] | CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2cc(OC3CCNCC3)ncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[C;D1;H3:8].[C;D1;H3:9]-[c:10](:[#7;a:11]:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:13](:[c:15]):[c:10](-[C;D1;H3:9]):[#7;a:11]:[c:12]):[c:7]:1-[C;D1;H3:8] | 54.09 | [{"value": 54.09, "product": "CC1=C(N=CN=C1OC2CCN(CC2)C(=O)OC(C)C)NC3=C(N=C(C=C3)S(=O)(=O)C)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Sodium tert-butoxide (9.83 mL, 80.31 mmol) was added portionwise to isopropyl 4-(6-chloro-5-methylpyrimidin-4-yloxy)piperidine-1-carboxylate (10.50 g, 33.46 mmol) and 2-methyl-6-(methylsulfonyl)pyridin-3-amine (5.92 g, 31.79 mmol) in dioxane (160 mL) at 18ºC over a period of 1 minute under nitrogen. The reaction was de... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1.C1CC[NH]CC1 | HCl | CC(C)(C)[O-].[Na+].CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | Cc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N>CC(C)(C)[O-].[Na+].CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1nc(S(C)(=O)=O)ccc1Nc1ncnc(OC2CCN(C(=O)OC(C)C)CC2)c1C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d5f70214ac20425bbba3af9e0d825482 | C1COCCN1.Nc1cncc(Br)c1>>Nc1cncc(N2CCOCC2)c1 | C1=C(C=NC=C1Br)N.C1COCCN1>>C1COCCN1C2=CN=CC(=C2)N | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.Br[c:6]1[cH:5][n:4][cH:3][c:2]([NH2:1])[cH:13]1>>[NH2:1][c:2]1[cH:3][n:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13]1 | C1COCCN1.Nc1cncc(Br)c1 | Nc1cncc(N2CCOCC2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]2-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-2):[c:6]:1 | 0 | [{"value": 0.0, "product": "C1COCCN1C2=CN=CC(=C2)N", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | diacetoxypalladium (20.76 mg, 0.09 mmol) was added to 5-bromopyridin-3-amine (160 mg, 0.92 mmol), morpholine (0.403 mL, 4.62 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (64.2 mg, 0.11 mmol) and cesium carbonate (603 mg, 1.85 mmol) in dioxane (5 mL). The resulting solution was stirred at 150 °C in th... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | C1COCCN1.Nc1cncc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Nc1cncc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9c57f3e17c814398b6e1a1b710de4610 | C1COCCN1.Nc1cncc(Br)c1>>Nc1cncc(N2CCOCC2)c1 | C1=C(C=NC=C1Br)N.C1COCCN1>>C1COCCN1C2=CN=CC(=C2)N | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.Br[c:6]1[cH:5][n:4][cH:3][c:2]([NH2:1])[cH:13]1>>[NH2:1][c:2]1[cH:3][n:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13]1 | C1COCCN1.Nc1cncc(Br)c1 | Nc1cncc(N2CCOCC2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]2-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-2):[c:6]:1 | 0 | [{"value": 0.0, "product": "C1COCCN1C2=CN=CC(=C2)N", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | diacetoxypalladium (20.76 mg, 0.09 mmol) was added to 5-bromopyridin-3-amine (160 mg, 0.92 mmol), morpholine (4028 µl, 46.24 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (64.2 mg, 0.11 mmol) and cesium carbonate (603 mg, 1.85 mmol). The resulting suspension was stirred at 150 °C for 30 minutes in a m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | C1COCCN1.Nc1cncc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Nc1cncc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-20af979b60da4f278f5b92ae2abaf8ca | CC(Nc1nc(Cl)nc(N2CCOCC2)c1F)c1ncc(F)cc1F.Cc1cc(N)nn1C(=O)OC(C)(C)C>>Cc1cc(Nc2nc(NC(C)c3ncc(F)cc3F)c(F)c(N3CCOCC3)n2)n[nH]1 | CC(C1=C(C=C(C=N1)F)F)NC2=C(C(=NC(=N2)Cl)N3CCOCC3)F.CC1=CC(=NN1C(=O)OC(C)(C)C)N>>CC1=CC(=NN1)NC2=NC(=C(C(=N2)N3CCOCC3)F)NC(C)C4=C(C=C(C=N4)F)F | Cl[c:6]1[n:7][c:8]([NH:9][CH:10]([CH3:11])[c:12]2[n:13][cH:14][c:15]([F:16])[cH:17][c:18]2[F:19])[c:20]([F:21])[c:22]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[n:29]1.CC(C)(C)OC(=O)[n:31]1[c:2]([CH3:1])[cH:3][c:4]([NH2:5])[n:30]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([NH:9][CH:10]([CH3:11])[c:12]3[n:13... | CC(Nc1nc(Cl)nc(N2CCOCC2)c1F)c1ncc(F)cc1F.Cc1cc(N)nn1C(=O)OC(C)(C)C | Cc1cc(Nc2nc(NC(C)c3ncc(F)cc3F)c(F)c(N3CCOCC3)n2)n[nH]1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | fcb77e532fa93e7a338db3b67367cc04556344a257e21c542dc780a9312be270 | 714b1e79c619852a8cc4d3efd820398d7a36b06618a87a6b24e58724f087eb50 | c1ccc(CNc2cc(N3CCOCC3)nc(Nc3cc[nH]n3)n2)nc1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[NH2;D1;+0:4]):[c:5]:[c:6]:1-[C;D1;H3:7].Cl-[c;H0;D3;+0:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:7]-[c:6]1:[c:5]:[c:3](-[NH;D2;+0:4]-[c;H0;D3;+0:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[#7;a:2]:[nH;D2;+0:1]:1 | 0 | [{"value": 0.0, "product": "CC1=CC(=NN1)NC2=NC(=C(C(=N2)N3CCOCC3)F)NC(C)C4=C(C=C(C=N4)F)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27.9 mg, 0.05 mmol), 2-chloro-N-(1-(3,5-difluoropyridin-2-yl)ethyl)-5-fluoro-6-morpholinopyrimidin-4-amine (200 mg, 0.54 mmol), tert-butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate (127 mg, 0.64 mmol) and cesium carbonate (349 mg, 1.07 mmol) were added to dioxane (8 mL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Ether.Primary amine.Boc | Secondary amine | c1cncnc1.c1cc[nH]n1 | c1cn[nH]c1.c1cncnc1 | c1cn[nH]c1.c1cncnc1.c1ccncc1.C1COCC[NH]1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CC(Nc1nc(Cl)nc(N2CCOCC2)c1F)c1ncc(F)cc1F.Cc1cc(N)nn1C(=O)OC(C)(C)C>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5ee406d12bbe4c6fbfb323cf21dcbb47 | Brc1cccnc1.C1CNCCN1>>c1cncc(N2CCNCC2)c1 | C1=CC(=CN=C1)Br.C1CNCCN1>>C1CN(CCN1)C2=CN=CC=C2 | Br[c:5]1[cH:4][n:3][cH:2][cH:1][cH:12]1.[NH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1>>[cH:1]1[cH:2][n:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12]1 | Brc1cccnc1.C1CNCCN1 | c1cncc(N2CCNCC2)c1 | CC(C)(C)[O-].[Na+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=C(C=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2cfe79e260e5807469ed13cb0f911e98374b23b23e32c97becca8eb2afcb1c66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-[C:11]-[C:12]-1 | 0 | [{"value": 0.0, "product": "C1CN(CCN1)C2=CN=CC=C2", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | In a 100 ml RBF, 3-bromopyridine (1.220 mL, 12.66 mmol) was taken in xylenes (20 mL). To this was added tris(dibenzylideneacetone)dipalladium(0) (0.232 g, 0.25 mmol), tri-t-butylphosphine (10%wt in Hexane) (1.281 g, 0.63 mmol) and sodium tert-butoxide (1.825 g, 18.99 mmol). Then piperazine (6.54 g, 75.95 mmol) was adde... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CNCCN1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HBr | CC(C)(C)[O-].[Na+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=C(C=C1)C | 130 | null | Brc1cccnc1.C1CNCCN1>CC(C)(C)[O-].[Na+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=C(C=C1)C>c1cncc(N2CCNCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-eeacd9f15ab048189aee22e65e39160d | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | C1=CC(=CC(=C1)OC(F)(F)F)C2=CN=C3N2N=C(C=C3)Cl.Cl.CN1CCC(CC1)CN>>CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2 | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH2:7])[CH2:28][CH2:29]1.Cl[c:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25]3)[n:26]2[n:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH:7][c:8]2[cH:9][cH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][... | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1 | CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 5eed801a0789ef0cf61beb455d5838de5141d4142ef2b34b7746111b27c744b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc3ccc(NCC4CCNCC4)nn23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1 | 49.52 | [{"value": 49.52, "product": "CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A 50 mL round bottom flask was charged with a magnetic stir bar, toluene (6.376 mL), 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine hydrochloride (200 mg, 0.57 mmol), (1-methylpiperidin-4-yl)methanamine (110 mg, 0.86 mmol), 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (67.4 mg, 0.17 mmol), P... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnn2ccnc2c1 | c1cnn2ccnc2c1 | C1CC[NH]CC1.c1cnn2ccnc2c1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-dc082fad710a4bd8bc62cdd0ba778e89 | Brc1cccc(OCc2ccccc2)n1.C1COCCN1>>c1ccc(COc2cccc(N3CCOCC3)n2)cc1 | C1=CC=C(C=C1)COC2=NC(=CC=C2)Br.C1COCCN1>>C1COCCN1C2=NC(=CC=C2)OCC3=CC=CC=C3 | Br[c:11]1[cH:10][cH:9][cH:8][c:7]([O:6][CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:20][cH:19]2)[n:18]1.[NH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[n:18]2)[cH:19][cH:20]1 | Brc1cccc(OCc2ccccc2)n1.C1COCCN1 | c1ccc(COc2cccc(N3CCOCC3)n2)cc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(COc2cccc(N3CCOCC3)n2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 86.94 | [{"value": 86.94, "product": "C1COCCN1C2=NC(=CC=C2)OCC3=CC=CC=C3", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Reagents split into 2 microwave tubes:- 2-(benzyloxy)-6-bromopyridine (2.641 g, 10.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.092 g, 0.10 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.093 g, 0.15 mmol) ,morpholine (1.045 g, 12.00 mmol) and sodium t-butoxide (1.345 g, 14.00 mmol) were suspended in to... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1COCCN1 | c1ccncc1.C1COCC[NH]1 | c1ccccc1.c1ccncc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 120 | null | Brc1cccc(OCc2ccccc2)n1.C1COCCN1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>c1ccc(COc2cccc(N3CCOCC3)n2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d9a19803873546349da1be049890a71d | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>>CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl.CN1C(=CC=N1)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C | Cl[c:13]1[cH:12][c:11]([NH:10][c:9]2[cH:8][cH:7][cH:6][c:5]3[c:25]2[C:26](=[O:27])[N:2]([CH3:1])[CH2:3][CH2:4]3)[c:23]([Cl:24])[cH:22][n:21]1.[NH2:14][c:15]1[cH:16][cH:17][n:18][n:19]1[CH3:20]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([NH:14][c:15]4[cH:16][cH:17][n:18][n:19]4... | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N | CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4ccn[nH]4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 47.97 | [{"value": 47.97, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.31 mmol), 1-methyl-1H-pyrazol-5-amine (60.3 mg, 0.62 mmol), sodium 2-methylpropan-2-olate (44.7 mg, 0.47 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (38.7 mg, 0.06 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (28.4 mg, 0.03... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1.c1cc[nH]n1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 150 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Nc4c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7ebbc5e119754d3d92d97de9cf239bc6 | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>>CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl.CN1C(=CC=N1)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C | Cl[c:13]1[cH:12][c:11]([NH:10][c:9]2[cH:8][cH:7][cH:6][c:5]3[c:25]2[C:26](=[O:27])[N:2]([CH3:1])[CH2:3][CH2:4]3)[c:23]([Cl:24])[cH:22][n:21]1.[NH2:14][c:15]1[cH:16][cH:17][n:18][n:19]1[CH3:20]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([NH:14][c:15]4[cH:16][cH:17][n:18][n:19]4... | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N | CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4ccn[nH]4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 43.76 | [{"value": 43.76, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.31 mmol), 1-methyl-1H-pyrazol-5-amine (60.3 mg, 0.62 mmol), sodium 2-methylpropan-2-olate (44.7 mg, 0.47 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (35.9 mg, 0.06 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1.c1cc[nH]n1 | HCl | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 150 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e45b32fa63b1416c9334b4592b5aba03 | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>>CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl.CN1C(=CC=N1)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C | Cl[c:13]1[cH:12][c:11]([NH:10][c:9]2[cH:8][cH:7][cH:6][c:5]3[c:25]2[C:26](=[O:27])[N:2]([CH3:1])[CH2:3][CH2:4]3)[c:23]([Cl:24])[cH:22][n:21]1.[NH2:14][c:15]1[cH:16][cH:17][n:18][n:19]1[CH3:20]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([NH:14][c:15]4[cH:16][cH:17][n:18][n:19]4... | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N | CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4ccn[nH]4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 26.93 | [{"value": 26.93, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.31 mmol), 1-methyl-1H-pyrazol-5-amine (60.3 mg, 0.62 mmol), sodium 2-methylpropan-2-olate (44.7 mg, 0.47 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (38.7 mg, 0.06 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (28.4 mg, 0.03... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1.c1cc[nH]n1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Nc4c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-25de45b860ba4949ad9267cb514bb16a | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>>CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl.CN1C(=CC=N1)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C | Cl[c:13]1[cH:12][c:11]([NH:10][c:9]2[cH:8][cH:7][cH:6][c:5]3[c:25]2[C:26](=[O:27])[N:2]([CH3:1])[CH2:3][CH2:4]3)[c:23]([Cl:24])[cH:22][n:21]1.[NH2:14][c:15]1[cH:16][cH:17][n:18][n:19]1[CH3:20]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([NH:14][c:15]4[cH:16][cH:17][n:18][n:19]4... | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N | CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4ccn[nH]4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 30.3 | [{"value": 30.3, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.31 mmol), 1-methyl-1H-pyrazol-5-amine (60.3 mg, 0.62 mmol), sodium 2-methylpropan-2-olate (44.7 mg, 0.47 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (38.7 mg, 0.06 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (28.4 mg, 0.03... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1.c1cc[nH]n1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Nc4c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-80d00cb26739441d887e2e759be183c4 | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>>CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl.CN1C(=CC=N1)N>>CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C | Cl[c:13]1[cH:12][c:11]([NH:10][c:9]2[cH:8][cH:7][cH:6][c:5]3[c:25]2[C:26](=[O:27])[N:2]([CH3:1])[CH2:3][CH2:4]3)[c:23]([Cl:24])[cH:22][n:21]1.[NH2:14][c:15]1[cH:16][cH:17][n:18][n:19]1[CH3:20]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][c:13]([NH:14][c:15]4[cH:16][cH:17][n:18][n:19]4... | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N | CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4ccn[nH]4)c3)c21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 69.85 | [{"value": 69.85, "product": "CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.31 mmol), 1-methyl-1H-pyrazol-5-amine (60.3 mg, 0.62 mmol), cesium carbonate (121 mg, 0.37 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.7 mg, 0.05 mmol) and diacetoxypalladium (5.57 mg, 0.02 mmol) were suspend... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN1CCc2cccc(Nc3cc(Cl)ncc3Cl)c2C1=O.Cn1nccc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN1CCc2cccc(Nc3cc(Nc4ccnn4C)ncc3Cl)c2C1=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9145f2f3fc8144728bdd2b390e48a7d0 | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>>CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CC(C)(C)OC(=O)NC>>CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6 | [CH3:1][NH:2][C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].O=S(=O)(O[c:10]1[cH:11][cH:12][c:13]2[s:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][n:21]5[c:22](=[O:23])[cH:24][c:25]([N:26]6[CH2:27][CH2:28][O:29][CH2:30][CH2:31]6)[n:32][c:33]45)[cH:34][cH:35][cH:36][c:37]3[c:38]2[cH:39]1)C(F)(F)F>>[CH3:1][N:2]([C:3](=... | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12 | CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | c5e80da0d06f3aeb99dd8217a6e4cab413dca955dd9155f8444623e009bfc7d9 | 538b97a9a96524755fe1a26c80cb7b0d86358c2375f4cbbb7cc1f2a5981bff3a | O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccccc34)cccn12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;... | 79.79 | [{"value": 79.79, "product": "CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | tert-butyl methylcarbamate (467 mg, 3.56 mmol) dissolved in dioxane (5ml) was added in one portion to 6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (1000 mg, 1.78 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (40.8 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthene... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Carbamic ester | Carbamic ester | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | c1ccn2ccccc2n1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-57d5091f100248ff80a0ef888a43c83e | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>>CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CC(C)(C)OC(=O)NC>>CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6 | [CH3:1][NH:2][C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].O=S(=O)(O[c:10]1[cH:11][cH:12][c:13]2[s:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][n:21]5[c:22](=[O:23])[cH:24][c:25]([N:26]6[CH2:27][CH2:28][O:29][CH2:30][CH2:31]6)[n:32][c:33]45)[cH:34][cH:35][cH:36][c:37]3[c:38]2[cH:39]1)C(F)(F)F>>[CH3:1][N:2]([C:3](=... | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12 | CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | c5e80da0d06f3aeb99dd8217a6e4cab413dca955dd9155f8444623e009bfc7d9 | 538b97a9a96524755fe1a26c80cb7b0d86358c2375f4cbbb7cc1f2a5981bff3a | O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccccc34)cccn12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;... | 98.31 | [{"value": 98.31, "product": "CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | tert-butyl methylcarbamate (467 mg, 3.56 mmol) dissolved in dioxane (5ml) was added in one portion to 6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (1000 mg, 1.78 mmol) , TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (40.8 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthen... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Carbamic ester | Carbamic ester | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | c1ccn2ccccc2n1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4cc48057d24f4576bf9eff479bcda6f7 | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>>CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CC(C)(C)OC(=O)NC>>CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6 | [CH3:1][NH:2][C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].O=S(=O)(O[c:10]1[cH:11][cH:12][c:13]2[s:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][n:21]5[c:22](=[O:23])[cH:24][c:25]([N:26]6[CH2:27][CH2:28][O:29][CH2:30][CH2:31]6)[n:32][c:33]45)[cH:34][cH:35][cH:36][c:37]3[c:38]2[cH:39]1)C(F)(F)F>>[CH3:1][N:2]([C:3](=... | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12 | CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | c5e80da0d06f3aeb99dd8217a6e4cab413dca955dd9155f8444623e009bfc7d9 | 538b97a9a96524755fe1a26c80cb7b0d86358c2375f4cbbb7cc1f2a5981bff3a | O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccccc34)cccn12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;... | 89.31 | [{"value": 89.31, "product": "CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | tert-butyl methylcarbamate (3.04 g, 23.15 mmol) dissolved in dioxane (5ml) was added in one portion to 6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (6.50g, 11.58 mmol) , TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.265 g, 0.29 mmol) and (9,9-dimethyl-9H-xanthen... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Carbamic ester | Carbamic ester | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | c1ccn2ccccc2n1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-65b9230d98a54611a7b2ba04f46f98c7 | COc1cccc(OC2CCNCC2)c1.FC(F)(F)c1nnc2ccc(Br)cn12>>COc1cccc(OC2CCN(c3ccc4nnc(C(F)(F)F)n4c3)CC2)c1 | C1=CC2=NN=C(N2C=C1Br)C(F)(F)F.COC1=CC(=CC=C1)OC2CCNCC2.Cl>>COC1=CC(=CC=C1)OC2CCN(CC2)C3=CN4C(=NN=C4C(F)(F)F)C=C3 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:26][CH2:27]2)[cH:28]1.Br[c:13]1[cH:14][cH:15][c:16]2[n:17][n:18][c:19]([C:20]([F:21])([F:22])[F:23])[n:24]2[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][c:16]4[n:17][n:18][c:1... | COc1cccc(OC2CCNCC2)c1.FC(F)(F)c1nnc2ccc(Br)cn12 | COc1cccc(OC2CCN(c3ccc4nnc(C(F)(F)F)n4c3)CC2)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=C(C=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d5036d0b3e919dadca24cb3b597eecb9c7845e65da2670a6c8bcb19b4ef47b35 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OC2CCN(c3ccc4nncn4c3)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#7;a:6]:[c:7]:[#7;a:8]:2:[c:9]:1.[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#7;a:6]:[c:7]:[#7;a:8]:2:[c:9]:1)-[C:13]-[C:14] | 30.51 | [{"value": 30.51, "product": "COC1=CC(=CC=C1)OC2CCN(CC2)C3=CN4C(=NN=C4C(F)(F)F)C=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-bromo-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (100 mg, 0.38 mmol), 4-(3-methoxyphenoxy)piperidine hydrochloride (110 mg, 0.45 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (17.56 mg, 0.03 mmol) and Sodium tert-butoxide (0.161 mL, 1.32 mmol) were suspended in xylenes (5 mL), then de-gassed and purg... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccn2cnnc2c1 | C1CC[NH]CC1.c1ccn2cnnc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccn2cnnc2c1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=C(C=C1)C | 100 | null | COc1cccc(OC2CCNCC2)c1.FC(F)(F)c1nnc2ccc(Br)cn12>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=C(C=C1)C>COc1cccc(OC2CCN(c3ccc4nnc(C(F)(F)F)n4c3)CC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b8b79c3ec9d6403bb2571ea1f0499d2f | Cn1nccc1CCOc1ccc(C2CCNCC2)cc1.FC(F)(F)c1nnc2ccc(Br)cn12>>Cn1nccc1CCOc1ccc(C2CCN(c3ccc4nnc(C(F)(F)F)n4c3)CC2)cc1 | C1=CC2=NN=C(N2C=C1Br)C(F)(F)F.CN1C(=CC=N1)CCOC2=CC=C(C=C2)C3CCNCC3>>CN1C(=CC=N1)CCOC2=CC=C(C=C2)C3CCN(CC3)C4=CN5C(=NN=C5C(F)(F)F)C=C4 | [CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([CH:14]2[CH2:15][CH2:16][NH:17][CH2:31][CH2:32]2)[cH:33][cH:34]1.Br[c:18]1[cH:19][cH:20][c:21]2[n:22][n:23][c:24]([C:25]([F:26])([F:27])[F:28])[n:29]2[cH:30]1>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][... | Cn1nccc1CCOc1ccc(C2CCNCC2)cc1.FC(F)(F)c1nnc2ccc(Br)cn12 | Cn1nccc1CCOc1ccc(C2CCN(c3ccc4nnc(C(F)(F)F)n4c3)CC2)cc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=C(C=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d5036d0b3e919dadca24cb3b597eecb9c7845e65da2670a6c8bcb19b4ef47b35 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(CCOc2ccc(C3CCN(c4ccc5nncn5c4)CC3)cc2)[nH]n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#7;a:6]:[c:7]:[#7;a:8]:2:[c:9]:1.[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#7;a:6]:[c:7]:[#7;a:8]:2:[c:9]:1)-[C:13]-[C:14] | 19.14 | [{"value": 19.14, "product": "CN1C(=CC=N1)CCOC2=CC=C(C=C2)C3CCN(CC3)C4=CN5C(=NN=C5C(F)(F)F)C=C4", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | 6-bromo-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (65 mg, 0.24 mmol), 4-(4-(2-(1-methyl-1H-pyrazol-5-yl)ethoxy)phenyl)piperidine (112 mg, 0.24 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (11.41 mg, 0.02 mmol) and Sodium tert-butoxide (0.060 mL, 0.49 mmol) were suspended in xylenes (5 mL), then de-ga... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccn2cnnc2c1 | C1CC[NH]CC1.c1ccn2cnnc2c1 | c1ccn[nH]1.c1ccccc1.C1CC[NH]CC1.c1ccn2cnnc2c1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=C(C=C1)C | 110 | null | Cn1nccc1CCOc1ccc(C2CCNCC2)cc1.FC(F)(F)c1nnc2ccc(Br)cn12>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=C(C=C1)C>Cn1nccc1CCOc1ccc(C2CCN(c3ccc4nnc(C(F)(F)F)n4c3)CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5086568c313949c09e3b4fd70cc4de5e | Clc1ccc(I)c(Cl)c1.OCC1CCNCC1>>OCC1CCN(c2ccc(Cl)cc2Cl)CC1 | C1=CC(=C(C=C1Cl)Cl)I.C1CNCCC1CO>>C1CN(CCC1CO)C2=C(C=C(C=C2)Cl)Cl | I[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[Cl:14].[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:15][CH2:16]1>>[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[Cl:14])[CH2:15][CH2:16]1 | Clc1ccc(I)c(Cl)c1.OCC1CCNCC1 | OCC1CCN(c2ccc(Cl)cc2Cl)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6])-[C:10]-[C:11] | 21.87 | [{"value": 21.87, "product": "C1CN(CCC1CO)C2=C(C=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 125 | CELSIUS | null | null | **_Procedure:_** To a flask was added 1,3-Dichloro-4-iodobenzene (5.89 mL, 43.41 mmol), piperidin-4-ylmethanol (5 g, 43.41 mmol), cesium carbonate (28.3 g, 86.83 mmol), 18-Crown-6 (1.377 g, 5.21 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.811 g, 1.30 mmol), and toluene (50 mL). The mixture was stirred un... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 125 | null | Clc1ccc(I)c(Cl)c1.OCC1CCNCC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>OCC1CCN(c2ccc(Cl)cc2Cl)CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d81e972e76a34c37b97e862475279203 | Clc1ccc(I)c(Cl)c1.OCC1CCNCC1>>OCC1CCN(c2ccc(Cl)cc2Cl)CC1 | C1=CC(=C(C=C1Cl)Cl)I.C1CNCCC1CO>>C1CN(CCC1CO)C2=C(C=C(C=C2)Cl)Cl | I[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[Cl:14].[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:15][CH2:16]1>>[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[Cl:14])[CH2:15][CH2:16]1 | Clc1ccc(I)c(Cl)c1.OCC1CCNCC1 | OCC1CCN(c2ccc(Cl)cc2Cl)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6])-[C:10]-[C:11] | 25.06 | [{"value": 25.06, "product": "C1CN(CCC1CO)C2=C(C=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 125 | CELSIUS | null | null | **_Procedure:_** To a flask was added 1,3-Dichloro-4-iodobenzene (5.89 mL, 43.41 mmol), piperidin-4-ylmethanol (5 g, 43.41 mmol), cesium carbonate (28.3 g, 86.83 mmol), 18-Crown-6 (1.377 g, 5.21 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.811 g, 1.30 mmol), and toluene (50 mL). The mixture was stirred un... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 125 | null | Clc1ccc(I)c(Cl)c1.OCC1CCNCC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>OCC1CCN(c2ccc(Cl)cc2Cl)CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6eea29be7d4b47c5893b1e243ef41836 | CN(C)CCN.Ic1ccccc1>>CN(C)CCNc1ccccc1 | C1=CC=C(C=C1)I.CN(C)CCN>>CN(C)CCNC1=CC=CC=C1 | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH2:6].I[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CN(C)CCN.Ic1ccccc1 | CN(C)CCNc1ccccc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CN(C)CCNC1=CC=CC=C1", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | In a 50 mL round-bottomed flask (t=g) was unsym-Dimethylethylenediamine (1.080 mL, 9.80 mmol), Iodobenzene (0.549 mL, 4.90 mmol), and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.449 g, 0.49 mmol)Cesium carbonate (2.396 g, 7.35 mmol) andCesium carbonate (2.396 g, 7.35 mmol) were added. in DMF (10 mL) ([VOLUME]) to give... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O | 100 | null | CN(C)CCN.Ic1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O>CN(C)CCNc1ccccc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3870c5bc1f6548e38bd05a0e29b91f59 | CC(C)(C)OC(=O)NC1CNC1.COc1cc(Br)ccn1>>COc1cc(N2CC(NC(=O)OC(C)(C)C)C2)ccn1 | COC1=NC=CC(=C1)Br.CC(C)(C)OC(=O)NC1CNC1>>CC(C)(C)OC(=O)NC1CN(C1)C2=CC(=NC=C2)OC | [NH:6]1[CH2:7][CH:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[n:20][cH:19][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]2)[cH:18][cH:19][n:20]1 | CC(C)(C)OC(=O)NC1CNC1.COc1cc(Br)ccn1 | COc1cc(N2CC(NC(=O)OC(C)(C)C)C2)ccn1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7d96f7a54f47c28d94653c84a0fbf6730dce9aa927efbb2bbc79224893f62be0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCC2)ccn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1.[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:8]-[C:9]-[C:10]-2):[c:7]:1 | 100.28 | [{"value": 100.28, "product": "CC(C)(C)OC(=O)NC1CN(C1)C2=CC(=NC=C2)OC", "details": "", "is_desired": true}] | 70 | CELSIUS | null | null | A mixture of all the reactants in toluene was heated in a sealed vial at 70 °C overnight. According to LC-MS the reaction was completed and the product had been formed. Toluene was removed, water was added and the product was extracted with DCM. The organic phase was dried through phase separator and concentrated. The... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNC1.c1ccncc1 | c1ccncc1.C1C[NH]C1 | c1ccncc1.C1C[NH]C1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 70 | null | CC(C)(C)OC(=O)NC1CNC1.COc1cc(Br)ccn1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1cc(N2CC(NC(=O)OC(C)(C)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f3ebf4dfde174cff92751e3b49ce74da | CC(C)(C)OC(=O)NC1CNC1.COc1cc(Br)ccn1>>COc1cc(N2CC(NC(=O)OC(C)(C)C)C2)ccn1 | COC1=NC=CC(=C1)Br.CC(C)(C)OC(=O)NC1CNC1>>CC(C)(C)OC(=O)NC1CN(C1)C2=CC(=NC=C2)OC | [NH:6]1[CH2:7][CH:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[n:20][cH:19][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]2)[cH:18][cH:19][n:20]1 | CC(C)(C)OC(=O)NC1CNC1.COc1cc(Br)ccn1 | COc1cc(N2CC(NC(=O)OC(C)(C)C)C2)ccn1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7d96f7a54f47c28d94653c84a0fbf6730dce9aa927efbb2bbc79224893f62be0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCC2)ccn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1.[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:8]-[C:9]-[C:10]-2):[c:7]:1 | 99.96 | [{"value": 99.96, "product": "CC(C)(C)OC(=O)NC1CN(C1)C2=CC(=NC=C2)OC", "details": "", "is_desired": true}] | 70 | CELSIUS | null | null | A mixture of all the reactants in toluene was heated in a sealed vial at 70 °C overnight. According to LC-MS the reaction was completed and the product had been formed. Toluene was removed, water was added and the product was extracted with DCM. The organic phase was dried through phase separator and concentrated. | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNC1.c1ccncc1 | c1ccncc1.C1C[NH]C1 | c1ccncc1.C1C[NH]C1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 70 | null | CC(C)(C)OC(=O)NC1CNC1.COc1cc(Br)ccn1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1cc(N2CC(NC(=O)OC(C)(C)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ff15f562a6534424848273f847da5684 | CN1CCc2cccc(N)c2C1=O.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C(F)(F)F)cn1 | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CN1CCC2=C(C1=O)C(=CC=C2)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C(F)(F)F)C | [NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]1[C:19](=[O:20])[N:21]([CH3:22])[CH2:23][CH2:24]2.I[c:11]1[cH:10][c:9]([NH:8][c:7]2[c:2]([CH3:1])[n:3][n:4]([CH3:5])[cH:6]2)[n:31][cH:30][c:25]1[C:26]([F:27])([F:28])[F:29]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH:8][c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15... | CN1CCc2cccc(N)c2C1=O.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C(F)(F)F)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cccc(Nc3ccnc(Nc4cn[nH]c4)c3)c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[... | 33.74 | [{"value": 33.74, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C(F)(F)F)C", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | A suspension of 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (23.06 mg, 0.13 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.57 mg, 0.01 mmol) and cesium carb... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1c[nH]nc1.c1ccncc1.c1ccc2c(c1)CC[NH]C2 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | CN1CCc2cccc(N)c2C1=O.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CC3)c(C(F)(F)F)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-86cf849855f845f68ee2526bc9e21e63 | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=CC=CC=C1N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11].I[c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][n:18]([CH3:19])[n:20][c:21]2[CH3:22])[n:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][n:18... | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 85.04 | [{"value": 85.04, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.606 g, 1.05 mmol), diacetoxypalladium (0.118 g, 0.52 mmol), 2-amino-N-methylbenzamide (2.67 g, 17.80 mmol) and N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (4 g, 10.47 mmol) were dissolved in dioxane (120 mL) and argon was let to... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fc2357d340a54ad6a62277f1372b8047 | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=CC=CC=C1N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11].I[c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][n:18]([CH3:19])[n:20][c:21]2[CH3:22])[n:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][n:18... | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 76.94 | [{"value": 76.94, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (76 mg, 0.13 mmol) and diacetoxypalladium (14.77 mg, 0.07 mmol) were dissolved in dioxane (15 mL) and argon was let to bubble in the mixture for 5 minutes. 2-amino-N- methylbenzamide (336 mg, 2.24 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ec30b6a8454048268e227104fe1b995b | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=CC=CC=C1N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11].I[c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][n:18]([CH3:19])[n:20][c:21]2[CH3:22])[n:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([NH:15][c:16]2[cH:17][n:18... | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 94.49 | [{"value": 94.49, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-amino-N-methylbenzamide (39.3 mg, 0.26 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.57 mg, 0.01 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol) and cesium carbonate (85 mg, 0.26 mmol) were dissolved i... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-240c47d4226747c780fd84f26f44a48f | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=C(C=CC=C1OC)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31].I[c:8]1[cH:9][c:10]([NH:11][c:12]2[cH:13][n:14]([CH3:15])[n:16][c:17]2[CH3:18])[n:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[cH:13][n:14]([CH3:15])[n... | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 75 | [{"value": 75.0, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A suspension of 2-amino-6-methoxy-N-methylbenzamide (9.55 g, 52.99 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (13.5 g, 35.33 mmol), diacetoxypalladium (0.397 g, 1.77 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.044 g, 3.53 mmol) and cesium carbonate (20.72 g... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-10a49d7456a04dcab0790ed1d012aba2 | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=C(C=CC=C1OC)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31].I[c:8]1[cH:9][c:10]([NH:11][c:12]2[cH:13][n:14]([CH3:15])[n:16][c:17]2[CH3:18])[n:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[cH:13][n:14]([CH3:15])[n... | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 58.53 | [{"value": 58.53, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a stirred solution of N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (26 g, 68.04 mmol) and 2-amino-6-methoxy-N-methylbenzamide (18.39 g, 102.06 mmol) in dioxane (300 mL) is added cesium carbonate (39.9 g, 122.47 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (3.94 g, 6.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fdc95cd68ff44156ad0fcc365202187d | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=C(C=CC=C1OC)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31].I[c:8]1[cH:9][c:10]([NH:11][c:12]2[cH:13][n:14]([CH3:15])[n:16][c:17]2[CH3:18])[n:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[cH:13][n:14]([CH3:15])[n... | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 47.5 | [{"value": 47.5, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A suspension of [Reactants], N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol), diacetoxypalladium (4.41 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (22.71 mg, 0.04 mmol) and cesium carbonate (256 mg, 0.79 mmol) in dioxane (2 mL) was degassed wi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-183f397304e242fab1c88325fcefdf27 | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=C(C=CC=C1OC)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31].I[c:8]1[cH:9][c:10]([NH:11][c:12]2[cH:13][n:14]([CH3:15])[n:16][c:17]2[CH3:18])[n:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[cH:13][n:14]([CH3:15])[n... | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 52.51 | [{"value": 52.51, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A suspension of [Reactants], N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (2.63 g, 6.88 mmol), diacetoxypalladium (0.077 g, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.398 g, 0.69 mmol) and cesium carbonate (4.48 g, 13.77 mmol) in dioxane (37 mL) was degassed w... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9599676249db417e97cf26e2b355d448 | CN1CCOc2cccc(N)c2C1=O.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CCO3)c(C(F)(F)F)cn1 | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CN1CCOC2=CC=CC(=C2C1=O)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C4C(=CC=C3)OCCN(C4=O)C)C(F)(F)F)C | [NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]1[C:19](=[O:20])[N:21]([CH3:22])[CH2:23][CH2:24][O:25]2.I[c:11]1[cH:10][c:9]([NH:8][c:7]2[c:2]([CH3:1])[n:3][n:4]([CH3:5])[cH:6]2)[n:32][cH:31][c:26]1[C:27]([F:28])([F:29])[F:30]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[cH:6][c:7]1[NH:8][c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14]... | CN1CCOc2cccc(N)c2C1=O.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CCO3)c(C(F)(F)F)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCOc2cccc(Nc3ccnc(Nc4cn[nH]c4)c3)c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[... | 54.21 | [{"value": 54.21, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C4C(=CC=C3)OCCN(C4=O)C)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A suspension of 6-amino-4-methyl-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (151 mg, 0.79 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol), diacetoxypalladium (4.41 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (22.71 mg, 0.04 mmol) and ce... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1c[nH]nc1.c1ccncc1.c1ccc2c(c1)C[NH]CCO2 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN1CCOc2cccc(N)c2C1=O.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1nn(C)cc1Nc1cc(Nc2cccc3c2C(=O)N(C)CCO3)c(C(F)(F)F)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-22901a6299a241baa726d8f567bd79ae | Clc1ccc(Br)c(Cl)n1.Nc1ccccc1>>Clc1ccc(Nc2ccccc2)c(Cl)n1 | C1=CC(=NC(=C1Br)Cl)Cl.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl | Br[c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:15][c:13]1[Cl:14].[NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([Cl:14])[n:15]1 | Clc1ccc(Br)c(Cl)n1.Nc1ccccc1 | Clc1ccc(Nc2ccccc2)c(Cl)n1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 0 | [{"value": 0.0, "product": "C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | BINAP (4.67 mg, 7.50 µmol) and Pd2dba3 (2.289 mg, 2.50 µmol) were dissolved in dioxane (1ml) and flushed with nitrogen. 3-bromo-2,6-dichloropyridine (0.023 g, 0.1 mmol), aniline (0.018 mL, 0.20 mmol) and sodium tert-butoxide (0.014 g, 0.15 mmol) were weight in another flask and flushed with nitrogen. The ligand- Pd mix... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | Clc1ccc(Br)c(Cl)n1.Nc1ccccc1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Clc1ccc(Nc2ccccc2)c(Cl)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7c9ead47a3324fac997f2b8af6afca02 | CC(C)(C)OC(N)=O.O=C(O)c1cc(Cl)nc(Cl)c1>>CC(C)(C)OC(=O)Nc1cc(C(=O)O)cc(Cl)n1 | C1=C(C=C(N=C1Cl)Cl)C(=O)O.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=NC(=CC(=C1)C(=O)O)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8].Cl[c:9]1[cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15][c:16]([Cl:17])[n:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15][c:16]([Cl:17])[n:18]1 | CC(C)(C)OC(N)=O.O=C(O)c1cc(Cl)nc(Cl)c1 | CC(C)(C)OC(=O)Nc1cc(C(=O)O)cc(Cl)n1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | ed01b145192f9cffb3f3553513f8bbd15ca4f246fc1ccc0dad392a1f0f7069ce | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:13]-[C:14](-[NH2;D1;+0:15])=[O;D1;H0:16]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:13]-[C:14](=[O;D1;H0:16])-[NH;D2;+0:15]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6](=[O... | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)NC1=NC(=CC(=C1)C(=O)O)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Reagents were mixed in a 25 mL round bottom flask and flushed well with nitrogen - heated at 100 °C for 16 h. The mixture looked dark black. Could not detect any starting material or product! It was discarded. | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | CC(C)(C)OC(N)=O.O=C(O)c1cc(Cl)nc(Cl)c1>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC(C)(C)OC(=O)Nc1cc(C(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-17f82e7aaf404cf69c8e741e1af8f96f | Clc1ccnc(Cl)c1.Cn1nccc1N>>Cn1nccc1Nc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CN1C(=CC=N1)N>>CN1C(=CC=N1)NC2=NC=CC(=C2)Cl | Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1 | Clc1ccnc(Cl)c1.Cn1nccc1N | Cn1nccc1Nc1cc(Cl)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccn[nH]2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 23.41 | [{"value": 23.41, "product": "CN1C(=CC=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (124 mg, 0.14 mmol) was added in one portion to 2,4-dichloropyridine (200 mg, 1.35 mmol), 1-methyl-1H-pyrazol-5-amine (158 mg, 1.62 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (156 mg, 0.27 mmol), and cesium carbonate (881 mg, 2.70 mmol) in 1,4-dioxane (20 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccn[nH]1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 105 | null | Clc1ccnc(Cl)c1.Cn1nccc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cn1nccc1Nc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1216a944f8b54fd3a989e124edb2145c | Clc1ccnc(Cl)c1.Cn1nccc1N>>Cn1nccc1Nc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CN1C(=CC=N1)N>>CN1C(=CC=N1)NC2=NC=CC(=C2)Cl | Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1 | Clc1ccnc(Cl)c1.Cn1nccc1N | Cn1nccc1Nc1cc(Cl)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccn[nH]2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 9.93 | [{"value": 9.93, "product": "CN1C(=CC=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 200 | CELSIUS | null | null | 2,4-dichloropyridine (100mg, 0.68 mmol), 1-methyl-1H-pyrazol-5-amine (72.2 mg, 0.74 mmol) and cesium carbonate (330 mg, 1.01 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (46.1 mg, 0.08 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (25.06 mg, 0.03 mmol) were suspended in 1,4-dioxane (5 mL) and ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccn[nH]1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 200 | null | Clc1ccnc(Cl)c1.Cn1nccc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cn1nccc1Nc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-90d260fec9dd4d62a1593e5cdff9b43a | Clc1ccnc(Cl)c1.Cn1nccc1N>>Cn1nccc1Nc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CN1C(=CC=N1)N>>CN1C(=CC=N1)NC2=NC=CC(=C2)Cl | Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1 | Clc1ccnc(Cl)c1.Cn1nccc1N | Cn1nccc1Nc1cc(Cl)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccn[nH]2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 50.36 | [{"value": 50.36, "product": "CN1C(=CC=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (251 mg, 0.27 mmol) was [AP-added] to 2,4-dichloropyridine (1000mg, 6.76 mmol), 1-methyl-1H-pyrazol-5-amine (722 mg, 7.43 mmol), cesium carbonate (3302 mg, 10.14 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (461 mg, 0.80 mmol) in 1,4-dioxane (75 mL) warmed... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccn[nH]1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 105 | null | Clc1ccnc(Cl)c1.Cn1nccc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cn1nccc1Nc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3c8e64b916074a0fa79f8b674402d3e9 | Clc1ccnc(Cl)c1.Cn1nccc1N>>Cn1nccc1Nc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CN1C(=CC=N1)N>>CN1C(=CC=N1)NC2=NC=CC(=C2)Cl | Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1 | Clc1ccnc(Cl)c1.Cn1nccc1N | Cn1nccc1Nc1cc(Cl)ccn1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccn[nH]2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 56.88 | [{"value": 56.88, "product": "CN1C(=CC=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (251 mg, 0.27 mmol) was added in one portion to 2,4-dichloropyridine (1000mg, 6.76 mmol), 1,3-dimethyl-1H-pyrazol-5-amine (826 mg, 7.43 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (461 mg, 0.80 mmol) and sodium tert-butoxide (974 mg, 10.14 mmol) in 1,4-dioxa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccn[nH]1.c1ccncc1 | HCl | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 130 | null | Clc1ccnc(Cl)c1.Cn1nccc1N>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cn1nccc1Nc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-dfcce3a0a05b417eb954f008fad9e74c | Clc1ccnc(Cl)c1.Cn1nccc1N>>Cn1nccc1Nc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CN1C(=CC=N1)N>>CN1C(=CC=N1)NC2=NC=CC(=C2)Cl | Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1 | Clc1ccnc(Cl)c1.Cn1nccc1N | Cn1nccc1Nc1cc(Cl)ccn1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccn[nH]2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 60.25 | [{"value": 60.25, "product": "CN1C(=CC=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (1.238 g, 1.35 mmol) was added in one portion to 2,4-dichloropyridine (10g, 67.57 mmol), 1-methyl-1H-pyrazol-5-amine (7.22 g, 74.33 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.346 g, 4.05 mmol) and sodium tert-butoxide (9.74 g, 101.36 mmol) in 1,4-dioxane... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccn[nH]1.c1ccncc1 | HCl | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 130 | null | Clc1ccnc(Cl)c1.Cn1nccc1N>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cn1nccc1Nc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-67b473c406bc4b47b51604fb52d7c08b | Clc1ccnc(Cl)c1.Cn1nccc1N>>Cn1nccc1Nc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CN1C(=CC=N1)N>>CN1C(=CC=N1)NC2=NC=CC(=C2)Cl | Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1 | Clc1ccnc(Cl)c1.Cn1nccc1N | Cn1nccc1Nc1cc(Cl)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccn[nH]2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 60.54 | [{"value": 60.54, "product": "CN1C(=CC=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (50.1 mg, 0.05 mmol) was added in one portion to 2,4-dichloropyridine (200 mg, 1.35 mmol), 1-methyl-1H-pyrazol-5-amine (144 mg, 1.49 mmol), cesium carbonate (660 mg, 2.03 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (93 mg, 0.16 mmol) in 1,4-dioxane (20 mL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccn[nH]1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 105 | null | Clc1ccnc(Cl)c1.Cn1nccc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cn1nccc1Nc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0394a7894466450da1ab8d7f700166f5 | Clc1ccnc(Cl)c1.Cn1nccc1N>>Cn1nccc1Nc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CN1C(=CC=N1)N>>CN1C(=CC=N1)NC2=NC=CC(=C2)Cl | Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1 | Clc1ccnc(Cl)c1.Cn1nccc1N | Cn1nccc1Nc1cc(Cl)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccn[nH]2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 20.66 | [{"value": 20.66, "product": "CN1C(=CC=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (1.238 g, 1.35 mmol) was added in one portion to 2,4-dichloropyridine (10g, 67.57 mmol), 1-methyl-1H-pyrazol-5-amine (7.22 g, 74.33 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.346 g, 4.05 mmol) and cesium carbonate (33.0 g, 101.36 mmol) in 1,4-dioxane (35... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccn[nH]1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 105 | null | Clc1ccnc(Cl)c1.Cn1nccc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cn1nccc1Nc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-542a3d0745614bcba1a86db54a9cc72d | Clc1ccc(I)c(Cl)n1.Nc1ccccc1>>Clc1ccc(Nc2ccccc2)c(Cl)n1 | C1=CC(=NC(=C1I)Cl)Cl.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl | I[c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:15][c:13]1[Cl:14].[NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([Cl:14])[n:15]1 | Clc1ccc(I)c(Cl)n1.Nc1ccccc1 | Clc1ccc(Nc2ccccc2)c(Cl)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 0 | [{"value": 0.0, "product": "C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | The reaction vessel was charged with nitrogen, BINAP (2.491 mg, 4.00 µmol) and diacetoxypalladium (0.898 mg, 4.00 µmol) were dilutet in toluene (2 ml) and flushed with nitrogen.2,6-dichloro-3-iodopyridine (0.027 g, 0.1 mmol), aniline (10.96 µl, 0.12 mmol) and cesium carbonate (0.163 g, 0.50 mmol) were weight in another... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | Clc1ccc(I)c(Cl)n1.Nc1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Clc1ccc(Nc2ccccc2)c(Cl)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fc9c1fb745cd41db91cc01d3444dd381 | Clc1ccc(I)c(Cl)n1.Nc1ccccc1>>Clc1ccc(Nc2ccccc2)c(Cl)n1 | C1=CC(=NC(=C1I)Cl)Cl.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl | I[c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:15][c:13]1[Cl:14].[NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([Cl:14])[n:15]1 | Clc1ccc(I)c(Cl)n1.Nc1ccccc1 | Clc1ccc(Nc2ccccc2)c(Cl)n1 | C(=O)([O-])[O-].[K+].[K+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 0 | [{"value": 0.0, "product": "C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Biphenyl-2-yldicyclohexylphosphine (2.80 mg, 8.00 µmol) and diacetoxypalladium (0.898 mg, 4.00 µmol) were dilutet in dioxane (1 ml) and flushed with nitrogen. 2,6-dichloro-3-iodopyridine (0.027 g, 0.1 mmol), aniline (10.96 µl, 0.12 mmol) and potassium carbonate (0.276 g, 2.00 mmol) were weight in another flask and flus... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HI | C(=O)([O-])[O-].[K+].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | Clc1ccc(I)c(Cl)n1.Nc1ccccc1>C(=O)([O-])[O-].[K+].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Clc1ccc(Nc2ccccc2)c(Cl)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-91ba9c49c74648a386e9a8da907612ae | Clc1ccc(I)c(Cl)n1.Nc1ccccc1>>Clc1ccc(Nc2ccccc2)c(Cl)n1 | C1=CC(=NC(=C1I)Cl)Cl.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl | I[c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:15][c:13]1[Cl:14].[NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([Cl:14])[n:15]1 | Clc1ccc(I)c(Cl)n1.Nc1ccccc1 | Clc1ccc(Nc2ccccc2)c(Cl)n1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 92.14 | [{"value": 92.14, "product": "C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | The reaction was carried out under nitrogen. Two runs using the same amount of starting material (2,6-dichloro-3-iodopyridine (274 mg, 1 mmol)) and the same conditions were started and carried out as described in the following. BINAP (46.7 mg, 0.08 mmol) and Pd2(dba)3 (22.89 mg, 0.03 mmol) were given into a nitrogen c... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HI | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | Clc1ccc(I)c(Cl)n1.Nc1ccccc1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Clc1ccc(Nc2ccccc2)c(Cl)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2de77de369ef42f8b910f9e83130f454 | CC(C)(C)OC(=O)NC1CCNCC1.COC(=O)c1cccc(Br)c1>>COC(=O)c1cccc(N2CCC(NC(=O)OC(C)(C)C)CC2)c1 | COC(=O)C1=CC(=CC=C1)Br.CC(C)(C)OC(=O)NC1CCNCC1>>CC(C)(C)OC(=O)NC1CCN(CC1)C2=CC=CC(=C2)C(=O)OC | [NH:10]1[CH2:11][CH2:12][CH:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.Br[c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20]... | CC(C)(C)OC(=O)NC1CCNCC1.COC(=O)c1cccc(Br)c1 | COC(=O)c1cccc(N2CCC(NC(=O)OC(C)(C)C)CC2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11](-[C:10]-[C:9])-[C:12]-[C:13]):[c:7]:[c:8] | 13.76 | [{"value": 13.76, "product": "CC(C)(C)OC(=O)NC1CCN(CC1)C2=CC=CC(=C2)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | All chemicals were mixed in a 50 mL round bottom flask. The solids were degassed and placed under nitrogen. Toluene was added and the mixture was stirred at 100°C for 24 h. Cooled and filtered. The filtrate was concentrated under vacuum. Crude product was mainly starting material but some product had been formed. The p... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(=O)NC1CCNCC1.COC(=O)c1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COC(=O)c1cccc(N2CCC(NC(=O)OC(C)(C)C)CC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-81dfebc5c5a442faa29242be372b9cb1 | CC(C)(C)OC(N)=O.Fc1ccnc(Cl)c1>>Nc1cc(F)ccn1 | C1=CN=C(C=C1F)Cl.CC(C)(C)OC(=O)N>>C1=CN=C(C=C1F)N | CC(C)(C)OC(=O)[NH2:1].Cl[c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][n:8]1>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][n:8]1 | CC(C)(C)OC(N)=O.Fc1ccnc(Cl)c1 | Nc1cc(F)ccn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | dea5db4463e7c3cfd5fbe1f28e5d96c30a1e600542b79e5ecb1acf11889c7f56 | 3839d5e915639d5c2dab9e38f5399a1f1f7208a476325eb9f4bbad504346098d | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH2;D1;+0:1].Cl-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6] | 25.34 | [{"value": 25.34, "product": "C1=CN=C(C=C1F)N", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-chloro-4-fluoropyridine (1.5 g, 11.40 mmol), tert-butyl carbamate (1.403 g, 11.97 mmol), CESIUM CARBONATE (7.43 g, 22.81 mmol) ,TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.418 g, 0.46 mmol) and 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (0.528 g, 0.91 mmol) were suspended in 1,4-dioxane (28 ml) ,degased with argon ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester.Ether.Boc | Primary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 90 | null | CC(C)(C)OC(N)=O.Fc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Nc1cc(F)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e759d69f11ae4651a16a93e70cd9c7e3 | COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1N.Fc1cccn2c(-c3nc(Cl)ncc3Cl)cnc12>>COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1Nc1ncc(Cl)c(-c2cnc3c(F)cccn23)n1 | C1=CN2C(=CN=C2C(=C1)F)C3=NC(=NC=C3Cl)Cl.CC(C)(C)OC(=O)CN(C)C1=CC(=C(C=C1)N)OC>>CC(C)(C)OC(=O)CN(C)C1=CC(=C(C=C1)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4F)Cl)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]([CH3:7])[CH2:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17][c:18]1[NH2:19].Cl[c:20]1[n:21][cH:22][c:23]([Cl:24])[c:25](-[c:26]2[cH:27][n:28][c:29]3[c:30]([F:31])[cH:32][cH:33][cH:34][n:35]23)[n:36]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]([CH3:7])[CH2:8][C:9](=[... | COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1N.Fc1cccn2c(-c3nc(Cl)ncc3Cl)cnc12 | COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1Nc1ncc(Cl)c(-c2cnc3c(F)cccn23)n1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3cnc4ccccn34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 43.05 | [{"value": 43.05, "product": "CC(C)(C)OC(=O)CN(C)C1=CC(=C(C=C1)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4F)Cl)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A microwave tube was charged with diacetoxypalladium (11.18 mg, 0.05 mmol), potassium phosphate (529 mg, 2.49 mmol),2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (62.0 mg, 0.10 mmol), 3-(2,5-dichloropyrimidin-4-yl)-8-fluoroimidazo[1,2-a]pyridine (282 mg, 1.00 mmol) purged with nitrogen. Dioxane (4.5 ml) was added followe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccn2ccnc2c1 | HCl | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1N.Fc1cccn2c(-c3nc(Cl)ncc3Cl)cnc12>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1Nc1ncc(Cl)c(-c2cnc3c(F)cccn23)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1a5e116509544433b15ed4392cd63699 | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I>>CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC | C1=C(C(=CN=C1Cl)C(F)(F)F)I.CNC(=O)C1=C(C=CC=C1OC)N>>CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:19][cH:20][cH:21][c:22]1[O:23][CH3:24].I[c:8]1[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][c:22]1[O:23... | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I | CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;... | 63.83 | [{"value": 63.83, "product": "CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (790 mg, 2.57 mmol), 2-amino-6-methoxy-N-methylbenzamide (477 mg, 2.65 mmol), diacetoxypalladium (46.2 mg, 0.21 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (238 mg, 0.41 mmol) and cesium carbonate (1005 mg, 3.08 mmol) were mixed together in dioxane (15 mL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-67600027c34a4dbf95ee52ac1b8cec86 | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I>>CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC | C1=C(C(=CN=C1Cl)C(F)(F)F)I.CNC(=O)C1=C(C=CC=C1OC)N>>CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:19][cH:20][cH:21][c:22]1[O:23][CH3:24].I[c:8]1[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][c:22]1[O:23... | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I | CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;... | 66.13 | [{"value": 66.13, "product": "CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (420 mg, 1.37 mmol), 2-amino-6-methoxy-N-methylbenzamide (246 mg, 1.37 mmol), diacetoxypalladium (24.54 mg, 0.11 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (126 mg, 0.22 mmol) and cesium carbonate (534 mg, 1.64 mmol) were mixed together in dioxane (8 mL)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-322e28476a6147ed99e484e5e4c5349d | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I>>CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC | C1=C(C(=CN=C1Cl)C(F)(F)F)I.CNC(=O)C1=C(C=CC=C1OC)N>>CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:19][cH:20][cH:21][c:22]1[O:23][CH3:24].I[c:8]1[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][c:22]1[O:23... | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I | CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;... | 85.46 | [{"value": 85.46, "product": "CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (7 g, 22.77 mmol), 2-amino-6-methoxy-N-methylbenzamide (4.31 g, 23.91 mmol), diacetoxypalladium (0.409 g, 1.82 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.108 g, 3.64 mmol) and cesium carbonate (8.90 g, 27.32 mmol) were suspended in dioxane (75 ml). Ar... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1c(N)cccc1OC.FC(F)(F)c1cnc(Cl)cc1I>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-34303fd6fd5e47248d4e6485a08472e5 | C1COCCN1.CC(C)(C)OC(=O)Nc1cncc(I)c1>>Nc1cncc(N2CCOCC2)c1 | CC(C)(C)OC(=O)NC1=CC(=CN=C1)I.C1COCCN1>>C1COCCN1C2=CN=CC(=C2)N | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.CC(C)(C)OC(=O)[NH:1][c:2]1[cH:3][n:4][cH:5][c:6](I)[cH:13]1>>[NH2:1][c:2]1[cH:3][n:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13]1 | C1COCCN1.CC(C)(C)OC(=O)Nc1cncc(I)c1 | Nc1cncc(N2CCOCC2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | fa8a4d1111fd9cc8f72ce330d1ca83786f75e7b272f26dc6298f505357aeb4d0 | 77788707fbfb77d4bffd96cd89162b1729d8ed1925842b94a19f07caf9861db0 | c1cncc(N2CCOCC2)c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](-I):[c:5]:[#7;a:6]:[c:7]:1.[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-2):[c:5]:[#7;a:6]:[c:7]:1 | 27.69 | [{"value": 27.69, "product": "C1COCCN1C2=CN=CC(=C2)N", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | morpholine (0.272 mL, 3.12 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.07 mmol), tert-butyl 5-iodopyridin-3-ylcarbamate (200 mg, 0.62 mmol), diacetoxypalladium (7.01 mg, 0.03 mmol) and cesium carbonate (407 mg, 1.25 mmol) were suspended in 1,4-dioxane (4 mL) and sealed into a microwave ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | Primary amine.Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | C1COCCN1.CC(C)(C)OC(=O)Nc1cncc(I)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Nc1cncc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-99e222e4d9a34b6bb8073fb91a88f0f7 | Nc1ccnc(Cl)n1.OCc1ccc(F)c(Br)c1>>OCc1ccc(F)c(Nc2ccnc(Cl)n2)c1 | C1=CC(=C(C=C1CO)Br)F.C1=CN=C(N=C1N)Cl>>C1=CC(=C(C=C1CO)NC2=NC(=NC=C2)Cl)F | [NH2:9][c:10]1[cH:11][cH:12][n:13][c:14]([Cl:15])[n:16]1.Br[c:8]1[c:6]([F:7])[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:17]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([NH:9][c:10]2[cH:11][cH:12][n:13][c:14]([Cl:15])[n:16]2)[cH:17]1 | Nc1ccnc(Cl)n1.OCc1ccc(F)c(Br)c1 | OCc1ccc(F)c(Nc2ccnc(Cl)n2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1=CC(=C(C=C1CO)NC2=NC(=NC=C2)Cl)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | diacetoxypalladium (8.67 mg, 0.04 mmol) was added to 2-chloropyrimidin-4-amine (100 mg, 0.77 mmol), (3-bromo-4-fluorophenyl)methanol (158 mg, 0.77 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (53.6 mg, 0.09 mmol) and cesium carbonate (503 mg, 1.54 mmol) in 1,4-dioxane (4 mL) . The resulting suspensi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | Nc1ccnc(Cl)n1.OCc1ccc(F)c(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>OCc1ccc(F)c(Nc2ccnc(Cl)n2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6a2eab081b6a474896fa34b3a81f3801 | COC(=O)C(C)(C)N.COc1ccc(Br)cc1>>COC(=O)C(C)(C)Nc1ccc(OC)cc1 | COC1=CC=C(C=C1)Br. CC(C)(C(=O)OC)N>>CC(C)(C(=O)OC)NC1=CC=C(C=C1)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[NH2:8].Br[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1 | COC(=O)C(C)(C)N.COc1ccc(Br)cc1 | COC(=O)C(C)(C)Nc1ccc(OC)cc1 | CCC(C)(C)[O-].[Na+] | CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd] | C1=CC=C(C=C1)C(F)(F)F | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH2;D1;+0:13]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CC(C)(C(=O)OC)NC1=CC=C(C=C1)OC", "details": "", "is_desired": true}] | 180 | CELSIUS | null | null | 1-bromo-4-methoxybenzene (0.060 mL, 0.47 mmol), methyl 2-amino-2-methylpropanoate (0.05 g, 0.43 mmol), sodium 2-methylbutan-2-olate (0.052 g, 0.47 mmol), diacetoxypalladium (2.68 mg, 0.01 mmol) and methyl 2-(4-methoxyphenylamino)-2-methylpropanoate (0.00 µg) was added to a microwave vial. (TRIFLUOROMETHYL)-BENZENE (0.5... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CCC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].C1=CC=C(C=C1)C(F)(F)F | 180 | null | COC(=O)C(C)(C)N.COc1ccc(Br)cc1>CCC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].C1=CC=C(C=C1)C(F)(F)F>COC(=O)C(C)(C)Nc1ccc(OC)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d712f5c0551541748b4f06a98eb63af5 | COC(=O)C(C)(C)N.FC(F)(F)c1ccc(Cl)cc1>>COC(=O)C(C)(C)Nc1ccc(C(F)(F)F)cc1 | C1=CC(=CC=C1C(F)(F)F)Cl. CC(C)(C(=O)OC)N>>CC(C)(C(=O)OC)NC1=CC=C(C=C1)C(F)(F)F | [CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[NH2:8].Cl[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]1 | COC(=O)C(C)(C)N.FC(F)(F)c1ccc(Cl)cc1 | COC(=O)C(C)(C)Nc1ccc(C(F)(F)F)cc1 | CC(C)(C)[O-].[Na+] | CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd] | C1=CC=C(C=C1)C(F)(F)F | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH2;D1;+0:13]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CC(C)(C(=O)OC)NC1=CC=C(C=C1)C(F)(F)F", "details": "", "is_desired": true}] | 180 | CELSIUS | null | null | 1-chloro-4-(trifluoromethyl)benzene (0.068 mL, 0.51 mmol), methyl 2-amino-2-methylpropanoate (0.05 g, 0.43 mmol),BUTYLDI-1-ADAMANTYLPHOSPHINE (0.015 g, 0.04 mmol), sodium 2-methylpropan-2-olate (0.082 g, 0.85 mmol) and diacetoxypalladium (4.79 mg, 0.02 mmol) was added to a microwave vial. (TRIFLUOROMETHYL)-BENZENE (0.5... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].C1=CC=C(C=C1)C(F)(F)F | 180 | null | COC(=O)C(C)(C)N.FC(F)(F)c1ccc(Cl)cc1>CC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].C1=CC=C(C=C1)C(F)(F)F>COC(=O)C(C)(C)Nc1ccc(C(F)(F)F)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-adf0259dd1b4403cabef49044d700c84 | COC(=O)C(C)(C)N.Cc1ccc(Cl)cc1>>COC(=O)C(C)(C)Nc1ccc(C)cc1 | CC1=CC=C(C=C1)Cl. CC(C)(C(=O)OC)N>>CC1=CC=C(C=C1)NC(C)(C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[NH2:8].Cl[c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]1 | COC(=O)C(C)(C)N.Cc1ccc(Cl)cc1 | COC(=O)C(C)(C)Nc1ccc(C)cc1 | CC(C)(C)[O-].[Na+] | CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH2;D1;+0:13]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CC1=CC=C(C=C1)NC(C)(C)C(=O)OC", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | A flask was loaded with diacetoxypalladium (6.39 mg, 0.03 mmol), BUTYLDI-1-ADAMANTYLPHOSPHINE (0.020 g, 0.06 mmol), sodium 2-methylpropan-2-olate (0.164 g, 1.71 mmol) and methyl 2-amino-2-methylpropanoate (0.2 g, 1.71 mmol). The flask was evacuated and backfilled and toluene (5ml) and 1-chloro-4-methylbenzene (0.168 ml... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | COC(=O)C(C)(C)N.Cc1ccc(Cl)cc1>CC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COC(=O)C(C)(C)Nc1ccc(C)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4c19150105e34defaeb92ce9b0748e42 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 86.67 | [{"value": 86.67, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (5 g, 16.02 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (2.453 g, 17.62 mmol) and cesium carbonate (7.83 g, 24.03 mmol) were suspended in 1,4-dioxane (75 mL). Nitrogen was bubbled through mixture for 15 minutes. (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosp... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b46a6c49414741af865dab7a6fa19802 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 57.77 | [{"value": 57.77, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a stirred solution of 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (28 g, 89.70 mmol) in 1,4-dioxane (300 mL) were added 1-isopropyl-3-methyl-1H-pyrazol-5-amine (14.98 g, 107.64 mmol), cesium carbonate (43.8 g, 134.55 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.67 g, 8.07 mmol) and di... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9b3d4697078d49aaa1c7aef286254c96 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 36.49 | [{"value": 36.49, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and sodium 2-methylpropan-2-olate (92 mg, 0.96 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(dip... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4827dc1e98814e62bfa94e2e91e1efd1 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 47.02 | [{"value": 47.02, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and cesium carbonate (626 mg, 1.92 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (39.9 mg, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-41cdb2f97f5445aca97a2a002d0ddd58 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 36.87 | [{"value": 36.87, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and cesium carbonate (626 mg, 1.92 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (120 mg, 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0dc07c6e11344615900455301860696c | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 33.86 | [{"value": 33.86, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and cesium carbonate (313 mg, 0.96 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-327a3bfbd8b64cd3801bd5b8d317cb01 | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 45.14 | [{"value": 45.14, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (98 mg, 0.70 mmol) and cesium carbonate (626 mg, 1.92 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (39.9 mg, 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9669a589a7dc4055a27254e9fef3458e | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 47.78 | [{"value": 47.78, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (134 mg, 0.96 mmol) and cesium carbonate (626 mg, 1.92 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (39.9 mg, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7e62540b4ca7416d88222da262e8e74a | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl.CC1=NN(C(=C1)N)C(C)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]2)[c:28]([Cl:29])[cH:27][n:26]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH:23]([CH3:24])[CH3:25]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]... | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1 | CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 92.72 | [{"value": 92.72, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | dioxane (4.3 mL) was added to 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (142 mg, 0.45 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (127 mg, 0.91 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (52.6 mg, 0.09 mmol), BIS(DIBENZYLIDENEACETONE)PALLADIUM (39.2 mg, 0.07 mmol) and sodium 2-methyl... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1COCCO1 | 150 | null | CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-03f2f90229d7474393efca5188bac2c5 | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1>>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | CS(=O)(=O)C1=CC=C(C=C1)Br.C1=C(N=C(C=N1)Cl)N>>CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl | Br[c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:18][cH:17]1.[NH2:9][c:10]1[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]2)[cH:17][cH:18]1 | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1 | CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1):[c:4]:[c:5] | 70.39 | [{"value": 70.39, "product": "CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | 1-bromo-4-(methylsulfonyl)benzene (18.6 g, 79.12 mmol) then cesium carbonate (33.5 g, 102.85 mmol) were successively added to a solution of 6-chloropyrazin-2-amine (10.25 g, 79.12 mmol) in 1,4-dioxane (300 ml). The mixture was purged with nitrogen, then (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.75 g,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnccn1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 85 | null | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-db51fb4c9ca342c3a64870763aaddcf0 | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C(F)(F)F.Cn1cc(N)c(C(F)(F)F)n1>>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C(F)(F)F)ncc1C(F)(F)F | CN1C=C(C(=N1)C(F)(F)F)N.Cl.CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl>>CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CN(N=C3C(F)(F)F)C | Cl[c:14]1[cH:13][c:12]([NH:11][c:10]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]2)[c:28]([C:29]([F:30])([F:31])[F:32])[cH:27][n:26]1.[NH2:15][c:16]1[cH:17][n:18]([CH3:19])[n:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][c:12]1[cH:13][c:14]([... | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C(F)(F)F.Cn1cc(N)c(C(F)(F)F)n1 | CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C(F)(F)F)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14](-[NH2;D1;+0:15]):[c:16]:1>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14](-[NH;D2;+0:15]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[... | 60.42 | [{"value": 60.42, "product": "CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CN(N=C3C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.30 mmol), 1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-amine hydrochloride (122 mg, 0.61 mmol), cesium carbonate (247 mg, 0.76 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.1 mg, 0.05 mmol) and diacetoxypalladium (5.45 mg... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C(F)(F)F.Cn1cc(N)c(C(F)(F)F)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C(F)(F)F)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6eff375bd801443f9df865a891f3e022 | CN.FC(F)(F)c1cncc(Br)c1>>CNc1cncc(C(F)(F)F)c1 | C1=C(C=NC=C1Br)C(F)(F)F.CN>>CNC1=CN=CC(=C1)C(F)(F)F | [CH3:1][NH2:2].Br[c:3]1[cH:4][n:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1>>[CH3:1][NH:2][c:3]1[cH:4][n:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1 | CN.FC(F)(F)c1cncc(Br)c1 | CNc1cncc(C(F)(F)F)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 0 | [{"value": 0.0, "product": "CNC1=CN=CC(=C1)C(F)(F)F", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | 3-bromo-5-(trifluoromethyl)pyridine (100 mg, 0.44 mmol), methylamine 2 M in THF (0.442 mL, 0.88 mmol), and cesium carbonate (202 mg, 0.62 mmol) were suspended in dioxane (3 mL) . The reaction was purged with nitrogen for 30 minutes then 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (7.68 mg, 0.01 mmol) and TRIS(DIBEN... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].C1COCCO1 | 130 | null | CN.FC(F)(F)c1cncc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].C1COCCO1>CNc1cncc(C(F)(F)F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6058a506bcd3404d8683ad593ff991cd | CN.FC(F)(F)c1cncc(Br)c1>>CNc1cncc(C(F)(F)F)c1 | C1=C(C=NC=C1Br)C(F)(F)F.CN.Cl>>CNC1=CN=CC(=C1)C(F)(F)F | [CH3:1][NH2:2].Br[c:3]1[cH:4][n:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1>>[CH3:1][NH:2][c:3]1[cH:4][n:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1 | CN.FC(F)(F)c1cncc(Br)c1 | CNc1cncc(C(F)(F)F)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 0 | [{"value": 0.0, "product": "CNC1=CN=CC(=C1)C(F)(F)F", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | 3-bromo-5-(trifluoromethyl)pyridine (100 mg, 0.44 mmol), methylamine hydrochloride (59.8 mg, 0.88 mmol), and cesium carbonate (490 mg, 1.50 mmol) were suspended in dioxane (3 mL) . The reaction was purged with nitrogen for 30 minutes then 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (7.68 mg, 0.01 mmol) and TRIS(DIB... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].C1COCCO1 | 130 | null | CN.FC(F)(F)c1cncc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].C1COCCO1>CNc1cncc(C(F)(F)F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-dc9ab726462a4f469bd87d2f3adfc402 | CC(C)(C)OC(=O)N1CCNC(=O)C1.COc1cc(Cl)ccc1[N+](=O)[O-]>>COc1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)ccc1[N+](=O)[O-] | COC1=C(C=CC(=C1)Cl)[N+](=O)[O-].CC(C)(C)OC(=O)N1CCNC(=O)C1>>CC(C)(C)OC(=O)N1CCN(C(=O)C1)C2=CC(=C(C=C2)[N+](=O)[O-])OC | [NH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]1=[O:19].Cl[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:22]([N+:23](=[O:24])[O-:25])[cH:21][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]2=[O:19... | CC(C)(C)OC(=O)N1CCNC(=O)C1.COc1cc(Cl)ccc1[N+](=O)[O-] | COc1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)ccc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 8354026ab6bc63a1f8c04f4e18fe4ce6084ce50118b5fa6bb8e6ab57445e82b1 | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C1CNCCN1c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 68.39 | [{"value": 68.39, "product": "CC(C)(C)OC(=O)N1CCN(C(=O)C1)C2=CC(=C(C=C2)[N+](=O)[O-])OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A mixture of tert-butyl 3-oxopiperazine-1-carboxylate (100 mg, 0.50 mmol), 4-chloro-2-methoxy-1-nitrobenzene (94 mg, 0.50 mmol), cesium carbonate (244 mg, 0.75 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.34 mg, 0.03 mmol) and diacetoxypalladium (4.48 mg, 0.02 mmol) was dried for 15 min under HV... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amide | Tertiary amide | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CC(C)(C)OC(=O)N1CCNC(=O)C1.COc1cc(Cl)ccc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)ccc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ba7ec5906e7d4fb89a5c2ef7e7a905ac | CC(C)(C)OC(=O)N1CCNC(=O)C1.COc1cc(Cl)ccc1[N+](=O)[O-]>>COc1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)ccc1[N+](=O)[O-] | COC1=C(C=CC(=C1)Cl)[N+](=O)[O-].CC(C)(C)OC(=O)N1CCNC(=O)C1>>CC(C)(C)OC(=O)N1CCN(C(=O)C1)C2=CC(=C(C=C2)[N+](=O)[O-])OC | [NH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]1=[O:19].Cl[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:22]([N+:23](=[O:24])[O-:25])[cH:21][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]2=[O:19... | CC(C)(C)OC(=O)N1CCNC(=O)C1.COc1cc(Cl)ccc1[N+](=O)[O-] | COc1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)ccc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 8354026ab6bc63a1f8c04f4e18fe4ce6084ce50118b5fa6bb8e6ab57445e82b1 | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C1CNCCN1c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 100.3 | [{"value": 100.3, "product": "CC(C)(C)OC(=O)N1CCN(C(=O)C1)C2=CC(=C(C=C2)[N+](=O)[O-])OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A mixture of tert-butyl 3-oxopiperazine-1-carboxylate (1500 mg, 7.49 mmol), 4-chloro-2-methoxy-1-nitrobenzene (1405 mg, 7.49 mmol),cesium carbonate (3417 mg, 10.49 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (195 mg, 0.34 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (174 mg, 0.19 mmol)was dried ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amide | Tertiary amide | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 90 | null | CC(C)(C)OC(=O)N1CCNC(=O)C1.COc1cc(Cl)ccc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>COc1cc(N2CCN(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5a683960052443b49da1956ac277ce2a | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 | COCCOC1=CC(=CC(=C1)[N+](=O)[O-])I.C1COCCN1>>COCCOC1=CC(=CC(=C1)[N+](=O)[O-])N2CCOCC2 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.I[c:8]1[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:20][c:16]([N+:17](=[O:18])[O-:19])[cH:15]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1 | COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 16.14 | [{"value": 16.14, "product": "COCCOC1=CC(=CC(=C1)[N+](=O)[O-])N2CCOCC2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | diacetoxypalladium (0.136 g, 0.60 mmol) was added to a stirred mixture of 1-iodo-3-(2-methoxyethoxy)-5-nitrobenzene (3.9 g, 12.07 mmol), morpholine (1.373 mL, 15.69 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.225 g, 0.36 mmol) and cesium carbonate (11.80 g, 36.21 mmol) dissolved in toluene (100 mL) over a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-252a98ebb82d499dbf4cf33c53774e3f | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 | COCCOC1=CC(=CC(=C1)[N+](=O)[O-])I.C1COCCN1>>COCCOC1=CC(=CC(=C1)[N+](=O)[O-])N2CCOCC2 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.I[c:8]1[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:20][c:16]([N+:17](=[O:18])[O-:19])[cH:15]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1 | COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 91.56 | [{"value": 91.56, "product": "COCCOC1=CC(=CC(=C1)[N+](=O)[O-])N2CCOCC2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | diacetoxypalladium (0.087 g, 0.39 mmol) was added to a stirred mixture of 1-iodo-3-(2-methoxyethoxy)-5-nitrobenzene (2.5 g, 7.74 mmol), cesium carbonate (7.56 g, 23.21 mmol) and morpholine (0.880 mL, 10.06 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.482 g, 0.77 mmol) dissolved in toluene (80 mL) and dioxan... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ea00f60c7d1b4b2b96c954e87362056a | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 | COCCOC1=CC(=CC(=C1)[N+](=O)[O-])I.C1COCCN1>>COCCOC1=CC(=CC(=C1)[N+](=O)[O-])N2CCOCC2 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.I[c:8]1[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:20][c:16]([N+:17](=[O:18])[O-:19])[cH:15]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1 | COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 53.1 | [{"value": 53.1, "product": "COCCOC1=CC(=CC(=C1)[N+](=O)[O-])N2CCOCC2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The diacetoxypalladium (0.337 g, 1.50 mmol) was added to a stirred mixture of 1-iodo-3-(2-methoxyethoxy)-5-nitrobenzene (9.7 g, 30.02 mmol), cesium carbonate (29.3 g, 90.07 mmol) and morpholine (3.41 mL, 39.03 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (1.869 g, 3.00 mmol) dissolved in toluene (200 mL) and d... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-259872fd14244b3c874c12524fba3d75 | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12>>CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccc5c(=O)cc(N6CCOCC6)oc45)cccc3c2c1 | C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CC(C)(C)OC(=O)NC>>CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6 | [CH3:1][NH:2][C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].O=S(=O)(O[c:10]1[cH:11][cH:12][c:13]2[s:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][c:21]5[c:22](=[O:23])[cH:24][c:25]([N:26]6[CH2:27][CH2:28][O:29][CH2:30][CH2:31]6)[o:32][c:33]45)[cH:34][cH:35][cH:36][c:37]3[c:38]2[cH:39]1)C(F)(F)F>>[CH3:1][N:2]([C:3](=... | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12 | CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccc5c(=O)cc(N6CCOCC6)oc45)cccc3c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | c5e80da0d06f3aeb99dd8217a6e4cab413dca955dd9155f8444623e009bfc7d9 | 538b97a9a96524755fe1a26c80cb7b0d86358c2375f4cbbb7cc1f2a5981bff3a | O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccccc34)cccc12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;... | 34.93 | [{"value": 34.93, "product": "CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | 6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (207.4 mg, 0.37 mmol), tert-butyl methylcarbamate (194 mg, 1.48 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (10.69 mg, 0.02 mmol) and cesium carbonate (481 mg, 1.48 mmol) were suspended in dioxane (6 mL) and s... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Carbamic ester | Carbamic ester | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | c1ccc2ccccc2o1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e345842737b540bdabd050997047f016 | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12>>CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccc5c(=O)cc(N6CCOCC6)oc45)cccc3c2c1 | C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CC(C)(C)OC(=O)NC>>CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6 | [CH3:1][NH:2][C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].O=S(=O)(O[c:10]1[cH:11][cH:12][c:13]2[s:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][c:21]5[c:22](=[O:23])[cH:24][c:25]([N:26]6[CH2:27][CH2:28][O:29][CH2:30][CH2:31]6)[o:32][c:33]45)[cH:34][cH:35][cH:36][c:37]3[c:38]2[cH:39]1)C(F)(F)F>>[CH3:1][N:2]([C:3](=... | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12 | CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccc5c(=O)cc(N6CCOCC6)oc45)cccc3c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | c5e80da0d06f3aeb99dd8217a6e4cab413dca955dd9155f8444623e009bfc7d9 | 538b97a9a96524755fe1a26c80cb7b0d86358c2375f4cbbb7cc1f2a5981bff3a | O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccccc34)cccc12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;... | 66.94 | [{"value": 66.94, "product": "CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A solution of tert-butyl methylcarbamate (341 mg, 2.60 mmol) in dioxane (17.300 ml) was added to a stirred mixture of 6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (974 mg, 1.73 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (39.7 mg, 0.04 mmol), (9,9-dimethyl-9H-xanthene-4,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Carbamic ester | Carbamic ester | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | c1ccc2ccccc2o1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-33a377364ac14bd183dfd7eb0108a408 | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12>>CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccc5c(=O)cc(N6CCOCC6)oc45)cccc3c2c1 | C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CC(C)(C)OC(=O)NC>>CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6 | [CH3:1][NH:2][C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].O=S(=O)(O[c:10]1[cH:11][cH:12][c:13]2[s:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][c:21]5[c:22](=[O:23])[cH:24][c:25]([N:26]6[CH2:27][CH2:28][O:29][CH2:30][CH2:31]6)[o:32][c:33]45)[cH:34][cH:35][cH:36][c:37]3[c:38]2[cH:39]1)C(F)(F)F>>[CH3:1][N:2]([C:3](=... | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12 | CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccc5c(=O)cc(N6CCOCC6)oc45)cccc3c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | OtherReaction | c5e80da0d06f3aeb99dd8217a6e4cab413dca955dd9155f8444623e009bfc7d9 | 538b97a9a96524755fe1a26c80cb7b0d86358c2375f4cbbb7cc1f2a5981bff3a | O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccccc34)cccc12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;... | 100.38 | [{"value": 100.38, "product": "CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A solution of tert-butyl methylcarbamate (35.0 mg, 0.27 mmol) in dioxane (1.781 ml) was added to a stirred mixture of 6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (100 mg, 0.18 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (4.08 mg, 4.45 µmol), (9,9-dimethyl-9H-xanthene-4,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Carbamic ester | Carbamic ester | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | c1ccc2ccccc2o1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f3dd88e6019442749a56a95e7a33ac6e | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].CC(=O)N1CCNCC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | [NH:7]1[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]2)[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-] | COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 77.54 | [{"value": 77.54, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | diacetoxypalladium (0.116 g, 0.52 mmol) was added to a stirred mixture of 4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol), 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.449 g, 0.78 mmol) and cesium carbonate (4.21 g, 12.93 mmol) dissolved in dioxan... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-77e8bb12d76a4a1d94f2c62d1d96fda1 | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].CC(=O)N1CCNCC1>>CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | [NH:7]1[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11]([CH3:12])=[O:13])[CH2:14][CH2:15]2)[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-] | COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 85.85 | [{"value": 85.85, "product": "CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | diacetoxypalladium (2.322 g, 10.34 mmol) was added to a stirred suspension of 4-bromo-1-methoxy-2-nitrobenzene (30 g, 129.29 mmol), 1-(piperazin-1-yl)ethanone (16.57 g, 129.29 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (8.98 g, 15.52 mmol) and cesium carbonate (84 g, 258.59 mmol) dissolved in ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a7d27a030aca4653bd3b2b42172cb84b | CONC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CONC(=O)C1=CC=CC=C1N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].I[c:13]1[cH:14][c:15]([NH:16][c:17]2[cH:18][n:19]([CH3:20])[n:21][c:22]2[CH3:23])[n:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]2... | CONC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 74.87 | [{"value": 74.87, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.817 g, 3.14 mmol), diacetoxypalladium (0.353 g, 1.57 mmol), 2-amino-N-methoxybenzamide (8.87 g, 53.39 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (12 g, 31.40 mmol) and cesium carbonate (20.46 g, 62.81 mmol) were weighed ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4399ad74c4a84693a726596b8c6dc9ab | CONC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CONC(=O)C1=CC=CC=C1N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].I[c:13]1[cH:14][c:15]([NH:16][c:17]2[cH:18][n:19]([CH3:20])[n:21][c:22]2[CH3:23])[n:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17]2... | CONC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 48.99 | [{"value": 48.99, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.303 g, 0.52 mmol), diacetoxypalladium (0.059 g, 0.26 mmol), 2-amino-N-methoxybenzamide (1.479 g, 8.90 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (2 g, 5.23 mmol) and cesium carbonate (3.41 g, 10.47 mmol) were weighed out... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1ccccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2545e16c54de49a781f0868d26d7cb44 | CONC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.COC1=CC=CC(=C1C(=O)NOC)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH2:8])[cH:27][cH:28][cH:29][c:30]1[O:31][CH3:32].I[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][n:15]([CH3:16])[n:17][c:18]2[CH3:19])[n:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][n:15]... | CONC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 74.09 | [{"value": 74.09, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (34.1 mg, 0.06 mmol), diacetoxypalladium (7.93 mg, 0.04 mmol), 2-amino-N,6-dimethoxybenzamide (131 mg, 0.67 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol) and cesium carbonate (256 mg, 0.79 mmol) were weighe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1c(N)cccc1OC.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1c(Nc2cc(Nc3cn(C)nc3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0f54af454e1c49e3950d93f112c4112b | CNC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=C(C=CC=C1OC)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31].I[c:8]1[cH:9][c:10]([NH:11][c:12]2[cH:13][c:14]([CH3:15])[n:16][n:17]2[CH3:18])[n:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[cH:13][c:14]([CH3:15])[n... | CNC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 45.95 | [{"value": 45.95, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A suspension of 2-amino-6-methoxy-N-methylbenzamide (8.84 g, 49.07 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (12.5 g, 32.71 mmol), diacetoxypalladium (0.367 g, 1.64 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.893 g, 3.27 mmol) and cesium carbonate (19.18 g... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-62ffd954c4be4ad5b0533c19b263b236 | CNC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=C(C=CC=C1OC)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31].I[c:8]1[cH:9][c:10]([NH:11][c:12]2[cH:13][c:14]([CH3:15])[n:16][n:17]2[CH3:18])[n:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[cH:13][c:14]([CH3:15])[n... | CNC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 41.58 | [{"value": 41.58, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | 2-amino-6-methoxy-N-methylbenzamide (19.45 g, 107.95 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (27.5 g, 71.97 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.16 g, 7.20 mmol) diacetoxypalladium (0.808 g, 3.60 mmol) and cesium carbonate (42.2 g, 129.54 mmol) wer... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 95 | null | CNC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3925d0a898bc49db9d7ff1cb2ec90b8d | CC1c2ccc(Cl)nc2OC(C2CC2)CN1C.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3C)ccc1-c1cnn(C)c1 | CC1C2=C(N=C(C=C2)Cl)OC(CN1C)C3CC3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1C2=C(N=C(C=C2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)OC(CN1C)C5CC5 | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH:15]1[CH2:16][CH2:17]1)[CH2:18][N:19]([CH3:20])[CH:21]2[CH3:22].[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:23][cH:24][c:25]1-[c:26]1[cH:27][n:28][n:29]([CH3:30])[cH:31]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]([CH... | CC1c2ccc(Cl)nc2OC(C2CC2)CN1C.COc1nc(N)ccc1-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3C)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OC(C2CC2)CNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 15.27 | [{"value": 15.27, "product": "CC1C2=C(N=C(C=C2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)OC(CN1C)C5CC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-2-cyclopropyl-4,5-dimethyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (122 mg, 0.48 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (99 mg, 0.48 mmol), Pd2dba3 (11.05 mg, 0.01 mmol), BINAP (15.03 mg, 0.02 mmol) and SODIUM TERT-BUTOXIDE (69.6 mg, 0.72 mmol) were weighed in to a microwave vial, t... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccncc1.c1cnc2c(c1)C[NH]CCO2.C1CC1.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CC1c2ccc(Cl)nc2OC(C2CC2)CN1C.COc1nc(N)ccc1-c1cnn(C)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1nc(Nc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-996b98cdf02a43a3b340c4e4f981f563 | C1CNCCN1.Fc1cc(Br)ccc1OCc1ccccc1>>Fc1cc(N2CCNCC2)ccc1OCc1ccccc1 | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C1CNCCN1>>C1CN(CCN1)C2=CC(=C(C=C2)OCC3=CC=CC=C3)F | [NH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1.Br[c:4]1[cH:3][c:2]([F:1])[c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:12][cH:11]1>>[F:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[cH:11][cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | C1CNCCN1.Fc1cc(Br)ccc1OCc1ccccc1 | Fc1cc(N2CCNCC2)ccc1OCc1ccccc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 71.64 | [{"value": 71.64, "product": "C1CN(CCN1)C2=CC(=C(C=C2)OCC3=CC=CC=C3)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | sodium 2-methylpropan-2-olate (6.43 g, 66.88 mmol) was added to 1-(benzyloxy)-4-bromo-2-fluorobenzene (13.43 g, 47.77 mmol) and piperazine (24.69 g, 286.64 mmol) in toluene (140 mL). The resulting mixture was bubbled with nitrogen for 10 minutes then 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (2.97 g, 4.78 mmol) and T... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | C1CNCCN1.Fc1cc(Br)ccc1OCc1ccccc1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Fc1cc(N2CCNCC2)ccc1OCc1ccccc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-26b0abcb83694e11aba5d8cb57edf605 | CNC(=O)CN1CCOCC1.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>>CN(C(=O)CN1CCOCC1)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CNC(=O)CN1CCOCC1>>CN(C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6)C(=O)CN7CCOCC7 | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.O=S(=O)(O[c:12]1[cH:13][cH:14][c:15]2[s:16][c:17]3[c:18](-[c:19]4[cH:20][cH:21][cH:22][n:23]5[c:24](=[O:25])[cH:26][c:27]([N:28]6[CH2:29][CH2:30][O:31][CH2:32][CH2:33]6)[n:34][c:35]45)[cH:36][cH:37][cH:38][c:39]3[c:40]2[cH:41]1)C(F)(F)F>>[CH3:1... | CNC(=O)CN1CCOCC1.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12 | CN(C(=O)CN1CCOCC1)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Alkylation of amines | e52425da26c6d807074f7b38f990dc0bf487f798ff5c4971b6b28c7848a26596 | e8f1037ddf00c3008e109a885e9239c96953665a705783a27060bdf402b979e6 | O=C(CN1CCOCC1)Nc1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[C;D1;H3:12]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11](-[C;D1;H3:12])-[C:9](-[C:8])=[O;D1;H0:10]):[c:7]:[c:6]:1 | 0 | [{"value": 0.0, "product": "CN(C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6)C(=O)CN7CCOCC7", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A solution of 6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (100mg, 0.18 mmol) in dry dioxane (1 ml) was added to a stirred mixture of N-methyl-2-morpholinoacetamide (33.8 mg, 0.21 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (4.08 mg, 4.45 µmol), (9,9-dimet... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Secondary amide | Tertiary amide | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | C1COCC[NH]1.c1ccn2ccccc2n1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CNC(=O)CN1CCOCC1.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[... |
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