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-fbf696d6dcb34e7c9c731cbe586b831a | COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1>>COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1 | B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Cl)C(=O)OC.C1=CC=C(C=C1)N>>B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C(=O)OC | Cl[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:26][c:16]([B:17]2[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]2)[cH:15]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]([B:17]2[O:18][C:19]([... | COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1 | COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | 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] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccc(B3OCCO3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | 2.29 | [{"value": 2.29, "product": "B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | aniline (0.162 mL, 1.78 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (440mg, 1.48 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (13.59 mg, 0.01 mmol), tri- tert-butylphosphine (10.80 µL, 0.04 mmol) and potassium phosphate (441 mg, 2.08 mmol) in degassed DME (6 mL) at 20°C... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.[B]1OCCO1 | HCl | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].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].COCCOC | 100 | null | COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].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].COCCOC>COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7f4bd58c1e854ed5b839b01e20dd39d2 | COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1>>COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1 | B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Cl)C(=O)OC.C1=CC=C(C=C1)N>>B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C(=O)OC | Cl[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:26][c:16]([B:17]2[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]2)[cH:15]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]([B:17]2[O:18][C:19]([... | COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1 | COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | 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] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccc(B3OCCO3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | aniline (0.360 mL, 3.95 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (900 mg, 3.03 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (139 mg, 0.15 mmol), [Reactants] and potassium phosphate (1546 mg, 7.28 mmol) in degassed DME (10 mL) at 20°C under nitrogen. The reaction was ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.[B]1OCCO1 | HCl | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].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].COCCOC | 100 | null | COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].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].COCCOC>COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-74a05ca9ab9042dbb66a38d995757deb | Cc1c(Cl)c2cc(N)ccc2n1C.Cc1nn(-c2ccnc(Cl)n2)cc1CN1CC(O)C1>>Cc1nn(-c2ccnc(Nc3ccc4c(c3)c(Cl)c(C)n4C)n2)cc1CN1CC(O)C1 | CC1=NN(C=C1CN2CC(C2)O)C3=NC(=NC=C3)Cl.CC1=C(C2=C(N1C)C=CC(=C2)N)Cl>>CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)CN5CC(C5)O)Cl | [NH2:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[c:17]([Cl:18])[c:19]([CH3:20])[n:21]2[CH3:22].Cl[c:9]1[n:8][cH:7][cH:6][c:5](-[n:4]2[n:3][c:2]([CH3:1])[c:25]([CH2:26][N:27]3[CH2:28][CH:29]([OH:30])[CH2:31]3)[cH:24]2)[n:23]1>>[CH3:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[... | Cc1c(Cl)c2cc(N)ccc2n1C.Cc1nn(-c2ccnc(Cl)n2)cc1CN1CC(O)C1 | Cc1nn(-c2ccnc(Nc3ccc4c(c3)c(Cl)c(C)n4C)n2)cc1CN1CC(O)C1 | C(=O)([O-])[O-].[K+].[K+] | 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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(-n2cc(CN3CCC3)cn2)nc(Nc2ccc3[nH]ccc3c2)n1 | 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": "CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)CN5CC(C5)O)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A 40 mL scintillation vial charged with 3-chloro-1,2-dimethyl-1H-indol-5-amine (53.6 mg, 0.28 mmol), 1-((1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methyl)azetidin-3-ol (70mg, 0.25 mmol), palladium(II) acetate (2.81 mg, 0.01 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (x--phos) (11... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1c[nH]nc1.c1cncnc1.c1ccc2[nH]ccc2c1.C1C[NH]C1 | HCl | C(=O)([O-])[O-].[K+].[K+].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].C1COCCO1 | 100 | null | Cc1c(Cl)c2cc(N)ccc2n1C.Cc1nn(-c2ccnc(Cl)n2)cc1CN1CC(O)C1>C(=O)([O-])[O-].[K+].[K+].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].C1COCCO1>Cc1nn(-c2ccnc(Nc3ccc4c(c3)c(Cl)c(C)n4C)n2)cc1CN1CC(O)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7b12b51966524113889660895d5b1caa | C1CNCCN1.Clc1ccccc1Br>>Clc1ccccc1N1CCNCC1 | C1=CC=C(C(=C1)Cl)Br.C1CNCCN1>>C1CN(CCN1)C2=CC=CC=C2Cl | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.Br[c:7]1[c:2]([Cl:1])[cH:3][cH:4][cH:5][cH:6]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | C1CNCCN1.Clc1ccccc1Br | Clc1ccccc1N1CCNCC1 | 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(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[c:2]:[c:3] | 43.8 | [{"value": 43.8, "product": "C1CN(CCN1)C2=CC=CC=C2Cl", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To a stirred sol of 1-bromo-2-chlorobenzene (0.606 mL, 5.22 mmol) in toluene (10 mL) was added Pd2(dba)3 (0.239 g, 0.26 mmol), BINAP (0.163 g, 0.26 mmol), sodium tert-butoxide (0.753 g, 7.83 mmol) and piperazine (1.350 g, 15.67 mmol) and the resulting sol was heated at 110 °C for 16h. Cooled to rt, filtered through a ... | 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 | 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.Clc1ccccc1Br>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>Clc1ccccc1N1CCNCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bb7f6619ebed4436b7a7f09c9d4cd82e | C1CNCCN1.Clc1ccccc1Br>>Clc1ccccc1N1CCNCC1 | C1=CC=C(C(=C1)Cl)Br.C1CNCCN1>>C1CN(CCN1)C2=CC=CC=C2Cl | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.Br[c:7]1[c:2]([Cl:1])[cH:3][cH:4][cH:5][cH:6]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | C1CNCCN1.Clc1ccccc1Br | Clc1ccccc1N1CCNCC1 | 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(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[c:2]:[c:3] | 58.41 | [{"value": 58.41, "product": "C1CN(CCN1)C2=CC=CC=C2Cl", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To a stirred sol of 1-bromo-2-chlorobenzene (0.606 mL, 5.22 mmol) in toluene (10 mL) was added Pd2(dba)3 (0.239 g, 0.26 mmol), BINAP (0.163 g, 0.26 mmol), sodium tert-butoxide (0.753 g, 7.83 mmol) and piperazine (1.350 g, 15.67 mmol) and the resulting sol was heated at 110 °C for 16 h. Filtered through a celeite pad &... | 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 | 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.Clc1ccccc1Br>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>Clc1ccccc1N1CCNCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1e9ec853eb3e43adb71af85c977827e9 | Brc1ccc(Br)cc1.CC1CNC1>>CC1CN(c2ccc(Br)cc2)C1 | C1=CC(=CC=C1Br)Br.CC1CNC1>>CC1CN(C1)C2=CC=C(C=C2)Br | Br[c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.[CH3:1][CH:2]1[CH2:3][NH:4][CH2:12]1>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[CH2:12]1 | Brc1ccc(Br)cc1.CC1CNC1 | CC1CN(c2ccc(Br)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 | acd899655e2b0e86ceef4a9d181b61426359f3e69c77ab85f60116fcc1919812 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 84.74 | [{"value": 84.74, "product": "CC1CN(C1)C2=CC=C(C=C2)Br", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methylazetidine (0.5 g, 4.69 mmol), diacetoxypalladium (10.53 mg, 0.05 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.058 g, 0.09 mmol) and cesium carbonate (3.67 g, 11.26 mmol), degassed toluene (15 mL) were heated at 100 °C over the weekend. The RM was filtered and washed with EtOAc the filtrate was then con... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNC1 | C1C[NH]C1.c1ccccc1 | C1C[NH]C1.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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | Brc1ccc(Br)cc1.CC1CNC1>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>CC1CN(c2ccc(Br)cc2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4a5932c3579844d8b45d89bc150e08f1 | CCOC(=O)C1CC1C(=O)c1ncc(Br)cc1OC.Clc1ccc(NCC2CC2)c2ccccc12>>CCOC(=O)C1CC1C(=O)c1ncc(N(CC2CC2)c2ccc(Cl)c3ccccc23)cc1OC | CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)Br)OC.C1CC1CNC2=CC=C(C3=CC=CC=C32)Cl.Cl>>CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)N(CC3CC3)C4=CC=C(C5=CC=CC=C54)Cl)OC | Br[c:14]1[cH:13][n:12][c:11]([C:9]([CH:8]2[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]2)=[O:10])[c:32]([O:33][CH3:34])[cH:31]1.[NH:15]([CH2:16][CH:17]1[CH2:18][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([Cl:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH:8]1[C:9](=[O:10])... | CCOC(=O)C1CC1C(=O)c1ncc(Br)cc1OC.Clc1ccc(NCC2CC2)c2ccccc12 | CCOC(=O)C1CC1C(=O)c1ncc(N(CC2CC2)c2ccc(Cl)c3ccccc23)cc1OC | 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 | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1ccc(N(CC2CC2)c2cccc3ccccc23)cn1)C1CC1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:[c:8]:1 | 66.22 | [{"value": 66.22, "product": "CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)N(CC3CC3)C4=CC=C(C5=CC=CC=C54)Cl)OC", "details": "", "is_desired": true}] | 70 | CELSIUS | null | null | Repeat from Patent write up and cf _EN06741-39\Reaction_ **_Aim:-_ **to Prepare target for further use **. NB. the SM is either the (R,R) or (S,S) isomer** ethyl 2-(5-bromo-3-methoxypicolinoyl)cyclopropanecarboxylate (0.329 g, 1.00 mmol), 4-chloro-N-(cyclopropylmethyl)naphthalen-1-amine, HCl (0.323 g, 1.20 mmol), P... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1 | c1ccncc1 | C1CC1.c1ccncc1.C1CC1.c1ccc2ccccc2c1 | 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 | 70 | null | CCOC(=O)C1CC1C(=O)c1ncc(Br)cc1OC.Clc1ccc(NCC2CC2)c2ccccc12>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>CCOC(=O)C1CC1C(=O)c1ncc(N(CC2CC2)c2ccc(Cl)c3ccccc23)cc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2ea0e4e929e149198feaa40dbd6f469f | Brc1ccc2ccn(Cc3cccnc3)c2c1.CC(C)(C)OC(N)=O>>CC(C)(C)OC(=O)Nc1ccc2ccn(Cc3cccnc3)c2c1 | C1=CC(=CN=C1)CN2C=CC3=C2C=C(C=C3)Br.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3 | Br[c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][n:21][cH:22]3)[c:23]2[cH:24]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][n:21][c... | Brc1ccc2ccn(Cc3cccnc3)c2c1.CC(C)(C)OC(N)=O | CC(C)(C)OC(=O)Nc1ccc2ccn(Cc3cccnc3)c2c1 | 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.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 0ac5bbffa1fd97fc6d4d15dd2adcd3147c68122d9c2d02c9e07627174564e3f5 | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1cncc(Cn2ccc3ccccc32)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[c:6]:1):[#7;a:7](-[C:8]):[c:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[#8:14]-[C:15](-[NH2;D1;+0:16])=[O;D1;H0:17]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:16]-[C:15](=[O;D1;H0:17])-[#8:14]-[C:11](-[C;D1;H3:10])(-[C;D1;H3:12])-[C;... | 81.96 | [{"value": 81.96, "product": "CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | 6-bromo-1-(pyridin-3-ylmethyl)-1H-indole (1.3 g, 4.53 mmol), cesium carbonate (2.213 g, 6.79 mmol), tert-butyl carbamate (0.796 g, 6.79 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.453 g, 0.95 mmol) and PALLADIUM(II) ACETATE (0.071 g, 0.32 mmol) were placed under a nitrogen atmosphere. dry degass... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 110 | null | Brc1ccc2ccn(Cc3cccnc3)c2c1.CC(C)(C)OC(N)=O>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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CC(C)(C)OC(=O)Nc1ccc2ccn(Cc3cccnc3)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-09771da494274543af3440cf05022c0c | Brc1ccc2ccn(Cc3cccnc3)c2c1.CC(C)(C)OC(N)=O>>CC(C)(C)OC(=O)Nc1ccc2ccn(Cc3cccnc3)c2c1 | C1=CC(=CN=C1)CN2C=CC3=C2C=C(C=C3)Br.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3 | Br[c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][n:21][cH:22]3)[c:23]2[cH:24]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][n:21][c... | Brc1ccc2ccn(Cc3cccnc3)c2c1.CC(C)(C)OC(N)=O | CC(C)(C)OC(=O)Nc1ccc2ccn(Cc3cccnc3)c2c1 | 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.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 0ac5bbffa1fd97fc6d4d15dd2adcd3147c68122d9c2d02c9e07627174564e3f5 | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1cncc(Cn2ccc3ccccc32)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[c:6]:1):[#7;a:7](-[C:8]):[c:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[#8:14]-[C:15](-[NH2;D1;+0:16])=[O;D1;H0:17]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:16]-[C:15](=[O;D1;H0:17])-[#8:14]-[C:11](-[C;D1;H3:10])(-[C;D1;H3:12])-[C;... | 83.47 | [{"value": 83.47, "product": "CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-bromo-1-(pyridin-3-ylmethyl)-1H-indole (0.1 g, 0.35 mmol), cesium carbonate (0.170 g, 0.52 mmol), tert-butyl carbamate (0.061 g, 0.52 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.035 g, 0.07 mmol) and PALLADIUM(II) ACETATE (5.47 mg, 0.02 mmol) were placed under a nitrogen atmosphere. dry degass... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Brc1ccc2ccn(Cc3cccnc3)c2c1.CC(C)(C)OC(N)=O>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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CC(C)(C)OC(=O)Nc1ccc2ccn(Cc3cccnc3)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-521dd4e5c36647eca5936a0918a368fd | CCOC(=O)c1ccc(I)cc1.Nc1ccccc1Br>>CCOC(=O)c1ccc(Nc2ccccc2Br)cc1 | CCOC(=O)C1=CC=C(C=C1)I.C1=CC=C(C(=C1)N)Br>>CCOC(=O)C1=CC=C(C=C1)NC2=CC=CC=C2Br | I[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:19][cH:18]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[Br:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Br:17])[cH:18][cH:19]1 | CCOC(=O)c1ccc(I)cc1.Nc1ccccc1Br | CCOC(=O)c1ccc(Nc2ccccc2Br)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c: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](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 60.16 | [{"value": 60.16, "product": "CCOC(=O)C1=CC=C(C=C1)NC2=CC=CC=C2Br", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-Bromoaniline (1.851 mL, 16.35 mmol) and ethyl 4-iodobenzoate (2.60 mL, 15.58 mmol) were dissolved in toluene (argon bubbled through for 10 min) (80 mL). To the stirred mixture were palladium acetate (0.175 g, 0.78 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.776 g, 1.25 mmol) and cesium carbonate (7.10 g... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.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 | 100 | null | CCOC(=O)c1ccc(I)cc1.Nc1ccccc1Br>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>CCOC(=O)c1ccc(Nc2ccccc2Br)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a21d6ec12c02473a98dce7de6b637849 | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 | C1=CC(=CN=C1)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]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[cH:16][cH:17][cH:18][n:19][cH:20]1 | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C;D1;H3:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 0 | [{"value": 0.0, "product": "C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (9.34 mg, 0.04 mmol) and RuPhos (0.039 g, 0.08 mmol) were suspended in 1,4 dioxane (5 mL), degassed and stirred at 50 °C for 10 minutes. Then (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.100 g, 0.50 mmol), 3-bromopyridine (0.040 mL, 0.42 mmol) and cesium carbonate (0.203 g, 0.62 mmol) were adde... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d7d7e0dc4c0741f08ecfdb907acad13f | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 | C1=CC(=CN=C1)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]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[cH:16][cH:17][cH:18][n:19][cH:20]1 | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 | 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 | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C;D1;H3:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 0 | [{"value": 0.0, "product": "C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.145 g, 0.16 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.183 g, 0.32 mmol) were added to a mixture of Sodium tert-butoxide (0.912 g, 9.49 mmol), 3-bromopyridine (0.610 mL, 6.33 mmol),(R)-tert-butyl 3-methylpiperazine-1-carboxylate (1.901 g, 9.49 mmol) and tolu... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | 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 | 85 | null | Brc1cccnc1.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(C)(C)C)CCN1c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b33a6a5e9f314a52b92d41be195f749c | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 | C1=CC(=CN=C1)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]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[cH:16][cH:17][cH:18][n:19][cH:20]1 | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C;D1;H3:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 102.97 | [{"value": 102.97, "product": "C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | _Repeat of reaction EN05798-78_ Diacetoxypalladium (0.112 g, 0.50 mmol) and dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.466 g, 1.00 mmol) were dissolved in toluene (15 mL) at ambient temperature under nitrogen. The mixture was degassed and purged with nitrogen several times and heated to 50°C for 20 mi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-88ebd75900f542a9b6cc4c328b0f3d84 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-n1cnc(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]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... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-n1cnc(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5ccnc5)cn4)nc3O2)cc1 | 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] | 15.63 | [{"value": 15.63, "product": "CC1=CN(C=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (83 mg, 0.30 mmol) and 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (62.0 mg, 0.30 mmol) in DME (3 mL) was added to a microwave vial containing palladium(II) acetate (6.82 mg, 0.03 mmol), 2-(Dicyclohexylphosphino)biphen... | 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.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e2551fd8964c4f0a80ff232c25d61d8a | CC(C)(C)OC(N)=O.Cc1cnc(Cl)c(F)c1>>Cc1cnc(NC(=O)OC(C)(C)C)c(F)c1 | CC1=CC(=C(N=C1)Cl)F.CC(C)(C)OC(=O)N>>CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F | [NH2:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13].Cl[c:5]1[n:4][cH:3][c:2]([CH3:1])[cH:16][c:14]1[F:15]>>[CH3:1][c:2]1[cH:3][n:4][c:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]([F:15])[cH:16]1 | CC(C)(C)OC(N)=O.Cc1cnc(Cl)c(F)c1 | Cc1cnc(NC(=O)OC(C)(C)C)c(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.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | ed01b145192f9cffb3f3553513f8bbd15ca4f246fc1ccc0dad392a1f0f7069ce | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:14])-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 25.74 | [{"value": 25.74, "product": "CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (15.42 mg, 0.07 mmol) and(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (39.8 mg, 0.07 mmol) were added to a degassed mixture of 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol), tert-butyl carbamate (121 mg, 1.03 mmol) and cesium carbonate (336 mg, 1.03 mmol) in dioxane (10 mL) at 2... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | 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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CC(C)(C)OC(N)=O.Cc1cnc(Cl)c(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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1cnc(NC(=O)OC(C)(C)C)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fde5e0f95519439ca9660af435fc14a6 | CC(C)(C)OC(N)=O.Cc1cnc(Cl)c(F)c1>>Cc1cnc(NC(=O)OC(C)(C)C)c(F)c1 | CC1=CC(=C(N=C1)Cl)F.CC(C)(C)OC(=O)N>>CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F | [NH2:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13].Cl[c:5]1[n:4][cH:3][c:2]([CH3:1])[cH:16][c:14]1[F:15]>>[CH3:1][c:2]1[cH:3][n:4][c:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]([F:15])[cH:16]1 | CC(C)(C)OC(N)=O.Cc1cnc(Cl)c(F)c1 | Cc1cnc(NC(=O)OC(C)(C)C)c(F)c1 | [OH-].[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.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | ed01b145192f9cffb3f3553513f8bbd15ca4f246fc1ccc0dad392a1f0f7069ce | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:14])-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 25.74 | [{"value": 25.74, "product": "CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (15.42 mg, 0.07 mmol) and(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (39.8 mg, 0.07 mmol) were added to a degassed mixture of 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol), tert-butyl carbamate (105 mg, 0.89 mmol) and 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol) in di... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | [OH-].[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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CC(C)(C)OC(N)=O.Cc1cnc(Cl)c(F)c1>[OH-].[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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1cnc(NC(=O)OC(C)(C)C)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5545e57a105549059abb855326d6ce2b | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.Fc1cnc(Cl)cc1-c1cnn2c1CCCCC2>>CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(=O)Nc2cc(-c3cnn4c3CCCCC4)c(F)cn2)C1 | C1CCC2=C(C=NN2CC1)C3=CC(=NC=C3F)Cl.CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N>>CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCCN4N=C3)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[NH2:16])[CH2:34]1.Cl[c:17]1[cH:18][c:19](-[c:20]2[cH:21][n:22][n:23]3[c:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[c:30]([F:31])[cH:32][n:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:... | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.Fc1cnc(Cl)cc1-c1cnn2c1CCCCC2 | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(=O)Nc2cc(-c3cnn4c3CCCCC4)c(F)cn2)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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1cc(-c2cnn3c2CCCCC3)ccn1)C1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 72.45 | [{"value": 72.45, "product": "CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCCN4N=C3)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Tetrakis(triphenylphosphine)palladium(0) (0.304 g, 0.26 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepine (0.700 g, 2.63 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (0.638 g, 2.63 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.305 g, 0.53 mmol... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccncc1 | c1ccncc1 | C1CCCCC1.c1ccncc1.c1cc2n(n1)CCCCC2 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].C1COCCO1 | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.Fc1cnc(Cl)cc1-c1cnn2c1CCCCC2>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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6d4c20d55c834a949848dd34c3fa431d | Brc1ccc(Br)cc1.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(c2ccc(Br)cc2)CC1 | C1=CC(=CC=C1Br)Br.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(CC1)C2=CC=C(C=C2)Br | Br[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:17][CH2:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | Brc1ccc(Br)cc1.CCOC(=O)C1CCNCC1 | CCOC(=O)C1CCN(c2ccc(Br)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.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 | 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] | 59.1 | [{"value": 59.1, "product": "CCOC(=O)C1CCN(CC1)C2=CC=C(C=C2)Br", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | A suspension of ethyl piperidine-4-carboxylate (3.27 mL, 21.20 mmol), 1,4-dibromobenzene (5 g, 21.20 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.485 g, 0.53 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.990 g, 1.59 mmol) and Sodium Tert-Butoxide (2.444 g, 25.43 mmol) in anhydrous toluene (60 mL) was stir... | 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 | 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 | 85 | null | Brc1ccc(Br)cc1.CCOC(=O)C1CCNCC1>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>CCOC(=O)C1CCN(c2ccc(Br)cc2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cb0ae83e039e422babb6d81e64a4df69 | Brc1ccc(Br)cc1.COC(=O)C1CCNC1>>COC(=O)C1CCN(c2ccc(Br)cc2)C1 | C1=CC(=CC=C1Br)Br.COC(=O)C1CCNC1>>COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br | Br[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][NH:8][CH2:16]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16]1 | Brc1ccc(Br)cc1.COC(=O)C1CCNC1 | COC(=O)C1CCN(c2ccc(Br)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.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 | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-[C:13]-1 | 29.15 | [{"value": 29.15, "product": "COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | A suspension of methyl pyrrolidine-3-carboxylate (800 mg, 6.19 mmol), 1,4-dibromobenzene (1461 mg, 6.19 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (142 mg, 0.15 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (289 mg, 0.46 mmol) and Sodium Tert-Butoxide (714 mg, 7.43 mmol) in anhydrous toluene (30 mL) was stirr... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.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 | 85 | null | Brc1ccc(Br)cc1.COC(=O)C1CCNC1>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>COC(=O)C1CCN(c2ccc(Br)cc2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7673f35cb6ca4307811eaa7801ce679c | Brc1ccc(Br)cc1.COC(=O)C1CCNC1>>COC(=O)C1CCN(c2ccc(Br)cc2)C1 | C1=CC(=CC=C1Br)Br.COC(=O)C1CCNC1>>COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br | Br[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][NH:8][CH2:16]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16]1 | Brc1ccc(Br)cc1.COC(=O)C1CCNC1 | COC(=O)C1CCN(c2ccc(Br)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.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 | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-[C:13]-1 | 31.6 | [{"value": 31.6, "product": "COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | A suspension of methyl pyrrolidine-3-carboxylate (2.1 g, 16.26 mmol), 1,4-dibromobenzene (3.84 g, 16.26 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.372 g, 0.41 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.759 g, 1.22 mmol) and Sodium Tert-Butoxide (1.875 g, 19.51 mmol) in anhydrous toluene (60 mL) was s... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.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 | 85 | null | Brc1ccc(Br)cc1.COC(=O)C1CCNC1>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>COC(=O)C1CCN(c2ccc(Br)cc2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d3fce1c8e3204b57a80e5c0d53c5c1f7 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(NC(C)=O)cc1Br>>COc1ccc(NC(C)=O)cc1N1CCNCC1 | CC(=O)NC1=CC(=C(C=C1)OC)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(=O)NC1=CC(=C(C=C1)OC)N2CCNCC2 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][NH:13][CH2:18][CH2:17]1.Br[c:12]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[cH:11][c:12]1[N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(NC(C)=O)cc1Br | COc1ccc(NC(C)=O)cc1N1CCNCC1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 1155a782af40ddd9c7c7ab45b40bc8450f26a553a41c0f0d5dfec075d80a69f3 | 4692e9cfac8ca0f49eb5c33838ae1fa5c1a375a44556f0da8885d569da661aa1 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[NH;D2;+0:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 50.91 | [{"value": 50.91, "product": "CC(=O)NC1=CC(=C(C=C1)OC)N2CCNCC2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of N-(3-bromo-4-methoxyphenyl)acetamide (0.5 g, 2.05 mmol) dissolved in toluene (5 mL) was treated with tert-butyl piperazine-1-carboxylate (0.382 g, 2.05 mmol), diacetoxypalladium (0.046 g, 0.20 mmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.191 g, 0.41 mmol) and sodium 2-methylpropan-2-ol... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | C1C[NH]CCN1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(NC(C)=O)cc1Br>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1ccc(NC(C)=O)cc1N1CCNCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-00b630fb849d46988bc61ed1eeecad73 | CN1CCN(Cc2cccc(N)c2)CC1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1>>Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(CN3CCN(C)CC3)c2)nc1 | CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl.CN1CCN(CC1)CC2=CC(=CC=C2)N>>CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)NC5=CC=CC(=C5)CN6CCN(CC6)C | [NH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]([CH2:34][N:35]2[CH2:36][CH2:37][N:38]([CH3:39])[CH2:40][CH2:41]2)[cH:42]1.Cl[c:27]1[cH:26][cH:25][c:24]([C:22]([NH:21][c:20]2[c:2]([CH3:1])[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[O:15][CH2:16][CH2:17][O:18]4)[cH:19]2)=[O:23])[cH:44][n:4... | CN1CCN(Cc2cccc(N)c2)CC1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1 | Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(CN3CCN(C)CC3)c2)nc1 | 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 | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1cccc(NC(=O)c2ccc3c(c2)OCCO3)c1)c1ccc(Nc2cccc(CN3CCNCC3)c2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | 25.89 | [{"value": 25.89, "product": "CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)NC5=CC=CC(=C5)CN6CCN(CC6)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A mixture of 6-chloro-N-(5-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-methylphenyl)nicotinamide (50 mg, 0.12 mmol),3-((4-methylpiperazin-1-yl)methyl)aniline (36.3 mg, 0.18 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.10 mg, 7.08 µmol),TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (3.24 mg, 3.54 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2c(c1)OCCO2.c1ccncc1.c1ccccc1.C1C[NH]CC[NH]1 | 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].CC1=CC=CC=C1 | 100 | null | CN1CCN(Cc2cccc(N)c2)CC1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1>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=... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ff2be4fb066f4702ab3412c6fd0e670a | Brc1cccc(I)c1.NCC1CCOCC1>>Brc1cccc(NCC2CCOCC2)c1 | C1=CC(=CC(=C1)I)Br.C1COCCC1CN>>C1COCCC1CNC2=CC(=CC=C2)Br | I[c:6]1[cH:5][cH:4][cH:3][c:2]([Br:1])[cH:15]1.[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][CH2:8][CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1 | Brc1cccc(I)c1.NCC1CCOCC1 | Brc1cccc(NCC2CCOCC2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2CCOCC2)cc1 | 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] | 30.98 | [{"value": 30.98, "product": "C1COCCC1CNC2=CC(=CC=C2)Br", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Palladium (II) acetate (14.28 mg, 0.06 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (79 mg, 0.13 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 1-bromo-3-iodobenzene (240 mg, 0.85 mmol), (tetrahydro-2H-pyran-4-yl)me... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCOCC1 | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | Brc1cccc(I)c1.NCC1CCOCC1>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>Brc1cccc(NCC2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6368febfb34940ba908b28066b8fb22a | COC(=O)c1cc(Br)cc(I)c1.Nc1ccccc1>>COC(=O)c1cc(Br)cc(Nc2ccccc2)c1 | COC(=O)C1=CC(=CC(=C1)I)Br.C1=CC=C(C=C1)N>>COC(=O)C1=CC(=CC(=C1)Br)NC2=CC=CC=C2 | I[c:10]1[cH:9][c:7]([Br:8])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | COC(=O)c1cc(Br)cc(I)c1.Nc1ccccc1 | COC(=O)c1cc(Br)cc(Nc2ccccc2)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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:[c:8] | 40.51 | [{"value": 40.51, "product": "COC(=O)C1=CC(=CC(=C1)Br)NC2=CC=CC=C2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | diacetoxypalladium (0.314 g, 1.40 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.871 g, 1.40 mmol) were added to a degassed mixture of methyl 3-bromo-5-iodobenzoate (4.77 g, 13.99 mmol), aniline (2.55 ml, 13.99 mmol) and cesium carbonate (3.87 g, 11.89 mmol) in toluene (137 ml) under nitrogen. The resulting m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.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 | 110 | null | COC(=O)c1cc(Br)cc(I)c1.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>COC(=O)c1cc(Br)cc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4389cfc2af664ae3968b09023440510c | Clc1ccnc(Nc2ccccc2)c1.NCc1cccnc1>>c1ccc(Nc2cc(NCc3cccnc3)ccn2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC(=CN=C1)CN>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CN=CC=C3 | Cl[c:8]1[cH:7][c:6]([NH:5][c:4]2[cH:3][cH:2][cH:1][cH:21][cH:20]2)[n:19][cH:18][cH:17]1.[NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[cH:17][cH:18][n:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1cccnc1 | c1ccc(Nc2cc(NCc3cccnc3)ccn2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NCc3cccnc3)ccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[#7;a:8]:[c:9]:[c:10]-[C:11]-[NH2;D1;+0:12]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[c:10]:[c:9]:[#7;a:8]):[c:7]:1 | 59.25 | [{"value": 59.25, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CN=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Pyridin-3-ylmethanamine (58.1 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccncc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1cccnc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)N(C)C>c1ccc(Nc2cc(NCc3cccnc3)ccn2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3648f11ef3b2438f8cb66069ce02004a | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2ncc(-c3cc(Cl)ncc3F)n2C1>>CC1(C)Cc2ncc(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)n2C1 | CC1(CC2=NC=C(N2C1)C3=CC(=NC=C3F)Cl)C.CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N>>CC1(CC2=NC=C(N2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C | [NH2:12][C:13](=[O:14])[C@H:15]1[CH2:16][CH2:17][CH2:18][C@@H:19]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28]1.Cl[c:11]1[cH:10][c:9](-[c:8]2[cH:7][n:6][c:5]3[n:33]2[CH2:34][C:2]([CH3:1])([CH3:3])[CH2:4]3)[c:31]([F:32])[cH:30][n:29]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[n:6][cH:7][c:8](-[c:9]... | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2ncc(-c3cc(Cl)ncc3F)n2C1 | CC1(C)Cc2ncc(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)n2C1 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1cc(-c2cnc3n2CCC3)ccn1)C1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 80.01 | [{"value": 80.01, "product": "CC1(CC2=NC=C(N2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Tetrakis(triphenylphosphine)palladium(0) (43.5 mg, 0.04 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-6,6-dimethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (100 mg, 0.38 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (109 mg, 0.45 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.6 mg, 0.08... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccncc1 | c1ccncc1 | c1cn2c(n1)CCC2.c1ccncc1.C1CCCCC1 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].C1COCCO1 | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2ncc(-c3cc(Cl)ncc3F)n2C1>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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4d540317a2f04c1c94f4d355d5594da0 | CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br>>CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1 | CC1=CC(=NC=C1Br)Cl.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(CC1)C2=CN=C(C=C2C)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:18][CH2:19]1.Br[c:10]1[cH:11][n:12][c:13]([Cl:14])[cH:15][c:16]1[CH3:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][n:12][c:13]([Cl:14])[cH:15][c:16]2[CH3:17])[CH2:18][CH2:19]1 | CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br | CCOC(=O)C1CCN(c2cnc(Cl)cc2C)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 | 10c6f9b26f855d26243e4771b69ba961e55fa770e633c60af6779c5e67cf6f43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCCCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7])-[C:11]-[C:12] | 0 | [{"value": 0.0, "product": "CCOC(=O)C1CCN(CC1)C2=CN=C(C=C2C)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.18 mg, 0.02 mmol) was added to a degassed mixture of ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)(xantphos) (28.0 mg, 0.05 mmol) and ethyl 1-(6-chloro-4-methylpyridin-3-yl)piperidine-4-carboxylate and sodium ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | 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 | 100 | null | CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br>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>CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e4f50ecc5cb146dc9c3dbbd5fbb158a0 | CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br>>CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1 | CC1=CC(=NC=C1Br)Cl.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(CC1)C2=CN=C(C=C2C)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:18][CH2:19]1.Br[c:10]1[cH:11][n:12][c:13]([Cl:14])[cH:15][c:16]1[CH3:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][n:12][c:13]([Cl:14])[cH:15][c:16]2[CH3:17])[CH2:18][CH2:19]1 | CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br | CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 10c6f9b26f855d26243e4771b69ba961e55fa770e633c60af6779c5e67cf6f43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCCCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7])-[C:11]-[C:12] | 0 | [{"value": 0.0, "product": "CCOC(=O)C1CCN(CC1)C2=CN=C(C=C2C)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of diacetoxypalladium (10.87 mg, 0.05 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (45.2 mg, 0.10 mmol) dissolved in toluene (3 mL) was degassed and heated to 50°C for 30 minutes before adding ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), 5-bromo-2-chloro-4-methylpyridine ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a239c4c440984f189e32398ca38ff650 | COc1ccccc1CN.Clc1ccnc(Nc2ccccc2)c1>>COc1ccccc1CNc1ccnc(Nc2ccccc2)c1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.COC1=CC=CC=C1CN>>COC1=CC=CC=C1CNC2=CC(=NC=C2)NC3=CC=CC=C3 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][NH2:10].Cl[c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][NH:10][c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1 | COc1ccccc1CN.Clc1ccnc(Nc2ccccc2)c1 | COc1ccccc1CNc1ccnc(Nc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 60.32 | [{"value": 60.32, "product": "COC1=CC=CC=C1CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (2-methoxyphenyl)methanamine (73.7 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | COc1ccccc1CN.Clc1ccnc(Nc2ccccc2)c1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>COc1ccccc1CNc1ccnc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c4c7e21fb7f64c3192ea9f0c19be9329 | COc1ccccc1CN.Clc1ccnc(Nc2ccccc2)c1>>COc1ccccc1CNc1ccnc(Nc2ccccc2)c1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.COC1=CC=CC=C1CN>>COC1=CC=CC=C1CNC2=CC(=NC=C2)NC3=CC=CC=C3 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][NH2:10].Cl[c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][NH:10][c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1 | COc1ccccc1CN.Clc1ccnc(Nc2ccccc2)c1 | COc1ccccc1CNc1ccnc(Nc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 10.72 | [{"value": 10.72, "product": "COC1=CC=CC=C1CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (2-methoxyphenyl)methanamine (73.7 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | COc1ccccc1CN.Clc1ccnc(Nc2ccccc2)c1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>COc1ccccc1CNc1ccnc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1c5be4d17d4d4231816c56243b381f3c | COc1ccc(Nc2cc(Cl)ccn2)cc1.NCc1ccccc1>>COc1ccc(Nc2cc(NCc3ccccc3)ccn2)cc1 | COC1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>COC1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=CC=C3 | Cl[c:10]1[cH:9][c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23][cH:22]2)[n:21][cH:20][cH:19]1.[NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][n:21]2)[cH:22][cH:23]1 | COc1ccc(Nc2cc(Cl)ccn2)cc1.NCc1ccccc1 | COc1ccc(Nc2cc(NCc3ccccc3)ccn2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 59.17 | [{"value": 59.17, "product": "COC1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (50.2 mg, 0.47 mmol), 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (100 mg, 0.43 mmol) and sodium 2-methylpropan-2-olate (82 mg, 0.85 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSP... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | COc1ccc(Nc2cc(Cl)ccn2)cc1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>COc1ccc(Nc2cc(NCc3ccccc3)ccn2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e7d99d2977b74881941c52721ae6fed1 | Cc1c(Cl)c2cc(N)ccc2n1C.Cc1nn(-c2ccnc(Cl)n2)cc1C=O>>Cc1nn(-c2ccnc(Nc3ccc4c(c3)c(Cl)c(C)n4C)n2)cc1C=O | CC1=NN(C=C1C=O)C2=NC(=NC=C2)Cl.CC1=C(C2=C(N1C)C=CC(=C2)N)Cl>>CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)C=O)Cl | [NH2:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[c:17]([Cl:18])[c:19]([CH3:20])[n:21]2[CH3:22].Cl[c:9]1[n:8][cH:7][cH:6][c:5](-[n:4]2[n:3][c:2]([CH3:1])[c:25]([CH:26]=[O:27])[cH:24]2)[n:23]1>>[CH3:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:15]([cH:16]3)[c:17]([Cl:18])[c:1... | Cc1c(Cl)c2cc(N)ccc2n1C.Cc1nn(-c2ccnc(Cl)n2)cc1C=O | Cc1nn(-c2ccnc(Nc3ccc4c(c3)c(Cl)c(C)n4C)n2)cc1C=O | C(=O)([O-])[O-].[K+].[K+] | 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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnn(-c2ccnc(Nc3ccc4[nH]ccc4c3)n2)c1 | 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] | 64.6 | [{"value": 64.6, "product": "CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)C=O)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A 40 mL scintillation vial charged with 3-chloro-1,2-dimethyl-1H-indol-5-amine (192 mg, 0.99 mmol), 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde (200mg, 0.90 mmol), palladium(II) acetate (10.08 mg, 0.04 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (x--phos) (42.8 mg, 0.09 m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1c[nH]nc1.c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | C(=O)([O-])[O-].[K+].[K+].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].C1COCCO1 | 100 | null | Cc1c(Cl)c2cc(N)ccc2n1C.Cc1nn(-c2ccnc(Cl)n2)cc1C=O>C(=O)([O-])[O-].[K+].[K+].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].C1COCCO1>Cc1nn(-c2ccnc(Nc3ccc4c(c3)c(Cl)c(C)n4C)n2)cc1C=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d1c1c91e4e404216818f2894a49b5c96 | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1>>C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl | C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N.C(=O)(C(F)(F)F)O.C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl>>C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F | [CH3:1][C@H:2]1[CH2:3][C@H:4]([NH2:5])[CH2:19][CH2:20][N:21]1[C:22](=[O:23])[c:24]1[cH:25][n:26][n:27]([CH3:28])[c:29]1[Cl:30].Cl[c:6]1[cH:7][c:8](=[O:9])[nH:10][c:11]2[cH:12][c:13]([F:14])[c:15]([F:16])[cH:17][c:18]12>>[CH3:1][C@H:2]1[CH2:3][C@H:4]([NH:5][c:6]2[cH:7][c:8](=[O:9])[nH:10][c:11]3[cH:12][c:13]([F:14])[c:1... | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1 | C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl | 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) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1cn[nH]c1)N1CCC(Nc2cc(=O)[nH]c3ccccc23)CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:13] | 49.46 | [{"value": 49.46, "product": "C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | 4-chloro-6,7-difluoroquinolin-2(1H)-one (100 mg, 0.46 mmol) was taken in a microwave tube. Added ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone 2,2,2-trifluoroacetate (172 mg, 0.46 mmol), followed by the addition of Palladium (II) acetate (10.41 mg, 0.05 mmol), racemic-2,2'-Bis(dip... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.c1cn[nH]c1 | 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].CC1=CC=CC=C1 | 140 | null | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1>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>C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-eddc21aec4f145cea425a3b68c05d6df | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1>>C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl | C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N.C(=O)(C(F)(F)F)O.C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl>>C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F | [CH3:1][C@H:2]1[CH2:3][C@H:4]([NH2:5])[CH2:19][CH2:20][N:21]1[C:22](=[O:23])[c:24]1[cH:25][n:26][n:27]([CH3:28])[c:29]1[Cl:30].Cl[c:6]1[cH:7][c:8](=[O:9])[nH:10][c:11]2[cH:12][c:13]([F:14])[c:15]([F:16])[cH:17][c:18]12>>[CH3:1][C@H:2]1[CH2:3][C@H:4]([NH:5][c:6]2[cH:7][c:8](=[O:9])[nH:10][c:11]3[cH:12][c:13]([F:14])[c:1... | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1 | C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl | 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) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1cn[nH]c1)N1CCC(Nc2cc(=O)[nH]c3ccccc23)CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:13] | 23.08 | [{"value": 23.08, "product": "C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone 2,2,2-trifluoroacetate (1548 mg, 4.17 mmol) was taken in a 100ml single necked flask equipped with a reflux condenser connected to nitrogen source. Added 4-chloro-6,7-difluoroquinolin-2(1H)-one (600 mg, 2.78 mmol), followed by the addi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.c1cn[nH]c1 | 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].CC1=CC=CC=C1 | 140 | null | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1>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>C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-380656799acb406cac72f27fec617ff6 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccc(F)cc1>>Fc1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC(=CC=C1CN)F>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=C(C=C3)F | Cl[c:8]1[cH:9][cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20]1.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:21][cH:22]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][c:8]2[cH:9][cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20]2)[cH:21][cH:22]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccc(F)cc1 | Fc1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 60 | [{"value": 60.0, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=C(C=C3)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (4-fluorophenyl)methanamine (67.3 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSP... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccc(F)cc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Fc1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c4dfba23f3204e1a90cbbf5ad1b6ca0b | COc1ccc(Br)cc1.NCC1CCOCC1>>COc1ccc(NCC2CCOCC2)cc1 | COC1=CC=C(C=C1)Br.C1COCCC1CN>>COC1=CC=C(C=C1)NCC2CCOCC2 | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][cH:15]1.[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | COc1ccc(Br)cc1.NCC1CCOCC1 | COc1ccc(NCC2CCOCC2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2CCOCC2)cc1 | Br-[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] | 22.82 | [{"value": 22.82, "product": "COC1=CC=C(C=C1)NCC2CCOCC2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Palladium (II) acetate (0.090 g, 0.40 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.464 g, 0.80 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 1-bromo-4-methoxybenzene (1 g, 5.35 mmol), (tetrahydro-2H-pyran-... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCOCC1 | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | COc1ccc(Br)cc1.NCC1CCOCC1>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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1ccc(NCC2CCOCC2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6ec08990002f44da89217320c1b9e8f7 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 13.23 | [{"value": 13.23, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. 2-Dicyclohexylphosphino-2',6'-di- i-propoxy-1,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-34a984f4da874bc6bcf03a1eda073eec | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 6.32 | [{"value": 6.32, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimetho... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ca21e23d9a8e4bdaa490a5abf62f7063 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 53.81 | [{"value": 53.81, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROC... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9f517fc394904161a1e1cc39959a4dbc | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 63.1 | [{"value": 63.1, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (84 mg, 0.78 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCEN... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e3d2333fa0e548d69e486a455cc155f4 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 36.87 | [{"value": 36.87, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimetho... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5536c4f8409a4be1989b2939dc8c1cbe | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 41.99 | [{"value": 41.99, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimetho... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a3160d640f594550bd2649e07be8658f | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 4.83 | [{"value": 4.83, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. 2-Dicyclohexylphosphino-2',6'-di- i-propoxy-1,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-101cdc30e8364adba8cbaa6b2be6e3e8 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 49.35 | [{"value": 49.35, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol)-diacetoxypalladium (8.78 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2.00 mL) and ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-edb6c9cf54a940259581c192883091b5 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 69.12 | [{"value": 69.12, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROC... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e2437538f4f34f1fbc2e869de8f1a2bb | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 57.01 | [{"value": 57.01, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol)-diacetoxypalladium (8.78 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2.00 mL) and ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7f46e7191dbd43e493e0ec8cf7b58457 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 72.84 | [{"value": 72.84, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROC... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fa6dd91ea9f54dd39e4d31da62d4aa71 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 9.81 | [{"value": 9.81, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Phenylmethanamine (144 mg, 1.34 mmol), 4-chloro-N-phenylpyridin-2-amine (250 mg, 1.22 mmol)-diacetoxypalladium (21.94 mg, 0.10 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (81 mg, 0.15 mmol) and sodium 2-methylpropan-2-olate (235 mg, 2.44 mmol) were suspended in DMA (2.50 mL) in a ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 80 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-63156f7134e84c509ea49c365b3cf954 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1 | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:2]:1 | 5.65 | [{"value": 5.65, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol)-diacetoxypalladium (8.78 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2.00 mL) in a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0c726797efaf4f12802e1de309e7f336 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.COc1ccccc1Br>>COc1ccccc1N1C[C@@H]2C[C@H]1CN2C(=O)OC(C)(C)C | COC1=CC=CC=C1Br.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CC=CC=C3OC | [NH:9]1[CH2:10][C@@H:11]2[CH2:12][C@H:13]1[CH2:14][N:15]2[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22].Br[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][C@@H:11]2[CH2:12][C@H:13]1[CH2:14][N:15]2[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[C... | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.COc1ccccc1Br | COc1ccccc1N1C[C@@H]2C[C@H]1CN2C(=O)OC(C)(C)C | 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 | 258c5b04e0fe5ff2b16127382c7952c4ec596f1aa514957676849803665380ba | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2C[C@@H]3C[C@H]2CN3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[#7:7]1-[C:8]-[C:9]2-[C:10]-[C:11]-1-[C:12]-[NH;D2;+0:13]-2>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]2-[#7:7]-[C:8]-[C:9]-1-[C:10]-2):[c:2]:[c:3] | 68.91 | [{"value": 68.91, "product": "CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CC=CC=C3OC", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.063 g, 0.10 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (24.91 ml) was added and the resulting mixture heated to 50°C for 10 minutes. In a second reaction vessel wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1N[C@@H]2C[NH][C@H]1C2.c1ccccc1 | C1[NH][C@@H]2C[NH][C@H]1C2.c1ccccc1 | C1[NH][C@@H]2C[NH][C@H]1C2.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 | 105 | null | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.COc1ccccc1Br>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>COc1ccccc1N1C[C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-398e791076cd44778e3b80090d8d8371 | C1CCNCC1.O=C(O)c1ccc(Br)c(Cl)c1>>O=C(O)c1ccc(N2CCCCC2)c(Cl)c1 | C1=CC(=C(C=C1C(=O)O)Cl)Br.C1CCNCC1>>C1CCN(CC1)C2=C(C=C(C=C2)C(=O)O)Cl | [NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.Br[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:16][c:14]1[Cl:15]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]([Cl:15])[cH:16]1 | C1CCNCC1.O=C(O)c1ccc(Br)c(Cl)c1 | O=C(O)c1ccc(N2CCCCC2)c(Cl)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 | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[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] | 10 | [{"value": 10.0, "product": "C1CCN(CC1)C2=C(C=C(C=C2)C(=O)O)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | 4-bromo-3-chlorobenzoic acid (0.353 g, 1.5 mmol), piperidine (0.234 mL, 2.25 mmol), and sodium tert-butoxide (0.216 g, 2.25 mmol) were stirred together under N2 and heated to 80 °C. Pd2(dba)3 (0.014 g, 0.015 mmol), and BINAP (0.031 g, 0.05 mmol) were mixed in toluene (2 mL) and then added to the mixture and stirred at ... | 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+].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 | 80 | null | C1CCNCC1.O=C(O)c1ccc(Br)c(Cl)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>O=C(O)c1ccc(N2CCCCC2)c(Cl)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c0d27ca6d70a4e629ed6ea0a3371d1c9 | Brc1ccc2cn[nH]c2c1.C1CCNC1>>c1cc2cn[nH]c2cc1N1CCCC1 | C1=CC2=C(C=C1Br)NN=C2.C1CCNC1>>C1CCN(C1)C2=CC3=C(C=C2)C=NN3 | Br[c:9]1[cH:1][cH:2][c:3]2[cH:4][n:5][nH:6][c:7]2[cH:8]1.[NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1>>[cH:1]1[cH:2][c:3]2[cH:4][n:5][nH:6][c:7]2[cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | Brc1ccc2cn[nH]c2c1.C1CCNC1 | c1cc2cn[nH]c2cc1N1CCCC1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C([C-]=C1)CCN.[Cl-].[Pd+2] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b45ce8f725e8c9910bd223583be43187ad14594614a87aa33181dfb117bb81cf | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc2cn[nH]c2cc1N1CCCC1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:2:[c:9]:1.[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:6]1:[#7;a:7]:[c:8]2:[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]:[c:4]:2:[c:5]:1 | 93.74 | [{"value": 93.74, "product": "C1CCN(C1)C2=CC3=C(C=C2)C=NN3", "details": "", "is_desired": true}] | 60 | CELSIUS | null | null | _This reaction is done in triplicate_ : 6-bromo-1H-indazole (1.2 g, 6.09 mmol, 1 eq each), chloro(2-dicyclohexylphosphino-2',6'-di-i- propoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t- butylether adduct (RuPhos-PreCatalyst) (89 mg, 0.12 mmol, 0.02 eq each), 2-Dicyclohexylphosphino-2',6'-di-i-propox... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2n[nH]cc2c1.C1CCNC1 | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HBr | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C([C-]=C1)CCN.[Cl-].[Pd+2].C1CCOC1 | 60 | null | Brc1ccc2cn[nH]c2c1.C1CCNC1>[Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C([C-]=C1)CCN.[Cl-].[Pd+2].C1CCOC1>c1cc2cn[nH]c2cc1N1CCCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-775ba0e2a4c14f008f392711cc2a587a | CN1CCNCC1.Cn1nc(Br)nc1Br>>CN1CCN(c2nc(Br)nn2C)CC1 | CN1C(=NC(=N1)Br)Br.CN1CCNCC1>>CN1CCN(CC1)C2=NC(=NN2C)Br | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:13][CH2:14]1.Br[c:6]1[n:7][c:8]([Br:9])[n:10][n:11]1[CH3:12]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([Br:9])[n:10][n:11]2[CH3:12])[CH2:13][CH2:14]1 | CN1CCNCC1.Cn1nc(Br)nc1Br | CN1CCN(c2nc(Br)nn2C)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 | 25f33bc88760dab0b15ef207bf05b2bb9c56544162de9cfdb0cab57ce8cae041 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1n[nH]c(N2CCNCC2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[#7;a:5]:1-[C;D1;H3:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:6]-[#7;a:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | 0 | [{"value": 0.0, "product": "CN1CCN(CC1)C2=NC(=NN2C)Br", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A mixture of 3,5-dibromo-1-methyl-1H-1,2,4-triazole (142 mg, 0.59 mmol), 1-methylpiperazine (62.0 mg, 0.62 mmol), tris(dibenzylideneacetone)dipalladium(0) (81 mg, 0.09 mmol), BINAP (110 mg, 0.18 mmol) and sodium tert-butoxide (113 mg, 1.18 mmol) in toluene (8 ml) was stirred at 100 °C for 1.5hrs. LCMS indicated no desi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1nnc[nH]1 | C1C[NH]CC[NH]1.c1nnc[nH]1 | C1C[NH]CC[NH]1.c1nnc[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 | 100 | null | CN1CCNCC1.Cn1nc(Br)nc1Br>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>CN1CCN(c2nc(Br)nn2C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a75ed1ad0e7c4cabb7785476d93cfc86 | Clc1cccnc1Br.NC1CCC1>>Clc1cccnc1NC1CCC1 | C1=CC(=C(N=C1)Br)Cl.C1CC(C1)N>>C1CC(C1)NC2=C(C=CC=N2)Cl | Br[c:7]1[c:2]([Cl:1])[cH:3][cH:4][cH:5][n:6]1.[NH2:8][CH:9]1[CH2:10][CH2:11][CH2:12]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[NH:8][CH:9]1[CH2:10][CH2:11][CH2:12]1 | Clc1cccnc1Br.NC1CCC1 | Clc1cccnc1NC1CCC1 | 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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6])-[C:10] | 25.02 | [{"value": 25.02, "product": "C1CC(C1)NC2=C(C=CC=N2)Cl", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | Pd2(dba)3 (0.014 g, 0.02 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.019 g, 0.03 mmol) and toluene (8 mL) was added to a flask. 2-bromo-3-chloropyridine (0.4 g, 2.08 mmol), cyclobutanamine (0.177 g, 2.49 mmol) and sodium 2-methylpropan-2-olate (0.348 g, 3.62 mmol) was added, the mixture bubbled wi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCC1 | 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 | 115 | null | Clc1cccnc1Br.NC1CCC1>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>Clc1cccnc1NC1CCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-15613520ef9b4d099659a0a3ac545228 | Brc1ccncc1.OC1CCNC1>>OC1CCN(c2ccncc2)C1 | C1=CN=CC=C1Br.C1CNCC1O>>C1CN(CC1O)C2=CC=NC=C2 | Br[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1.[OH:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:12]1>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[CH2:12]1 | Brc1ccncc1.OC1CCNC1 | OC1CCN(c2ccncc2)C1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C | 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] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 4ce7f1716cd0b0bc1bd76f94962fe45a1bd7fe2a7a90867b0ae7b00b6ffc65fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCCC2)ccn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#7;a:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:7]-[C:8]-[C:9]-[C:10]-2):[c:6]:[c:5]:1 | 43.01 | [{"value": 43.01, "product": "C1CN(CC1O)C2=CC=NC=C2", "details": "", "is_desired": true}] | 65 | CELSIUS | null | null | In a 50 ml round bottomed flask THF (1 mL) was added to a mixture of 4-bromopyridine (1 g, 6.33 mmol), pyrrolidin-3-ol (0.662 g, 7.60 mmol),2-(dimethylamino)-2'-(dicyclohexylphosphino)biphenyl (0.249 g, 0.63 mmol) and Pd2(dba)3 (0.580 g, 0.63 mmol). To the slurry lithium bis(trimethylsilyl)amide (13.92 mL, 13.92 mmol)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CCNC1 | C1CC[NH]C1.c1ccncc1 | C1CC[NH]C1.c1ccncc1 | HBr | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.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].C1CCOC1 | 65 | null | Brc1ccncc1.OC1CCNC1>[Li+].C[Si](C)(C)[N-][Si](C)(C)C.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].C1CCOC1>OC1CCN(c2ccncc2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ebc6b887cbeb4bbabe382ad2ba715693 | COC(=O)Cc1cc(Br)ccn1.FC1(F)CNC1>>COC(=O)Cc1cc(N2CC(F)(F)C2)ccn1 | COC(=O)CC1=NC=CC(=C1)Br.C1C(CN1)(F)F.Cl>>COC(=O)CC1=NC=CC(=C1)N2CC(C2)(F)F | Br[c:8]1[cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[n:17][cH:16][cH:15]1.[NH:9]1[CH2:10][C:11]([F:12])([F:13])[CH2:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([N:9]2[CH2:10][C:11]([F:12])([F:13])[CH2:14]2)[cH:15][cH:16][n:17]1 | COC(=O)Cc1cc(Br)ccn1.FC1(F)CNC1 | COC(=O)Cc1cc(N2CC(F)(F)C2)ccn1 | 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] | CN(C)C=O | 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](-[C:6]-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:1.[C:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]2-[C:11]-[C:12]-[C:13]-2):[c:10]:1 | 39.89 | [{"value": 39.89, "product": "COC(=O)CC1=NC=CC(=C1)N2CC(C2)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | palladium acetate (1.561 mg, 6.95 µmol) and BINAP (2.71 mg, 4.35 µmol) were added to methyl 2-(4-bromopyridin-2-yl)acetate (100 mg, 0.43 mmol), 3,3 difluoroazetidine hydrochloride (61.9 mg, 0.48 mmol) and cesium carbonate (425 mg, 1.30 mmol) in DMF (5 mL) at 21°C under nitrogen. The resulting mixture was stirred at 120... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CNC1 | c1ccncc1.C1C[NH]C1 | c1ccncc1.C1C[NH]C1 | 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].CN(C)C=O | 120 | null | COC(=O)Cc1cc(Br)ccn1.FC1(F)CNC1>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].CN(C)C=O>COC(=O)Cc1cc(N2CC(F)(F)C2)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c7d1825ed35e4dffbc57a0b9b8fa9354 | CC(=O)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CCNCC1>>CC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1 | CC(=O)C1=CC=C(C=C1)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(=O)C1=CC=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C | Br[c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:22][cH:21]1.[NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[cH:21]... | CC(=O)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CCNCC1 | CC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | 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:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 52.48 | [{"value": 52.48, "product": "CC(=O)C1=CC=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | In a CEM MW vial, p-Bromoacetophenone (729 ml, 6.03 mmol),tert-Butyl 1-piperazinecarboxylate (1.684 g, 9.04 mmol),racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.375 g, 0.60 mmol),Palladium (II) acetate (0.135 g, 0.60 mmol),Cesium carbonate (3.93 g, 12.06 mmol) was taken in toluene (10 ml).The RM was subjected t... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | 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 | 120 | null | CC(=O)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CCNCC1>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>CC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-91d62f2c93df477a8b3df11f707f23e4 | Cc1cc(C)c(S(=O)(=O)N[C@H](CN)C(C)C)c(C)c1.Fc1ccc(-n2ncc3c(Br)cccc32)cc1>>Cc1cc(C)c(S(=O)(=O)N[C@H](CNc2cccc3c2cnn3-c2ccc(F)cc2)C(C)C)c(C)c1 | C1=CC2=C(C=NN2C3=CC=C(C=C3)F)C(=C1)Br.CC1=CC(=C(C(=C1)C)S(=O)(=O)N[C@H](CN)C(C)C)C>>CC1=CC(=C(C(=C1)C)S(=O)(=O)N[C@H](CNC2=C3C=NN(C3=CC=C2)C4=CC=C(C=C4)F)C(C)C)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([S:7](=[O:8])(=[O:9])[NH:10][C@H:11]([CH2:12][NH2:13])[CH:30]([CH3:31])[CH3:32])[c:33]([CH3:34])[cH:35]1.Br[c:14]1[cH:15][cH:16][cH:17][c:18]2[c:19]1[cH:20][n:21][n:22]2-[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([S:7](=[O:8])(=[O:9]... | Cc1cc(C)c(S(=O)(=O)N[C@H](CN)C(C)C)c(C)c1.Fc1ccc(-n2ncc3c(Br)cccc32)cc1 | Cc1cc(C)c(S(=O)(=O)N[C@H](CNc2cccc3c2cnn3-c2ccc(F)cc2)C(C)C)c(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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 84032078b8d0a58faa6339062f366e91e7af38fbd21ef25dfbdc660a975ebd33 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=S(=O)(NCCNc1cccc2c1cnn2-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[c:7]):[#7;a:8]:[c:9]:[c:10]:2:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[c:7]):[#7;a:8]:[c:9]:[c:10]:2:1 | 11.38 | [{"value": 11.38, "product": "CC1=CC(=C(C(=C1)C)S(=O)(=O)N[C@H](CNC2=C3C=NN(C3=CC=C2)C4=CC=C(C=C4)F)C(C)C)C", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | BINAP (0.432 g, 0.69 mmol) and Pd2(dba)3 (0.24 g, 0.26 mmol) were dissolved in toluene (10 mL) and to this (S)-N-(1-amino-3-methylbutan-2-yl)-2,4,6-trimethylbenzenesulfonamide (0.856 g, 3.01 mmol) and 4-bromo-1-(4-fluorophenyl)-1H-indazole (0.876 g, 3.01 mmol) was added followed by sodium tert-butoxide (0.434 g, 4.51 m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cccc2n[nH]cc12 | c1cccc2n[nH]cc12 | c1ccccc1.c1cccc2n[nH]cc12.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 | Cc1cc(C)c(S(=O)(=O)N[C@H](CN)C(C)C)c(C)c1.Fc1ccc(-n2ncc3c(Br)cccc32)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=... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-805e4c9d19604f5ca8a6f376906a62c5 | CCOC(=O)c1cnc2cc(OC)c(Br)cc2c1Nc1ccc(Cl)cc1Cl.CN1CCNCC1>>CCOC(=O)c1cnc2cc(OC)c(N3CCN(C)CC3)cc2c1Nc1ccc(Cl)cc1Cl | CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OC)Br)NC3=C(C=C(C=C3)Cl)Cl.CN1CCNCC1>>CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OC)N3CCN(CC3)C)NC4=C(C=C(C=C4)Cl)Cl | Br[c:14]1[c:11]([O:12][CH3:13])[cH:10][c:9]2[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:24]([NH:25][c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][c:32]3[Cl:33])[c:23]2[cH:22]1.[NH:15]1[CH2:16][CH2:17][N:18]([CH3:19])[CH2:20][CH2:21]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]([O:12][CH3... | CCOC(=O)c1cnc2cc(OC)c(Br)cc2c1Nc1ccc(Cl)cc1Cl.CN1CCNCC1 | CCOC(=O)c1cnc2cc(OC)c(N3CCN(C)CC3)cc2c1Nc1ccc(Cl)cc1Cl | 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 | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ccnc3ccc(N4CCNCC4)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].[#7:9]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]-[#7:9]-[C:14]-[C:13]-2):[c:2]:[c:3]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OC)N3CCN(CC3)C)NC4=C(C=C(C=C4)Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a solution of ethyl 6-bromo-4-(2,4-dichlorophenylamino)-7-methoxyquinoline-3-carboxylate (694 mg, 1.48 mmol) and 1-methylpiperazine (0.246 mL, 2.21 mmol) in dioxane (10 mL) was added cesium carbonate (962 mg, 2.95 mmol), tris(dibenzylideneacetone)dipalladium(0) (67.6 mg, 0.07 mmol) and rac-2,2'-Bis(diphenylphosphino... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CNCC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[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 | 100 | null | CCOC(=O)c1cnc2cc(OC)c(Br)cc2c1Nc1ccc(Cl)cc1Cl.CN1CCNCC1>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-2949f6d733cb41eb863993e4ce1f0a88 | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Cc1cccnc1Br>>Cc1cccnc1N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1 | CC1=C(N=CC=C1)Br.CC(C)(C)OC(=O)N1CCC[C@H](C1)N>>CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C | [NH2:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21]1.Br[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[NH:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21]1 | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Cc1cccnc1Br | Cc1cccnc1N[C@@H]1CCCN(C(=O)OC(C)(C)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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(N[C@@H]2CCCNC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[#7:7]-[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[#7:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6])-[C:11] | 69.75 | [{"value": 69.75, "product": "CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | Production using the conditions which were shown to work in EN07957-76 2016-03-01 14:20; Pd2(DBA)3 (1.05 g) and BINAP (712 mg mg) was stirred in toluene (75 ml). 14:25; 2-bromo-3-methylpyridine (6.94 g), the amine (9.62 g), and sodium t-butoxide (5.43 g), was added to the mixture. 14:30; Heating at 115 °C. In an at... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]CC1 | 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 | 115 | null | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Cc1cccnc1Br>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>Cc1cccnc1N[C@@H]1CCC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1fab0d514b4b411abf5f6ef0f4a2b24e | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Cc1cccnc1Br>>Cc1cccnc1N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1 | CC1=C(N=CC=C1)Br.CC(C)(C)OC(=O)N1CCC[C@H](C1)N>>CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C | [NH2:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21]1.Br[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[NH:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21]1 | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Cc1cccnc1Br | Cc1cccnc1N[C@@H]1CCCN(C(=O)OC(C)(C)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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(N[C@@H]2CCCNC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[#7:7]-[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[#7:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6])-[C:11] | 82.37 | [{"value": 82.37, "product": "CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | Test reaction using the conditions which were shown to work in EN07957-76 2016-02-26 14:30; Pd2(DBA)3 (14 mg) and BINAP (19 mg) was stirred in toluene (2.5 ml). 14:35; 2-bromo-3-methylpyridine (344 mg), sodium t-butoxide (334 mg), and the amine (526 mg) was added to the mixture. 14:40; Heating at 115 °C. 15:10; 81... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]CC1 | 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 | 115 | null | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Cc1cccnc1Br>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>Cc1cccnc1N[C@@H]1CCC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cf1404eae16044b48089126b4e1896af | CCOC(=O)c1cnc2ccc(Br)cc2c1Nc1ccc(F)cc1F.CN1CCNCC1>>CCOC(=O)c1cnc2ccc(N3CCN(C)CC3)cc2c1Nc1ccc(F)cc1F | CCOC(=O)C1=CN=C2C=CC(=CC2=C1NC3=C(C=C(C=C3)F)F)Br.Cl.CN1CCNCC1>>CCOC(=O)C1=CN=C2C=CC(=CC2=C1NC3=C(C=C(C=C3)F)F)N4CCN(CC4)C | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:22]([NH:23][c:24]3[cH:25][cH:26][c:27]([F:28])[cH:29][c:30]3[F:31])[c:21]2[cH:20]1.[NH:13]1[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:... | CCOC(=O)c1cnc2ccc(Br)cc2c1Nc1ccc(F)cc1F.CN1CCNCC1 | CCOC(=O)c1cnc2ccc(N3CCN(C)CC3)cc2c1Nc1ccc(F)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 | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ccnc3ccc(N4CCNCC4)cc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-2):[c:7]:[c:6]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CN=C2C=CC(=CC2=C1NC3=C(C=C(C=C3)F)F)N4CCN(CC4)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a solution of ethyl 6-bromo-4-(2,4-difluorophenylamino)quinoline-3-carboxylate hydrochloride (505 mg, 1.14 mmol) and 1-methylpiperazine (0.189 mL, 1.71 mmol) in dioxane (10 mL) was added cesium carbonate (1113 mg, 3.41 mmol), tris(dibenzylideneacetone)dipalladium(0) (52.1 mg, 0.06 mmol) and rac-2,2'-Bis(diphenylphos... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CNCC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[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 | 100 | null | CCOC(=O)c1cnc2ccc(Br)cc2c1Nc1ccc(F)cc1F.CN1CCNCC1>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>CCOC(=O)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b6527d32ba054a8395bc5ea7808e53a8 | Brc1cccc2cc[nH]c12.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(c2cccc3cc[nH]c23)CC1 | C1=CC2=C(C(=C1)Br)NC=C2.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2NC=C3 | Br[c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][nH:19][c:20]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:21][CH2:22]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][cH:15][c:16]3[cH:17][cH:18][nH:19][c:20]23)[CH2:21][CH2:22]1 | Brc1cccc2cc[nH]c12.CC(C)(C)OC(=O)N1CCNCC1 | CC(C)(C)OC(=O)N1CCN(c2cccc3cc[nH]c23)CC1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | cec763cd38ef11e89524af229a36bb23c084ddc5f46a24529635d8e630366756 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2[nH]ccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1):[c:4](:[c:5]):[#7;a:6]:[c:7] | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2NC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (75 mg, 0.16 mmol) and palladium (II) acetate (18.08 mg, 0.08 mmol) were dissoved in toluene (2 mL) at ambient temperature. The mixture was degassed and purged with nitrogen and warmed to 50°C for 20 mins. In a separate vessel, were mixed tert-butyl piperazine-1... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | Brc1cccc2cc[nH]c12.CC(C)(C)OC(=O)N1CCNCC1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2cccc3cc[nH]c23)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-636da506499347d7aba99b6e3204f5ba | CC(C)(C)OC(=O)N1CCNCC1.COc1ccccc1Br>>COc1ccccc1N1CCN(C(=O)OC(C)(C)C)CC1 | COC1=CC=CC=C1Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC | [NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.Br[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccccc1Br | COc1ccccc1N1CCN(C(=O)OC(C)(C)C)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 | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 62.37 | [{"value": 62.37, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.059 g, 0.06 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.080 g, 0.13 mmol) were mixed in toluene (10 mL) and degessed at 90 °C for 10 mins. The mixture was then cooled and 1-bromo-2-methoxybenzene (0.400 mL, 3.21 mmol), sodium 2-methylpropan-2-olate (0.493 g, 5.13... | 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 | 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 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccccc1Br>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>COc1ccccc1N1CCN(C(=O)OC(C)(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6e943c9408c04e8290b1b5ad8908a7f2 | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)CCn2ncc(-c3cc(Cl)ncc3F)c2C1>>CC1(C)CCn2ncc(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)c2C1 | CC1(CCN2C(=C(C=N2)C3=CC(=NC=C3F)Cl)C1)C.CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N>>CC1(CCN2C(=C(C=N2)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C1)C | [NH2:13][C:14](=[O:15])[C@H:16]1[CH2:17][CH2:18][CH2:19][C@@H:20]([NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29]1.Cl[c:12]1[cH:11][c:10](-[c:9]2[cH:8][n:7][n:6]3[c:34]2[CH2:35][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5]3)[c:32]([F:33])[cH:31][n:30]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][n:6]2[n:7][cH... | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)CCn2ncc(-c3cc(Cl)ncc3F)c2C1 | CC1(C)CCn2ncc(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)c2C1 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1cc(-c2cnn3c2CCCC3)ccn1)C1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 52.81 | [{"value": 52.81, "product": "CC1(CCN2C(=C(C=N2)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C1)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Tetrakis(triphenylphosphine)palladium(0) (0.496 g, 0.43 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (1.2g, 4.29 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (1.039 g, 4.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.496 g, 0.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccncc1 | c1ccncc1 | c1cc2n(n1)CCCC2.c1ccncc1.C1CCCCC1 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].C1COCCO1 | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)CCn2ncc(-c3cc(Cl)ncc3F)c2C1>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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bdce974c72714a5996ad19d3b75acd9c | COc1cc(F)ccc1-c1nc(Cl)ncc1F.CS(=O)(=O)Cc1cc(N)cc(F)c1>>COc1cc(F)ccc1-c1nc(Nc2cc(F)cc(CS(C)(=O)=O)c2)ncc1F | COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)Cl.CS(=O)(=O)CC1=CC(=CC(=C1)F)N>>COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)NC3=CC(=CC(=C3)CS(=O)(=O)C)F | Cl[c:12]1[n:11][c:10](-[c:9]2[c:3]([O:2][CH3:1])[cH:4][c:5]([F:6])[cH:7][cH:8]2)[c:28]([F:29])[cH:27][n:26]1.[NH2:13][c:14]1[cH:15][c:16]([F:17])[cH:18][c:19]([CH2:20][S:21]([CH3:22])(=[O:23])=[O:24])[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1-[c:10]1[n:11][c:12]([NH:13][c:14]2[cH:15][c:16]([F:17])... | COc1cc(F)ccc1-c1nc(Cl)ncc1F.CS(=O)(=O)Cc1cc(N)cc(F)c1 | COc1cc(F)ccc1-c1nc(Nc2cc(F)cc(CS(C)(=O)=O)c2)ncc1F | 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 | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3ccccc3)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:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 60.61 | [{"value": 60.61, "product": "COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)NC3=CC(=CC(=C3)CS(=O)(=O)C)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (0.12 g, 0.47 mmol), 3-fluoro-5-((methylsulfonyl)methyl)aniline (0.095 g, 0.47 mmol), cesium carbonate (0.609 g, 1.87 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.068 g, 0.12 mmol)and Pd2(dba)3 (0.086 g, 0.09 mmol) were suspended in degasse... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | 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 | 100 | null | COc1cc(F)ccc1-c1nc(Cl)ncc1F.CS(=O)(=O)Cc1cc(N)cc(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.[Pd].[Pd].C1COCCO1>COc1cc(F)ccc1-... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8563d32d81ef4e67b37807469f34e85c | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1>>CC1(C)Cc2c(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)cnn2C1 | CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)Cl)C.CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N>>CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C | [NH2:10][C:11](=[O:12])[C@H:13]1[CH2:14][CH2:15][CH2:16][C@@H:17]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]1.Cl[c:9]1[cH:8][c:7](-[c:6]2[c:5]3[n:33]([n:32][cH:31]2)[CH2:34][C:2]([CH3:1])([CH3:3])[CH2:4]3)[c:29]([F:30])[cH:28][n:27]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[c:6](-[c:7]3[cH:8][c... | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1 | CC1(C)Cc2c(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)cnn2C1 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1cc(-c2cnn3c2CCC3)ccn1)C1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 35.11 | [{"value": 35.11, "product": "CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Tetrakis(triphenylphosphine)palladium(0) (56.5 mg, 0.05 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (130 mg, 0.49 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (119 mg, 0.49 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (56.6 mg, 0.10 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1.c1cc2n(n1)CCC2 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].C1COCCO1 | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1>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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-180ffbd2722940d2bf70ecaf0fc8e2ac | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1>>CC1(C)Cc2c(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)cnn2C1 | CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)Cl)C.CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N>>CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C | [NH2:10][C:11](=[O:12])[C@H:13]1[CH2:14][CH2:15][CH2:16][C@@H:17]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]1.Cl[c:9]1[cH:8][c:7](-[c:6]2[c:5]3[n:33]([n:32][cH:31]2)[CH2:34][C:2]([CH3:1])([CH3:3])[CH2:4]3)[c:29]([F:30])[cH:28][n:27]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[c:6](-[c:7]3[cH:8][c... | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1 | CC1(C)Cc2c(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)cnn2C1 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1cc(-c2cnn3c2CCC3)ccn1)C1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 53.6 | [{"value": 53.6, "product": "CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Tetrakis(triphenylphosphine)palladium(0) (159 mg, 0.14 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (365.4 mg, 1.38 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (333 mg, 1.38 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (Xantphos) (15... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1.c1cc2n(n1)CCC2 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].C1COCCO1 | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1>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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bd4700a79525457dbcfd3c5e1368118f | Brc1ccccc1.c1ccc(C2CCCCN2)cc1>>c1ccc(C2CCCCN2c2ccccc2)cc1 | C1=CC=C(C=C1)Br.C1CCNC(C1)C2=CC=CC=C2>>C1CCN(C(C1)C2=CC=CC=C2)C3=CC=CC=C3 | Br[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][NH:10]2)[cH:17][cH:18]1>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][N:10]2[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1 | Brc1ccccc1.c1ccc(C2CCCCN2)cc1 | c1ccc(C2CCCCN2c2ccccc2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(C2CCCCN2c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[c:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:6]-[C:7](-[c:8])-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:10]-[C:11] | 15.56 | [{"value": 15.56, "product": "C1CCN(C(C1)C2=CC=CC=C2)C3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Caesium carbonate (556 mg, 1.71 mmol) was added to bromobenzene (0.060 mL, 0.57 mmol) and 2-phenylpiperidine (110 mg, 0.68 mmol) in 1,4-dioxane (2 mL). The reaction was degassed and Tris(dibenzylideneacetone)?dipalladium(0) (13.01 mg, 0.01 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (RuPhos... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=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].C1COCCO1 | 100 | null | Brc1ccccc1.c1ccc(C2CCCCN2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=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].C1COCCO1>c1ccc(C2CCCCN2c2ccccc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-87941c7f7d4a47aaba74791eabfbedf7 | CC(C)(C)OC(=O)N1CCNCC1.COc1cc(Br)ccc1OCc1ccccc1>>COc1cc(N2CCNCC2)ccc1OCc1ccccc1 | COC1=C(C=CC(=C1)Br)OCC2=CC=CC=C2.CC(C)(C)OC(=O)N1CCNCC1>>COC1=C(C=CC(=C1)N2CCNCC2)OCC3=CC=CC=C3 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:13][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH... | CC(C)(C)OC(=O)N1CCNCC1.COc1cc(Br)ccc1OCc1ccccc1 | COc1cc(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 | OtherReaction | 1155a782af40ddd9c7c7ab45b40bc8450f26a553a41c0f0d5dfec075d80a69f3 | 4692e9cfac8ca0f49eb5c33838ae1fa5c1a375a44556f0da8885d569da661aa1 | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:6]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]-[NH;D2;+0:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 60.33 | [{"value": 60.33, "product": "COC1=C(C=CC(=C1)N2CCNCC2)OCC3=CC=CC=C3", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | To tert-butyl piperazine-1-carboxylate (0.635 g, 3.41 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.094 g, 0.10 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.085 g, 0.14 mmol) and Sodium tert-butoxide (0.459 g, 4.78 mmol) was added a solution of 1-(benzyloxy)-4-bromo-2-methoxybenzene (1 g, 3.41 mmol) in... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | C1C[NH]CCN1.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 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.COc1cc(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>COc1cc(N2CCNCC2... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-72db1f71b9ee4c528872b1ba0810230a | Brc1ccncc1.Nc1ccccc1>>c1ccc(Nc2ccncc2)cc1 | C1=CN=CC=C1Br.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=CC=NC=C2 | Br[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1.[cH:1]1[cH:2][cH:3][c:4]([NH2:5])[cH:12][cH:13]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][cH:13]1 | Brc1ccncc1.Nc1ccccc1 | c1ccc(Nc2ccncc2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | 24.88 | [{"value": 24.88, "product": "C1=CC=C(C=C1)NC2=CC=NC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | ANILINE (3.94 mL, 43.29 mmol) was added to 4-bromopyridine (5.7 g, 36.08 mmol), PALLADIUM(II) ACETATE (0.162 g, 0.72 mmol), XANTPHOS (1.252 g, 2.16 mmol) and SODIUM TERT-BUTOXIDE (4.85 g, 50.51 mmol) in toluene (280 mL) under nitrogen. The resulting mixture was stirred at 100 °C for 4 hours. The reaction mixture was ev... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | Brc1ccncc1.Nc1ccccc1>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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>c1ccc(Nc2ccncc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b128920e4d7f4cc2b5aeb697ff28a01f | Brc1ccncc1.Nc1ccccc1>>c1ccc(Nc2ccncc2)cc1 | C1=CN=CC=C1Br.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=CC=NC=C2 | Br[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1.[cH:1]1[cH:2][cH:3][c:4]([NH2:5])[cH:12][cH:13]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][cH:13]1 | Brc1ccncc1.Nc1ccccc1 | c1ccc(Nc2ccncc2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | 40.92 | [{"value": 40.92, "product": "C1=CC=C(C=C1)NC2=CC=NC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | ANILINE (1.730 mL, 18.99 mmol) was added to 4-bromopyridine (2.5 g, 15.82 mmol), PALLADIUM(II) ACETATE (0.071 g, 0.32 mmol), XANTPHOS (0.549 g, 0.95 mmol) and SODIUM TERT-BUTOXIDE (2.129 g, 22.15 mmol) in toluene (125 mL) under nitrogen. The resulting mixture was stirred at 100 °C for 4 hours. The reaction mixture was ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | Brc1ccncc1.Nc1ccccc1>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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>c1ccc(Nc2ccncc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3201a37afe8b4b36ad112c88df6755f7 | Brc1ccncc1.Nc1ccccc1>>c1ccc(Nc2ccncc2)cc1 | C1=CN=CC=C1Br.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=CC=NC=C2 | Br[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1.[cH:1]1[cH:2][cH:3][c:4]([NH2:5])[cH:12][cH:13]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][cH:13]1 | Brc1ccncc1.Nc1ccccc1 | c1ccc(Nc2ccncc2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | 20.25 | [{"value": 20.25, "product": "C1=CC=C(C=C1)NC2=CC=NC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | ANILINE (6.85 mL, 75.19 mmol) was added to 4-bromopyridine (9.9 g, 62.66 mmol), PALLADIUM(II) ACETATE (0.281 g, 1.25 mmol), XANTPHOS (2.175 g, 3.76 mmol) and SODIUM TERT-BUTOXIDE (8.43 g, 87.72 mmol) in toluene (500 mL) under nitrogen. The resulting mixture was stirred at 100 °C for 4 hours. The reaction mixture was ev... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | Brc1ccncc1.Nc1ccccc1>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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>c1ccc(Nc2ccncc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1208d74fc7a748139625e9e704ab1724 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)OC(=O)n1ccc2cccc(Br)c21>>CC(C)(C)OC(=O)N1CCN(c2cccc3ccn(C(=O)OC(C)(C)C)c23)CC1 | CC(C)(C)OC(=O)N1C=CC2=C1C(=CC=C2)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2N(C=C3)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:28][CH2:29]1.Br[c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][n:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]12>>[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][cH:1... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)OC(=O)n1ccc2cccc(Br)c21 | CC(C)(C)OC(=O)N1CCN(c2cccc3ccn(C(=O)OC(C)(C)C)c23)CC1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | f8cef21584f7d39f8e4f15fb505737d86121449db74cc5fb2571618d4213e30c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2[nH]ccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8:8]-[C:7](=[O;D1;H0:9])-[#7;a:6](:[c:10]):[c:4](:[c:5]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:15]-[C:16]-[#7:11]-[C:12]-[C:13]-1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2N(C=C3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium (II) acetate (37.9 mg, 0.17 mmol) and 2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (158 mg, 0.34 mmol) were dissolved in toluene (3 mL) and the resulting solution degassed and purged with nitrogen. The mixture was warmed to 50°C for 15 mins. In a separate vessel, were mixed tert-butyl piperazine-... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cccc2cc[nH]c12 | C1C[NH]CC[NH]1.c1cccc2cc[nH]c12 | C1C[NH]CC[NH]1.c1cccc2cc[nH]c12 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)OC(=O)n1ccc2cccc(Br)c21>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2cccc3ccn(C(=O)OC(C)(C)C)c23)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5c1e7b0afe1e4c2ea268d161da8ff7be | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)OC(=O)n1ccc2cccc(Br)c21>>CC(C)(C)OC(=O)N1CCN(c2cccc3ccn(C(=O)OC(C)(C)C)c23)CC1 | CC(C)(C)OC(=O)N1C=CC2=C1C(=CC=C2)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2N(C=C3)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:28][CH2:29]1.Br[c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][n:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]12>>[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][cH:1... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)OC(=O)n1ccc2cccc(Br)c21 | CC(C)(C)OC(=O)N1CCN(c2cccc3ccn(C(=O)OC(C)(C)C)c23)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | f8cef21584f7d39f8e4f15fb505737d86121449db74cc5fb2571618d4213e30c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2[nH]ccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8:8]-[C:7](=[O;D1;H0:9])-[#7;a:6](:[c:10]):[c:4](:[c:5]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:15]-[C:16]-[#7:11]-[C:12]-[C:13]-1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2N(C=C3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | _Trial reaction_ Palladium (II) acetate (7.58 mg, 0.03 mmol) and 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (31.5 mg, 0.07 mmol) were suspended in 1,4-dioxane (1 mL) at ambient temperature. The mixture was degassed and purged with nitrogen and warmed to 50°C for 20 mins. In a separate vessel, were mixed... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cccc2cc[nH]c12 | C1C[NH]CC[NH]1.c1cccc2cc[nH]c12 | C1C[NH]CC[NH]1.c1cccc2cc[nH]c12 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 95 | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)OC(=O)n1ccc2cccc(Br)c21>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CC(C)(C)OC(=O)N1CCN(c2cccc3ccn(C(=O)OC(C)(C)C)c23)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cdacdc2f62e2433897c344ea48603986 | Clc1ccccn1.Nc1ncco1>>c1ccc(Nc2ncco2)nc1 | C1=CC=NC(=C1)Cl.C1=COC(=N1)N>>C1=CC=NC(=C1)NC2=NC=CO2 | Cl[c:4]1[cH:3][cH:2][cH:1][cH:12][n:11]1.[NH2:5][c:6]1[n:7][cH:8][cH:9][o:10]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][o:10]2)[n:11][cH:12]1 | Clc1ccccn1.Nc1ncco1 | c1ccc(Nc2ncco2)nc1 | 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(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1=CC=NC(=C1)NC2=NC=CO2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (4.49 mg, 0.02 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.017 g, 0.03 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Dioxane (1 mL) was added and the resulting mixture was heated to to 50°C for 30 minutes. oxazol-2-amine (0.101 g, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | 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 | Clc1ccccn1.Nc1ncco1>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>c1ccc(Nc2ncco2)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-05c9f5ab86694790884a2465aacb6f95 | Clc1ccccn1.Nc1ncco1>>c1ccc(Nc2ncco2)nc1 | C1=CC=NC(=C1)Cl.C1=COC(=N1)N>>C1=CC=NC(=C1)NC2=NC=CO2 | Cl[c:4]1[cH:3][cH:2][cH:1][cH:12][n:11]1.[NH2:5][c:6]1[n:7][cH:8][cH:9][o:10]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][o:10]2)[n:11][cH:12]1 | Clc1ccccn1.Nc1ncco1 | c1ccc(Nc2ncco2)nc1 | C(=O)([O-])[O-].[K+].[K+] | CC(C)(C)P(C1=CC2=CC=CC=C2N1C3=CC=CC=C3)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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1=CC=NC(=C1)NC2=NC=CO2", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Objective: Comparison of the reactivity of 2-aminooxazole in the coupling with 2-chloropyridine using three different catalyst systems ( previously shown to be the best performers in a 96-well Process Research and Development Screen) To an oven-dried microwave vial was added TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | C(=O)([O-])[O-].[K+].[K+].CC(C)(C)P(C1=CC2=CC=CC=C2N1C3=CC=CC=C3)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].C1COCCO1 | 90 | null | Clc1ccccn1.Nc1ncco1>C(=O)([O-])[O-].[K+].[K+].CC(C)(C)P(C1=CC2=CC=CC=C2N1C3=CC=CC=C3)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].C1COCCO1>c1ccc(Nc2ncco2)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-97b674af3d2f488bb5058b76b82c316b | Clc1ccccn1.Nc1ncco1>>c1ccc(Nc2ncco2)nc1 | C1=CC=NC(=C1)Cl.C1=COC(=N1)N>>C1=CC=NC(=C1)NC2=NC=CO2 | Cl[c:4]1[cH:3][cH:2][cH:1][cH:12][n:11]1.[NH2:5][c:6]1[n:7][cH:8][cH:9][o:10]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][o:10]2)[n:11][cH:12]1 | Clc1ccccn1.Nc1ncco1 | c1ccc(Nc2ncco2)nc1 | C(=O)([O-])[O-].[K+].[K+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)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 | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1=CC=NC(=C1)NC2=NC=CO2", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Objective: Comparison of the reactivity of 2-aminooxazole in the coupling with 2-chloropyridine using three different catalyst systems ( previously shown to be the best performers in a 96-well Process Research and Development Screen) To an oven-dried microwave vial was added TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | C(=O)([O-])[O-].[K+].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)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 | 90 | null | Clc1ccccn1.Nc1ncco1>C(=O)([O-])[O-].[K+].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)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>c1ccc(Nc2ncco2)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8dd14463cf6743e7a0d8b8896c9d7de0 | Brc1cnc2[nH]ccc2c1.C1COCCN1>>c1cc2cc(N3CCOCC3)cnc2[nH]1 | C1=CNC2=NC=C(C=C21)Br.C1COCCN1>>C1COCCN1C2=CN=C3C(=C2)C=CN3 | Br[c:5]1[cH:4][c:3]2[cH:2][cH:1][nH:15][c:14]2[n:13][cH:12]1.[NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>>[cH:1]1[cH:2][c:3]2[cH:4][c:5]([N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)[cH:12][n:13][c:14]2[nH:15]1 | Brc1cnc2[nH]ccc2c1.C1COCCN1 | c1cc2cc(N3CCOCC3)cnc2[nH]1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d71b1fc037ec7d2d0358cee80a2615ac1ca1defe42dafeec5e8bc96b6b2a3f45 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc2cc(N3CCOCC3)cnc2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-2):[c:7]:[c:6]:1 | 83.63 | [{"value": 83.63, "product": "C1COCCN1C2=CN=C3C(=C2)C=CN3", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (9.9 g, 50.25 mmol), morpholine (7.96 mL, 100.49 mmol), sodium 2-methylpropan-2-olate (19.32 g, 200.98 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (1.172 g, 2.51 mmol) in degassed dioxane (200 mL) was added diacetoxypalladium (1.128 g, 5.02 mmol... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1cnc2[nH]ccc2c1.C1COCCN1 | c1cnc2[nH]ccc2c1.C1COCC[NH]1 | c1cnc2[nH]ccc2c1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | Brc1cnc2[nH]ccc2c1.C1COCCN1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>c1cc2cc(N3CCOCC3)cnc2[nH]1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c34fe67f0c724f1db0a5e6644d227638 | Brc1cnc2[nH]ccc2c1.C1COCCN1>>c1cc2cc(N3CCOCC3)cnc2[nH]1 | C1=CNC2=NC=C(C=C21)Br.C1COCCN1>>C1COCCN1C2=CN=C3C(=C2)C=CN3 | Br[c:5]1[cH:4][c:3]2[cH:2][cH:1][nH:15][c:14]2[n:13][cH:12]1.[NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>>[cH:1]1[cH:2][c:3]2[cH:4][c:5]([N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)[cH:12][n:13][c:14]2[nH:15]1 | Brc1cnc2[nH]ccc2c1.C1COCCN1 | c1cc2cc(N3CCOCC3)cnc2[nH]1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d71b1fc037ec7d2d0358cee80a2615ac1ca1defe42dafeec5e8bc96b6b2a3f45 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc2cc(N3CCOCC3)cnc2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-2):[c:7]:[c:6]:1 | 64.63 | [{"value": 64.63, "product": "C1COCCN1C2=CN=C3C(=C2)C=CN3", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (5.1 g, 25.88 mmol), morpholine (4.10 mL, 51.77 mmol), sodium 2-methylpropan-2-olate (9.95 g, 103.54 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (0.604 g, 1.29 mmol) in degassed dioxane (100 mL) was added diacetoxypalladium (0.581 g, 2.59 mmol) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1cnc2[nH]ccc2c1.C1COCCN1 | c1cnc2[nH]ccc2c1.C1COCC[NH]1 | c1cnc2[nH]ccc2c1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | Brc1cnc2[nH]ccc2c1.C1COCCN1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>c1cc2cc(N3CCOCC3)cnc2[nH]1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d96d0e3f2950466bac2ca8525ac77415 | Brc1cnc2[nH]ccc2c1.C1COCCN1>>c1cc2cc(N3CCOCC3)cnc2[nH]1 | C1=CNC2=NC=C(C=C21)Br.C1COCCN1>>C1COCCN1C2=CN=C3C(=C2)C=CN3 | Br[c:5]1[cH:4][c:3]2[cH:2][cH:1][nH:15][c:14]2[n:13][cH:12]1.[NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>>[cH:1]1[cH:2][c:3]2[cH:4][c:5]([N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)[cH:12][n:13][c:14]2[nH:15]1 | Brc1cnc2[nH]ccc2c1.C1COCCN1 | c1cc2cc(N3CCOCC3)cnc2[nH]1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d71b1fc037ec7d2d0358cee80a2615ac1ca1defe42dafeec5e8bc96b6b2a3f45 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc2cc(N3CCOCC3)cnc2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-2):[c:7]:[c:6]:1 | 90.87 | [{"value": 90.87, "product": "C1COCCN1C2=CN=C3C(=C2)C=CN3", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (9.9 g, 50.25 mmol), morpholine (7.96 mL, 100.49 mmol), sodium 2-methylpropan-2-olate (19.32 g, 200.98 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (2.345 g, 5.02 mmol) in degassed dioxane (200 mL) was added diacetoxypalladium (0.564 g, 2.51 mmol... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1cnc2[nH]ccc2c1.C1COCCN1 | c1cnc2[nH]ccc2c1.C1COCC[NH]1 | c1cnc2[nH]ccc2c1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | Brc1cnc2[nH]ccc2c1.C1COCCN1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>c1cc2cc(N3CCOCC3)cnc2[nH]1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fd407bedbf534487940a2a1f79aacfca | CC(C)(C)[Si](C)(C)OCCN.Fc1cc(Br)ccc1OCc1ccccc1>>CC(C)(C)[Si](C)(C)OCCNc1ccc(OCc2ccccc2)c(F)c1 | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.CC(C)(C)[Si](C)(C)OCCN>>CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH2:11].Br[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)[c:24]([F:25])[cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][c... | CC(C)(C)[Si](C)(C)OCCN.Fc1cc(Br)ccc1OCc1ccccc1 | CC(C)(C)[Si](C)(C)OCCNc1ccc(OCc2ccccc2)c(F)c1 | 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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccccc2)cc1 | Br-[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] | 54.2 | [{"value": 54.2, "product": "CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.399 g, 1.78 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.848 g, 1.78 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (5.00 g, 17.79 mmol), 2-(tert- butyldimethylsilyloxy)ethanamine (4.16 g, 17.79 mmol) and cesium carbonate (8.69 g, 26.6... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CC(C)(C)[Si](C)(C)OCCN.Fc1cc(Br)ccc1OCc1ccccc1>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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)[Si](C)(C)OCCNc1ccc(OCc2ccccc2)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c8028b7fd0b24a71a931a3ca28fc4dd0 | CC(C)(C)[Si](C)(C)OCCN.Fc1cc(Br)ccc1OCc1ccccc1>>CC(C)(C)[Si](C)(C)OCCNc1ccc(OCc2ccccc2)c(F)c1 | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.CC(C)(C)[Si](C)(C)OCCN>>CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH2:11].Br[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)[c:24]([F:25])[cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][c... | CC(C)(C)[Si](C)(C)OCCN.Fc1cc(Br)ccc1OCc1ccccc1 | CC(C)(C)[Si](C)(C)OCCNc1ccc(OCc2ccccc2)c(F)c1 | 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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccccc2)cc1 | Br-[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] | 44.07 | [{"value": 44.07, "product": "CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (42.3 mg, 0.19 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (90 mg, 0.19 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (530 mg, 1.89 mmol), 2-(tert- butyldimethylsilyloxy)ethanamine (441 mg, 1.89 mmol) and cesium carbonate (921 mg, 2.83 mmo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CC(C)(C)[Si](C)(C)OCCN.Fc1cc(Br)ccc1OCc1ccccc1>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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)[Si](C)(C)OCCNc1ccc(OCc2ccccc2)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3a62166a30464afb9cbe502b267cbcba | CNc1ccc(F)cc1.COC(=O)c1ccnc(Br)c1>>COC(=O)c1ccnc(N(C)c2ccc(F)cc2)c1 | COC(=O)C1=CC(=NC=C1)Br.CNC1=CC=C(C=C1)F>>CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)C(=O)OC | [NH:10]([CH3:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.Br[c:9]1[n:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8][c:9]([N:10]([CH3:11])[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[cH:19]1 | CNc1ccc(F)cc1.COC(=O)c1ccnc(Br)c1 | COC(=O)c1ccnc(N(C)c2ccc(F)cc2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=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 | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H3:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10](-[C;D1;H3:9])-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)C(=O)OC", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | In a 100 mL round-bottomed flask (t=g) was methyl 2-bromoisonicotinate (.5 g, 2.31 mmol), 4-fluoro-N-methylaniline (0.348 g, 2.78 mmol), and CS2CO3 (1.056 g, 3.24 mmol) in toluene (16 mL) to give a yellow suspension. Pd2dba3 (0.106 g, 0.12 mmol) and biphenyl-2-yldicyclohexylphosphine (0.122 g, 0.35 mmol) were added. Re... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=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 | 105 | null | CNc1ccc(F)cc1.COC(=O)c1ccnc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=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>COC(=O)c1ccnc(N(C)c2ccc(F)cc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8fdcadcf8d694b72a4ad9ff8119e3e79 | CNc1ccc(F)cc1.COC(=O)c1ccnc(Br)c1>>COC(=O)c1ccnc(N(C)c2ccc(F)cc2)c1 | COC(=O)C1=CC(=NC=C1)Br.CNC1=CC=C(C=C1)F>>CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)C(=O)OC | [NH:10]([CH3:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.Br[c:9]1[n:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8][c:9]([N:10]([CH3:11])[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[cH:19]1 | CNc1ccc(F)cc1.COC(=O)c1ccnc(Br)c1 | COC(=O)c1ccnc(N(C)c2ccc(F)cc2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=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 | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H3:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10](-[C;D1;H3:9])-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)C(=O)OC", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | In a 100 mL round-bottomed flask (t=g) was biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol), methyl 2-bromoisonicotinate (.1 g, 0.46 mmol), and 4-fluoro-N-methylaniline (0.070 g, 0.56 mmol) in toluene (3 mL) to give a purple suspension. Pd2dba3 (0.021 g, 0.02 mmol) and CS2CO3 (0.211 g, 0.65 mmol) were added. Fla... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=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 | 85 | null | CNc1ccc(F)cc1.COC(=O)c1ccnc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=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>COC(=O)c1ccnc(N(C)c2ccc(F)cc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1f9578b402a0413a8d3c28c86e02d21e | COc1nc(N)ncc1Br.FC(F)(F)c1cccc(I)c1>>COc1nc(Nc2cccc(C(F)(F)F)c2)ncc1Br | C1=CC(=CC(=C1)I)C(F)(F)F.COC1=NC(=NC=C1Br)N>>COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:17][cH:18][c:19]1[Br:20].I[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[n:17][cH:18][c:19]1[Br:20] | COc1nc(N)ncc1Br.FC(F)(F)c1cccc(I)c1 | COc1nc(Nc2cccc(C(F)(F)F)c2)ncc1Br | 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] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | I-[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] | 43.23 | [{"value": 43.23, "product": "COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | repeat of _EN06995-58\Reaction_ but using Xantphos **_Aim:-_ prepare target for further use.** 1-iodo-3-(trifluoromethyl)benzene (0.171 ml, 1.19 mmol), 5-bromo-4-methoxypyrimidin-2-amine (0.202 g, 0.99 mmol), PALLADIUM(II) ACETATE (0.011 g, 0.05 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) - Xantp... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1cncnc1.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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 90 | null | COc1nc(N)ncc1Br.FC(F)(F)c1cccc(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].CC1=CC=CC=C1>COc1nc(Nc2cccc(C(F)(F)F)c2)ncc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-81f0402c864a4618afac454715899838 | COC[C@@H]1Cn2cc(-c3nc(Cl)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)c1>>COc1cc(N(CC(C)C)c2cc(C(F)(F)F)ccc2F)cnc1C(=O)[C@H]1C[C@@H]1C(=O)O | CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)Cl.CN1C(=CC=N1)N>>CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F | Clc1n[cH:9][c:8]([CH3:10])[c:24](-[c:5]2n[c:27]3[n:23]([cH:22]2)[CH2:28][C@@H:29]([CH2:30][O:2][CH3:1])[N:6]([CH2:7][c:11]2[cH:12][c:13]([F:16])[c:14]([F:15])[cH:19][cH:20]2)[C:25]3=[O:26])n1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[c:11]2[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH... | COC[C@@H]1Cn2cc(-c3nc(Cl)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)c1 | COc1cc(N(CC(C)C)c2cc(C(F)(F)F)ccc2F)cnc1C(=O)[C@H]1C[C@@H]1C(=O)O | 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] | null | Miscellaneous | OtherReaction | 70b8ff50e3b3494ab0c85f0f2590f38cacc8e5964e2df376ed3f4f651f736bf1 | 0bc23af1f7448f02014172026989c4086c48f0f7b80601908822f169c03f6e16 | O=C(c1ccc(Nc2ccccc2)cn1)C1CC1 | Cl-c1:n:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C;D1;H3:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[c:6]:[n;H0;D3;+0:7]3:[c;H0;D3;+0:8](:n:2)-[C;H0;D3;+0:9](=[O;D1;H0:10])-[N;H0;D3;+0:11](-[CH2;D2;+0:12]-[c;H0;D3;+0:13]2:[c:14]:[c;H0;D3;+0:15](-[F;H0;D1;+0:16]):[c;H0;D3;+0:17](-[F;D1;H0:18]):[cH;D2;+0:19]:[cH;D2;+0:20]:2)-[C@H;D3;+0:21... | 15.7 | [{"value": 15.7, "product": "CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | 18-mar-2014 17:15:52 +0100, blandar allt, add toluen, N2 flushar - rör 110 gC/ön/N2. Nästa em kl 16, fått svalna - LCMS ser bra ut, 17:49:27 - nu hydrolys/rt, klart efter 90 min ca, slår på 600 uL HoAc, evap. Till SSL, 24-mar-2014 190 mg åter från SSL. ( 1 g CBA prekond MeOH, löser i några ml ACN, eluerar mha 2.5 över... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Tertiary amide | Trifluoro group.Aromatic halide.Carboxylic acid.Ketone.Ether.Tertiary amine | c1cncnc1.c1cn2c(n1)C[NH]CC2.c1ccccc1 | c1ccncc1.c1ccccc1.C1CC1 | c1ccncc1.c1ccccc1.C1CC1 | null | 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] | 110 | null | COC[C@@H]1Cn2cc(-c3nc(Cl)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)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]>COc1cc(N(CC(C)C)c2cc(C(F)(F)F)ccc2F)cnc1C(=O)[C@H]1C[C@@H]1C(=O)O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-77fa1d8a9ea647299df5929297f3aa17 | CC(C)CNc1cc(C(F)(F)F)ccc1F.CCOC(=O)C1CC1C(=O)c1ncc(Br)cc1OC>>COc1cc(N(CC(C)C)c2cc(C(F)(F)F)ccc2F)cnc1C(=O)[C@H]1C[C@@H]1C(=O)O | CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)Br)OC.CC(C)CNC1=C(C=CC(=C1)C(F)(F)F)F>>CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F | [NH:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][c:20]1[F:21].CC[O:32][C:30]([CH:29]1[CH:27]([C:25]([c:24]2[c:3]([O:2][CH3:1])[cH:4][c:5](Br)[cH:22][n:23]2)=[O:26])[CH2:28]1)=[O:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[c:11]2[cH:12][c... | CC(C)CNc1cc(C(F)(F)F)ccc1F.CCOC(=O)C1CC1C(=O)c1ncc(Br)cc1OC | COc1cc(N(CC(C)C)c2cc(C(F)(F)F)ccc2F)cnc1C(=O)[C@H]1C[C@@H]1C(=O)O | 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 | OtherReaction | 1d1c315fa1cb429eb23e356970986facda2ac37dffd51d67ef8eba0d9b8f3f55 | 154ad2504fb7aaca0f52c4b8eebdfca329f4106b95adc3c71ff059886f074b58 | O=C(c1ccc(Nc2ccccc2)cn1)C1CC1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:[c:8]:1.C-C-[O;H0;D2;+0:9]-[C:10](-[C:11])=[O;D1;H0:12].[C:13]-[C:14]-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:11]-[C:10](=[O;D1;H0:12])-[OH;D1;+0:9].[C:13]-[C:14]-[N;H0;D3;+0:15](-[c:16](:[c:17]):[c:18])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5]=[O;D1... | 29.09 | [{"value": 29.09, "product": "CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | (allt satsas i Toluen, N2 bubblar) start 09-jun-2014 19:51:32 +0200. LCMS-1 1600 nästa em ser bra ut, hittar inga SM, får svalna - bryter. Späder med 30 ml etoac, filtrerar genom SiO plugg, evap. evap två gånger ur 30 ml THF, LCMS-2 visar P 10-jun-2014 19:15:25 +0200 löser i 20 ml THF, 10 ml MeOH, adderar LiOH(758 mg... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Ester.Secondary amine | Carboxylic acid.Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.C1CC1 | 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 | 110 | null | CC(C)CNc1cc(C(F)(F)F)ccc1F.CCOC(=O)C1CC1C(=O)c1ncc(Br)cc1OC>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>COc1cc(N(CC(C)C)c2cc(C(F)(F)F)ccc2F)cnc1C(=O)[C@H]1C[C@@H]1C(=O)O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2d0a333d9cfc43c6a6709471b22f0443 | COC[C@@H]1Cn2cc(-c3nc(Cl)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)c1.Cn1nccc1N>>COC[C@@H]1Cn2cc(-c3nc(Nc4ccnn4C)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)c1 | CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)Cl.CN1C(=CC=N1)N>>CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)NC5=CC=NN5C | Cl[c:11]1[n:10][c:9](-[c:8]2[cH:7][n:6]3[c:24]([n:23]2)[C:25](=[O:26])[N:27]([CH2:28][c:29]2[cH:30][cH:31][c:32]([F:33])[c:34]([F:35])[cH:36]2)[C@H:4]([CH2:3][O:2][CH3:1])[CH2:5]3)[c:21]([CH3:22])[cH:20][n:19]1.[NH2:12][c:13]1[cH:14][cH:15][n:16][n:17]1[CH3:18]>>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:5][n:6]2[cH:7][c:8](-[c:... | COC[C@@H]1Cn2cc(-c3nc(Cl)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)c1.Cn1nccc1N | COC[C@@H]1Cn2cc(-c3nc(Nc4ccnn4C)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | 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] | CC1CCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1c2nc(-c3ccnc(Nc4ccn[nH]4)n3)cn2CCN1Cc1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a: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]):[#7;a:4]:[c:5] | 55.03 | [{"value": 55.03, "product": "CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)NC5=CC=NN5C", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | 2016-05-18 **time temp comment** 1 14:20 21 (S)-2-(2-chloro-5-methylpyrimidin-4-yl)-7-(3,4-difluorobenzyl)-6-(methoxymethyl)-6,7-dihydroimidazo[1,2-a]pyrazin-8(5H)-one (2.2 g, 5.07 mmol), 1-methyl-1H-pyrazol-5-amine (0.754 g, 7.61 mmol) and cesium carbonate (3.30 g, 10.14 mmol) was charged to a 100mL reactor. 2-met... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cn2c(n1)C[NH]CC2.c1cncnc1.c1cc[nH]n1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].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].CC1CCCO1 | 80 | null | COC[C@@H]1Cn2cc(-c3nc(Cl)ncc3C)nc2C(=O)N1Cc1ccc(F)c(F)c1.Cn1nccc1N>C(=O)([O-])[O-].[Cs+].[Cs+].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].CC1CCCO1>COC[C@@H]1Cn2cc(-c3nc(Nc4ccnn4C)ncc3C)n... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f95171c2975240019dea4c87294370ec | NCCC(N)=O.O=C(O)c1ccc(Br)cc1>>NC(=O)CCNc1ccc(C(=O)O)cc1 | C1=CC(=CC=C1C(=O)O)Br.C(CN)C(=O)N.Cl>>C1=CC(=CC=C1C(=O)O)NCCC(=O)N | [NH2:1][C:2](=[O:3])[CH2:4][CH2:5][NH2:6].Br[c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15]1>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15]1 | NCCC(N)=O.O=C(O)c1ccc(Br)cc1 | NC(=O)CCNc1ccc(C(=O)O)cc1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | C1CCOC1 | 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].[N;D1;H2:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[NH2;D1;+0:11]>>[N;D1;H2:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1=CC(=CC=C1C(=O)O)NCCC(=O)N", "details": "", "is_desired": true}] | 50 | CELSIUS | null | null | Palladium (II) acetate (0.011 g, 0.05 mmol) was added to(R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (0.027 g, 0.05 mmol) in THF (1 mL) in a reaction vessel evacuated and purged with nitrogen. The resulting catalyst mixture was stirred and under nitrogen at 50 °C for 30 minutes. 04-Dec-20... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].C1CCOC1 | 50 | null | NCCC(N)=O.O=C(O)c1ccc(Br)cc1>[Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].C1CCOC1>NC(=O)CCNc1ccc(C(=O)O)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-eba583eb36cf40e597f1d8a3b26c7756 | Clc1cc(Br)c2nccn2c1.Nc1ccc(N2CCOCC2)cn1>>Clc1cc(Nc2ccc(N3CCOCC3)cn2)c2nccn2c1 | C1=CN2C=C(C=C(C2=N1)Br)Cl.C1COCCN1C2=CN=C(C=C2)N>>C1COCCN1C2=CN=C(C=C2)NC3=CC(=CN4C3=NC=C4)Cl | Br[c:4]1[cH:3][c:2]([Cl:1])[cH:23][n:22]2[c:18]1[n:19][cH:20][cH:21]2.[NH2:5][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[cH:16][n:17]1>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[cH:16][n:17]2)[c:18]2[n:19][cH:20][cH:21][n:22]2[cH:23... | Clc1cc(Br)c2nccn2c1.Nc1ccc(N2CCOCC2)cn1 | Clc1cc(Nc2ccc(N3CCOCC3)cn2)c2nccn2c1 | 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) | f626b1d4a6dd63a78117b5d59f65d7bde0ec8313f69d2f89b102dedacea88c4e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc(N3CCOCC3)cn2)c2nccn2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[#7;a:13]:[c:14]>>[c:14]:[#7;a:13]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:12] | 65.27 | [{"value": 65.27, "product": "C1COCCN1C2=CN=C(C=C2)NC3=CC(=CN4C3=NC=C4)Cl", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | A mixture of 8-bromo-6-chloroimidazo[1,2-a]pyridine, HCl (600mg, 2.24 mmol), 5-morpholinopyridin-2-amine (482 mg, 2.69 mmol), BINAP (279 mg, 0.45 mmol), cesium carbonate (1824 mg, 5.60 mmol) in Toluene (12 mL) was sparged with nitrogen while stirring for 10 minutes. palladium(II) acetate (87 mg, 0.39 mmol) was then add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccncc1.C1COCC[NH]1.c1ccn2ccnc2c1 | 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 | 105 | null | Clc1cc(Br)c2nccn2c1.Nc1ccc(N2CCOCC2)cn1>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>Clc1cc(Nc2ccc(N3CCOCC3)cn2)c2nccn2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-945adafe269741f9bc504b4e9b38a0a3 | Clc1cccnc1Br.N[C@@H]1CCCNC1=O>>O=C1NCCC[C@H]1Nc1ncccc1Cl | C1=CC(=C(N=C1)Br)Cl.C1C[C@H](C(=O)NC1)N>>C1C[C@H](C(=O)NC1)NC2=C(C=CC=N2)Cl | Br[c:9]1[n:10][cH:11][cH:12][cH:13][c:14]1[Cl:15].[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH2:8]>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH:8][c:9]1[n:10][cH:11][cH:12][cH:13][c:14]1[Cl:15] | Clc1cccnc1Br.N[C@@H]1CCCNC1=O | O=C1NCCC[C@H]1Nc1ncccc1Cl | 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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCC[C@H]1Nc1ccccn1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6])-[C:13] | 2 | [{"value": 2.0, "product": "C1C[C@H](C(=O)NC1)NC2=C(C=CC=N2)Cl", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | In a 5 ml MW vial, Pd2((dba)3 (7.23 mg, 7.90 µmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (9.71 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (174 mg, 1.81 mmol), (R)-3-aminopiperidin-2-one (119 mg, 1.04 mmol) and 2-bromo-3-chloropyridine (200 mg, 1.04 mmol) mixed in toluene (2 mL) to give a brown sus... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | C1CCNCC1.c1ccncc1 | 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 | 115 | null | Clc1cccnc1Br.N[C@@H]1CCCNC1=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].CC1=CC=CC=C1>O=C1NCCC[C@H]1Nc1ncccc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-31042a5d8fe24c18a416eee8a6a124c6 | Clc1ccnc(Nc2ccccc2)c1.NCc1c(F)cccc1F>>Fc1cccc(F)c1CNc1ccnc(Nc2ccccc2)c1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC(=C(C(=C1)F)CN)F>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=C(C=CC=C3F)F | Cl[c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH2:10]>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH:10][c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1c(F)cccc1F | Fc1cccc(F)c1CNc1ccnc(Nc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 61.13 | [{"value": 61.13, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=C(C=CC=C3F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (2,6-difluorophenyl)methanamine (77 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHO... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1c(F)cccc1F>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Fc1cccc(F)c1CNc1ccnc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7d0087e63ad44356ba79974b84233090 | Clc1ccnc(Nc2ccccc2)c1.NCc1c(F)cccc1F>>Fc1cccc(F)c1CNc1ccnc(Nc2ccccc2)c1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC(=C(C(=C1)F)CN)F>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=C(C=CC=C3F)F | Cl[c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH2:10]>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH:10][c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1c(F)cccc1F | Fc1cccc(F)c1CNc1ccnc(Nc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 21.04 | [{"value": 21.04, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=C(C=CC=C3F)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol), (2,6-difluorophenyl)methanamine (91 mg, 0.64 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol),sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were suspended in DME (2... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC | 150 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1c(F)cccc1F>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>Fc1cccc(F)c1CNc1ccnc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0d9db0bff06f4d53bf85fef23e44393c | CN1Cc2ccc(Cl)nc2O[C@@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)O[C@@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@@H](O4)C5=CC=CC=C5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O... | CN1Cc2ccc(Cl)nc2O[C@@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)O[C@@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@H]2CNCc3ccc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | 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]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 27.89 | [{"value": 27.89, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@@H](O4)C5=CC=CC=C5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.213 g, 0.89 mmol), Palladium(II) acetate (0.017 g, 0.07 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.026 g, 0.07 mmol) and Cesium carbonate (0.722 g, 2.22 mmol) were put in a 20 mL microwave vial and sealed. The vial was flushed with argon. (S)-8-chloro-4-methyl-2-phenyl... | 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 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2O[C@@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)O[C@@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c1f0d60afc5d442f82c1963456675035 | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>CN(C)C(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:22]2[o:23][c:24]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[cH:31][c:32](=[O:33])[c:34]2[cH:35]1.Br[c:14]1[cH:15][c:16]([F:17])[cH:18][c:19]([F:20])[cH:21]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | CN(C)C(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | 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.CC1(C2=C(C(=CC=C2)[PH+](C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5[PH+](C6=CC=CC=C6)C7=CC=CC=C7)C.C1=[C-]C=C(C=C1F)F.Br[Pd+] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 33.8 | [{"value": 33.8, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Pd complexe (2.96 mg, 3.37 µmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (25 mg, 0.07 mmol), 1-bromo-3,5-difluorobenzene (8.53 µl, 0.07 mmol) and cesium carbonate (32.9 mg, 0.10 mmol) dissolved in 1,4-dioxane (0.5 ml) under argon. The resulting sus... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.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.CC1(C2=C(C(=CC=C2)[PH+](C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5[PH+](C6=CC=CC=C6)C7=CC=CC=C7)C.C1=[C-]C=C(C=C1F)F.Br[Pd+].C1COCCO1 | 80 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(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.CC1(C2=C(C(=CC=C2)[PH+](C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5[PH+](C6=CC=CC=C6)C7=CC=CC=C7)C.C1=[C-]C=C(C=C1F)F.Br[Pd+].C1COCCO1>CN(C)C(=O)c1c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-18a5ade19723420ab980b1bccfb56a9b | CN1CCNCC1.Cc1ccc(-c2ncc[nH]2)cc1NC(=O)c1ccc(OCc2ncccc2Br)cc1>>Cc1ccc(-c2ncc[nH]2)cc1NC(=O)c1ccc(OCc2ncccc2N2CCN(C)CC2)cc1 | CC1=C(C=C(C=C1)C2=NC=CN2)NC(=O)C3=CC=C(C=C3)OCC4=C(C=CC=N4)Br.CN1CCNCC1>>CC1=C(C=C(C=C1)C2=NC=CN2)NC(=O)C3=CC=C(C=C3)OCC4=C(C=CC=N4)N5CCN(CC5)C | [NH:28]1[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]1.Br[c:27]1[c:22]([CH2:21][O:20][c:19]2[cH:18][cH:17][c:16]([C:14]([NH:13][c:12]3[c:2]([CH3:1])[cH:3][cH:4][c:5](-[c:6]4[n:7][cH:8][cH:9][nH:10]4)[cH:11]3)=[O:15])[cH:36][cH:35]2)[n:23][cH:24][cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9]... | CN1CCNCC1.Cc1ccc(-c2ncc[nH]2)cc1NC(=O)c1ccc(OCc2ncccc2Br)cc1 | Cc1ccc(-c2ncc[nH]2)cc1NC(=O)c1ccc(OCc2ncccc2N2CCN(C)CC2)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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(Nc1cccc(-c2ncc[nH]2)c1)c1ccc(OCc2ncccc2N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | 0 | [{"value": 0.0, "product": "CC1=C(C=C(C=C1)C2=NC=CN2)NC(=O)C3=CC=C(C=C3)OCC4=C(C=CC=N4)N5CCN(CC5)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A mixture of N-(5-(1H-imidazol-2-yl)-2-methylphenyl)-4-((3-bromopyridin-2-yl)methoxy)benzamide (50 mg, 0.11 mmol), 1-methylpiperazine (32.4 mg, 0.32 mmol), Pd2(dba)3 (19.76 mg, 0.02 mmol) and BINAP (26.9 mg, 0.04 mmol), CS2CO3 (70.3 mg, 0.22 mmol) in DMA (5 mL) was stirred at 100 °C for overnight. LCMS didn't mornitor ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccncc1 | c1ccncc1.C1C[NH]CC[NH]1 | c1ccccc1.c1c[nH]cn1.c1ccccc1.c1ccncc1.C1C[NH]CC[NH]1 | 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].CC(=O)N(C)C | 100 | null | CN1CCNCC1.Cc1ccc(-c2ncc[nH]2)cc1NC(=O)c1ccc(OCc2ncccc2Br)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].CC(=O)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c9fc8ca9766b49dfbbd86d67f996e21e | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.Fc1cnc(Cl)cc1-c1cnn2c1CCCC2>>CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(=O)Nc2cc(-c3cnn4c3CCCC4)c(F)cn2)C1 | C1CCN2C(=C(C=N2)C3=CC(=NC=C3F)Cl)C1.CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N>>CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCN4N=C3)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[NH2:16])[CH2:33]1.Cl[c:17]1[cH:18][c:19](-[c:20]2[cH:21][n:22][n:23]3[c:24]2[CH2:25][CH2:26][CH2:27][CH2:28]3)[c:29]([F:30])[cH:31][n:32]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:... | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.Fc1cnc(Cl)cc1-c1cnn2c1CCCC2 | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(=O)Nc2cc(-c3cnn4c3CCCC4)c(F)cn2)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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1cc(-c2cnn3c2CCCC3)ccn1)C1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 37.41 | [{"value": 37.41, "product": "CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCN4N=C3)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Tetrakis(triphenylphosphine)palladium(0) (0.092 g, 0.08 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (0.200 g, 0.79 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (0.231 g, 0.95 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.092 g, 0.16 mmol) a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccncc1 | c1ccncc1 | C1CCCCC1.c1ccncc1.c1cc2n(n1)CCCC2 | 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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].C1COCCO1 | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1.Fc1cnc(Cl)cc1-c1cnn2c1CCCC2>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)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e6335b06fa23489ab5143a6fe79c709a | CC(N)c1ncc(F)cn1.Cn1cnc(Nc2nc(Cl)nc3c2ccn3C2CC2)c1>>CC(Nc1nc(Nc2cn(C)cn2)c2ccn(C3CC3)c2n1)c1ncc(F)cn1 | CN1C=C(N=C1)NC2=C3C=CN(C3=NC(=N2)Cl)C4CC4.CC(C1=NC=C(C=N1)F)N.Cl>>CC(C1=NC=C(C=N1)F)NC2=NC(=C3C=CN(C3=N2)C4CC4)NC5=CN(C=N5)C | [CH3:1][CH:2]([NH2:3])[c:23]1[n:24][cH:25][c:26]([F:27])[cH:28][n:29]1.Cl[c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][n:10]([CH3:11])[cH:12][n:13]2)[c:14]2[cH:15][cH:16][n:17]([CH:18]3[CH2:19][CH2:20]3)[c:21]2[n:22]1>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][n:10]([CH3:11])[cH:12][n:13]2)[c:14]2[cH:15][cH:16][n:1... | CC(N)c1ncc(F)cn1.Cn1cnc(Nc2nc(Cl)nc3c2ccn3C2CC2)c1 | CC(Nc1nc(Nc2cn(C)cn2)c2ccn(C3CC3)c2n1)c1ncc(F)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 7d8cc6c05eda9dfa6bdabe6a29061e2976ad8c7049d801bee87af917df08c113 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc(CNc2nc(Nc3c[nH]cn3)c3ccn(C4CC4)c3n2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9].[#7;a:10]:[c:11](-[C:12](-[C;D1;H3:13])-[NH2;D1;+0:14]):[#7;a:15]>>[#7;a:10]:[c:11](-[C:12](-[C;D1;H3:13])-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9]):[#7;a:15] | 37.23 | [{"value": 37.23, "product": "CC(C1=NC=C(C=N1)F)NC2=NC(=C3C=CN(C3=N2)C4CC4)NC5=CN(C=N5)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | A mixture of 1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (252 mg, 1.42 mmol), 2-chloro-7-cyclopropyl-N-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (205 mg, 0.71 mmol), palladium(II) acetate (15.94 mg, 0.07 mmol) and palladium(II) acetate (15.94 mg, 0.07 mmol) (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | c1c[nH]cn1.c1ncc2cc[nH]c2n1.C1CC1.c1cncnc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | CC(N)c1ncc(F)cn1.Cn1cnc(Nc2nc(Cl)nc3c2ccn3C2CC2)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CC(Nc1nc(Nc2cn(C)cn2)c2ccn(C3CC3)c2n1)c1ncc(F)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3d49493a2a1a42b2b80747d57867d066 | COc1cccc(CN)c1.Clc1ccnc(Nc2ccccc2)c1>>COc1cccc(CNc2ccnc(Nc3ccccc3)c2)c1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.COC1=CC=CC(=C1)CN>>COC1=CC=CC(=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:23]1.Cl[c:10]1[cH:11][cH:12][n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22]2)[cH:23]1 | COc1cccc(CN)c1.Clc1ccnc(Nc2ccccc2)c1 | COc1cccc(CNc2ccnc(Nc3ccccc3)c2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 53.61 | [{"value": 53.61, "product": "COC1=CC=CC(=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (3-methoxyphenyl)methanamine (73.7 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | COc1cccc(CN)c1.Clc1ccnc(Nc2ccccc2)c1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>COc1cccc(CNc2ccnc(Nc3ccccc3)c2)c1 |
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