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-1cf3f1a64d944eabb1ba184483ae76fd | Brc1cncc(Br)c1.CN1CCNCC1>>CN1CCN(c2cncc(Br)c2)CC1 | C1=C(C=NC=C1Br)Br.CN1CCNCC1>>CN1CCN(CC1)C2=CC(=CN=C2)Br | Br[c:6]1[cH:7][n:8][cH:9][c:10]([Br:11])[cH:12]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:13][CH2:14]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][n:8][cH:9][c:10]([Br:11])[cH:12]2)[CH2:13][CH2:14]1 | Brc1cncc(Br)c1.CN1CCNCC1 | CN1CCN(c2cncc(Br)c2)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 | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-[C:11]-[C:12]-1 | 21.27 | [{"value": 21.27, "product": "CN1CCN(CC1)C2=CC(=CN=C2)Br", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Trial # 3: 3,5-dibromopyridine (1000 mg, 4.22 mmol), 1-methylpiperazine (423 mg, 4.22 mmol), Pd2(dba)3 (387 mg, 0.42 mmol), XANTPHOS (366 mg, 0.63 mmol), SODIUM TERT-BUTOXIDE (609 mg, 6.33 mmol), PhCH3 (10 mL) as added to a 10 mL microwave vial. This was degassed and refilled with N2 and then heated at 140 °C in micro... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1C[NH]CCN1 | 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 | 140 | null | Brc1cncc(Br)c1.CN1CCNCC1>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>CN1CCN(c2cncc(Br)c2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-37aa4a46f5494844887cf9e7ccaf1b0d | CC(C)(C)OC(=O)N1CCNCC1.Clc1cccs1>>CC(C)(C)OC(=O)N1CCN(c2cccs2)CC1 | C1=CSC(=C1)Cl.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CS2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:17][CH2:18]1.Cl[c:12]1[cH:13][cH:14][cH:15][s:16]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][s:16]2)[CH2:17][CH2:18]1 | CC(C)(C)OC(=O)N1CCNCC1.Clc1cccs1 | CC(C)(C)OC(=O)N1CCN(c2cccs2)CC1 | CCN(CC)CC | 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.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | f0e088788c796fa9f300a74179578f507177fccd6f87c800b796738a1c1bf403 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1csc(N2CCNCC2)c1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#16;a:2]1:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1 | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CS2", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | To a mixture of 2-chlorothiophene (0.248 mL, 2.68 mmol), tert-butyl piperazine-1-carboxylate (500 mg, 2.68 mmol), and TEA (1.123 mL, 8.05 mmol) in DMF (4 mL) was added Pd(Ph3P)4 (57.8 mg, .05 mmol). The reaction was allowed to heat at 95 °C for overnight. LCMS and TLC showed the starting material peak as well as the tr... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccsc1 | C1C[NH]CC[NH]1.c1ccsc1 | C1C[NH]CC[NH]1.c1ccsc1 | HCl | CCN(CC)CC.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.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].CN(C)C=O | 95 | null | CC(C)(C)OC(=O)N1CCNCC1.Clc1cccs1>CCN(CC)CC.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.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].CN(C)C=O>CC(C)(C)OC(=O)N1CCN(c2cccs2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c7ac817750064edba47d3c6c786a7b69 | NC(=O)c1ccc(Cl)nc1.NCc1ccccc1C(F)(F)F>>NC(=O)c1ccc(NCc2ccccc2C(F)(F)F)nc1 | C1=CC(=NC=C1C(=O)N)Cl.C1=CC=C(C(=C1)CN)C(F)(F)F>>C1=CC=C(C(=C1)CNC2=NC=C(C=C2)C(=O)N)C(F)(F)F | Cl[c:7]1[cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:21][n:20]1.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16]([F:17])([F:18])[F:19]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]([F:17])([F:18])[F:19])[n:20][cH:21]1 | NC(=O)c1ccc(Cl)nc1.NCc1ccccc1C(F)(F)F | NC(=O)c1ccc(NCc2ccccc2C(F)(F)F)nc1 | 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] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 1.45 | [{"value": 1.45, "product": "C1=CC=C(C(=C1)CNC2=NC=C(C=C2)C(=O)N)C(F)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.021 g, 0.03 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (2-(trifluoromethyl)phenyl)methanamine (0.095 mL, 0.68 mmol). The r... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].COCCOC | 120 | null | NC(=O)c1ccc(Cl)nc1.NCc1ccccc1C(F)(F)F>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].COCCOC>NC(=O)c1ccc(NCc2ccccc2C(F)(F)F)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-058876800e774f05bf1b52bd00238231 | NC(=O)c1ccc(Cl)nc1.NCc1cccc(C(F)(F)F)c1>>NC(=O)c1ccc(NCc2cccc(C(F)(F)F)c2)nc1 | C1=CC(=NC=C1C(=O)N)Cl.C1=CC(=CC(=C1)C(F)(F)F)CN>>C1=CC(=CC(=C1)C(F)(F)F)CNC2=NC=C(C=C2)C(=O)N | Cl[c:7]1[cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:21][n:20]1.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]2)[n:20][cH:21]1 | NC(=O)c1ccc(Cl)nc1.NCc1cccc(C(F)(F)F)c1 | NC(=O)c1ccc(NCc2cccc(C(F)(F)F)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.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1=CC(=CC(=C1)C(F)(F)F)CNC2=NC=C(C=C2)C(=O)N", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.020 g, 0.03 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (3-(trifluoromethyl)phenyl)methanamine (0.049 mL, 0.3... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | 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.CC(=O)O.CC(=O)O.[Pd].COCCOC | 120 | null | NC(=O)c1ccc(Cl)nc1.NCc1cccc(C(F)(F)F)c1>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].COCCOC>NC(=O)c1ccc(NCc2cccc(C(F)(F)F)c2)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-92bacb0740454b4398d7f3969518ce26 | NC(=O)c1ccc(Cl)nc1.NCc1ccc(C(F)(F)F)cc1>>NC(=O)c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1 | C1=CC(=NC=C1C(=O)N)Cl.C1=CC(=CC=C1CN)C(F)(F)F>>C1=CC(=CC=C1CNC2=NC=C(C=C2)C(=O)N)C(F)(F)F | Cl[c:7]1[cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:21][n:20]1.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[n:20][cH:21]1 | NC(=O)c1ccc(Cl)nc1.NCc1ccc(C(F)(F)F)cc1 | NC(=O)c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1 | 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] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 7.4 | [{"value": 7.4, "product": "C1=CC(=CC=C1CNC2=NC=C(C=C2)C(=O)N)C(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.021 g, 0.03 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (4-(trifluoromethyl)phenyl)methanamine (0.097 mL, 0.68 mmol). The r... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | NC(=O)c1ccc(Cl)nc1.NCc1ccc(C(F)(F)F)cc1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].COCCOC>NC(=O)c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3a15989581314d86a106f9d713384402 | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N | COC1=C(C=C(C=C1)Br)C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]([C:21]#[N:22])[cH:19]1.[NH2:7][CH2:8][C@@H:9]([CH3:10])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][C@@H:9]([CH3:10])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]1[... | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C | COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N | 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 | c1ccccc1 | 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] | 47.64 | [{"value": 47.64, "product": "C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.529 g, 2.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.124 g, 2.36 mmol) were added in one portion to a degassed solution of 5-bromo-2-methoxybenzonitrile (5 g, 23.58 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (5.36 g, 28.30 mmol) and cesium carbonate (11.52 g, 35.37 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | 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 | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>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>COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9030d498cd864647879671340ebf8182 | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N | COC1=C(C=C(C=C1)Br)C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]([C:21]#[N:22])[cH:19]1.[NH2:7][CH2:8][C@@H:9]([CH3:10])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][C@@H:9]([CH3:10])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]1[... | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C | COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N | 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 | c1ccccc1 | 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] | 20.58 | [{"value": 20.58, "product": "C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Reaction carried PdOAc2 (0.476 g, 2.12 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.012 g, 2.12 mmol) were added in one portion to a degassed solution of 5-bromo-2-methoxybenzonitrile (4.50 g, 21.22 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (4.82 g, 25.47 mmol) and cesium carbo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | 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 | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>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>COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5c2ff1c91b594cd2a9a708b467e463cc | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N | COC1=C(C=C(C=C1)Br)C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]([C:21]#[N:22])[cH:19]1.[NH2:7][CH2:8][C@@H:9]([CH3:10])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][C@@H:9]([CH3:10])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]1[... | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C | COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N | 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 | c1ccccc1 | 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] | 62.19 | [{"value": 62.19, "product": "C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Trial reaction for PdOAc2 (0.021 g, 0.09 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.045 g, 0.09 mmol) were added in one portion to a degassed solution of 5-bromo-2-methoxybenzonitrile (0.200 g, 0.94 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.214 g, 1.13 mmol) and cesium ca... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | 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 | COc1ccc(Br)cc1C#N.C[C@H](CN)O[Si](C)(C)C(C)(C)C>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>COc1ccc(NC[C@@H](C)O[Si](C)(C)C(C)(C)C)cc1C#N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e89c2aa0807f47eabc561a9b2db7adf0 | CC(C)(C)OC(N)=O.COC(=O)c1ncc(Br)cn1>>COC(=O)c1ncc(NC(=O)OC(C)(C)C)cn1 | COC(=O)C1=NC=C(C=N1)Br.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=CN=C(N=C1)C(=O)OC | [NH2:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].Br[c:8]1[cH:7][n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:18][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18]1 | CC(C)(C)OC(N)=O.COC(=O)c1ncc(Br)cn1 | COC(=O)c1ncc(NC(=O)OC(C)(C)C)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 05dea0bfc992ec03c582f231be5f409d7ae874bdb1fbe422641877bf286598d1 | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1cncnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#7;a:8]:[c:9]:1.[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]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#7;a: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;... | 60.84 | [{"value": 60.84, "product": "CC(C)(C)OC(=O)NC1=CN=C(N=C1)C(=O)OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | The methyl 5-bromopyrimidine-2-carboxylate (1 g, 4.61 mmol), tert-butyl carbamate (0.756 g, 6.45 mmol), diacetoxypalladium (0.052 g, 0.23 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.267 g, 0.46 mmol), cesium carbonate (2.252 g, 6.91 mmol) and dioxane (15 mL) were placed and sealed into a microwa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CC(C)(C)OC(N)=O.COC(=O)c1ncc(Br)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1ncc(NC(=O)OC(C)(C)C)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f833eea6508044b8abf8f02c39f87010 | CC(C)(C)OC(N)=O.COC(=O)c1ncc(Br)cn1>>COC(=O)c1ncc(NC(=O)OC(C)(C)C)cn1 | COC(=O)C1=NC=C(C=N1)Br.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=CN=C(N=C1)C(=O)OC | [NH2:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].Br[c:8]1[cH:7][n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:18][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18]1 | CC(C)(C)OC(N)=O.COC(=O)c1ncc(Br)cn1 | COC(=O)c1ncc(NC(=O)OC(C)(C)C)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 05dea0bfc992ec03c582f231be5f409d7ae874bdb1fbe422641877bf286598d1 | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1cncnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#7;a:8]:[c:9]:1.[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]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#7;a: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;... | 64.27 | [{"value": 64.27, "product": "CC(C)(C)OC(=O)NC1=CN=C(N=C1)C(=O)OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | The methyl 5-bromopyrimidine-2-carboxylate (4 g, 18.43 mmol), tert-butyl carbamate (3.02 g, 25.80 mmol), diacetoxypalladium (0.207 g, 0.92 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.066 g, 1.84 mmol), cesium carbonate (9.01 g, 27.65 mmol) and dioxane (50 mL) were placed and sealed into a microw... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CC(C)(C)OC(N)=O.COC(=O)c1ncc(Br)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1ncc(NC(=O)OC(C)(C)C)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-980427b3cc854bc88aa11ec4ee256fb1 | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1>>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-c1cnn(C)c1 | CC1=CSC(=N1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CSC(=N1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC)C | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[c:28]1[cH:29][n:30][n:31]([CH3:32])[cH:33]1.Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[n:16][c:17]([CH3:18])[cH:19][s:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2>>[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]... | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1 | COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-c1cnn(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 | c1csc(C2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)cn4)nc3O2)n1 | 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] | 56.41 | [{"value": 56.41, "product": "CC1=CSC(=N1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC)C", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To 8-chloro-4-methyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (207 mg, 0.70 mmol) in DME (3 mL) were 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (143 mg, 0.70 mmol), cesium carbonate (342 mg, 1.05 mmol), 2-(Dicyclohexylphosphino)biphenyl (24.53 mg, 0.07 mmol) and Palladium acetat... | 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.c1cscn1.c1cn[nH]c1 | 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 | 110 | null | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1>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)OC(c2nc(C)cs2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b88a57a3139142d0b67529e7ea94eb7c | Cc1nc(N)oc1C.Clc1ccnc(Cl)c1>>Cc1nc(Nc2cc(Cl)ccn2)oc1C | C1=CN=C(C=C1Cl)Cl.CC1=C(OC(=N1)N)C>>CC1=C(OC(=N1)NC2=NC=CC(=C2)Cl)C | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[o:13][c:14]1[CH3:15].Cl[c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]2)[o:13][c:14]1[CH3:15] | Cc1nc(N)oc1C.Clc1ccnc(Cl)c1 | Cc1nc(Nc2cc(Cl)ccn2)oc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(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] | 15.2 | [{"value": 15.2, "product": "CC1=C(OC(=N1)NC2=NC=CC(=C2)Cl)C", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: Repeat of experiment in an attempt to improve isolated yield using different normal phase eluent system (isolation was problematic for ). Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 2,4-dichloropyridine (148 mg, 1.00 mmol), cesium carbonate (652 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | Cc1nc(N)oc1C.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cc1nc(Nc2cc(Cl)ccn2)oc1C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e66c732566f245d48f208bb758cb3489 | Cc1nc(N)oc1C.Clc1ccnc(Cl)c1>>Cc1nc(Nc2cc(Cl)ccn2)oc1C | C1=CN=C(C=C1Cl)Cl.CC1=C(OC(=N1)N)C>>CC1=C(OC(=N1)NC2=NC=CC(=C2)Cl)C | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[o:13][c:14]1[CH3:15].Cl[c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]2)[o:13][c:14]1[CH3:15] | Cc1nc(N)oc1C.Clc1ccnc(Cl)c1 | Cc1nc(Nc2cc(Cl)ccn2)oc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(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] | 15.2 | [{"value": 15.2, "product": "CC1=C(OC(=N1)NC2=NC=CC(=C2)Cl)C", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: To find out which substrates are efficient coupling partners, is there a robust link between how electron poor the substrate is and yield i.e. more electron poor aminooxazoles produce greater yields. Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 2,4... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | Cc1nc(N)oc1C.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cc1nc(Nc2cc(Cl)ccn2)oc1C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2bf055ae52c14e578ca506139e6af8cb | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1cn(-c2ccc(N)nc2)cn1>>Cc1cn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)nc2)cn1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=CN=C(C=C2)N>>CC1=CN(C=N1)C2=CN=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3 | Cl[c:10]1[cH:11][cH:12][c:13]2[c:14]([n:15]1)[O:16][C@H:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH2:24][N:25]([CH3:26])[CH2:27]2.[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH2:9])[n:28][cH:29]2)[cH:30][n:31]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]4[c:14]([n... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1cn(-c2ccc(N)nc2)cn1 | Cc1cn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)nc2)cn1 | 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] | 35.89 | [{"value": 35.89, "product": "CC1=CN(C=N1)C2=CN=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (129 mg, 0.47 mmol), 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (82 mg, 0.47 mmol), PALLADIUM(II) ACETATE (10.54 mg, 0.05 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (16.46 mg, 0.05 mmol) and Cs2CO3 (229 mg, 0.70 mmol) were weighed into a micro... | 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 | c1c[nH]cn1.c1ccncc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | 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.Cc1cn(-c2ccc(N)nc2)cn1>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>Cc1cn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)nc2)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6df914594aae4a42ba5b1bcb65424482 | Cc1cc(Cl)nc2c1CN(C)CC(CC(F)(F)F)O2.Cc1cn(-c2ccc(N)nc2)cn1>>Cc1cn(-c2ccc(Nc3cc(C)c4c(n3)OC(CC(F)(F)F)CN(C)C4)nc2)cn1 | CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)Cl.CC1=CN(C=N1)C2=CN=C(C=C2)N>>CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)NC3=NC=C(C=C3)N4C=C(N=C4)C | Cl[c:10]1[cH:11][c:12]([CH3:13])[c:14]2[c:15]([n:16]1)[O:17][CH:18]([CH2:19][C:20]([F:21])([F:22])[F:23])[CH2:24][N:25]([CH3:26])[CH2:27]2.[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH2:9])[n:28][cH:29]2)[cH:30][n:31]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[cH:11][c:12]([CH3:13])[c:14]... | Cc1cc(Cl)nc2c1CN(C)CC(CC(F)(F)F)O2.Cc1cn(-c2ccc(N)nc2)cn1 | Cc1cn(-c2ccc(Nc3cc(C)c4c(n3)OC(CC(F)(F)F)CN(C)C4)nc2)cn1 | 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 | c1cn(-c2ccc(Nc3ccc4c(n3)OCCNC4)nc2)cn1 | 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] | 15.45 | [{"value": 15.45, "product": "CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)NC3=NC=C(C=C3)N4C=C(N=C4)C", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To 8-chloro-4,6-dimethyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (300 mg, 0.51 mmol) in DME (4 mL) were 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (89 mg, 0.51 mmol), cesium carbonate (249 mg, 0.76 mmol), 2-(Dicyclohexylphosphino)biphenyl (17.84 mg, 0.05 mmol) and Palladium acetate (11.... | 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 | c1c[nH]cn1.c1ccncc1.c1cnc2c(c1)C[NH]CCO2 | 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 | 110 | null | Cc1cc(Cl)nc2c1CN(C)CC(CC(F)(F)F)O2.Cc1cn(-c2ccc(N)nc2)cn1>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>Cc1cn(-c2ccc(Nc3cc(C)c4c(n3)OC(CC(F)(F)F)CN(C)C4)nc2)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1525568325b3443390953fb89e1c826a | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Cl)cccc2o1>>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Cl.CC(C)(C)OC(=O)N1CCNCC1>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C | [NH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.Cl[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:... | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Cl)cccc2o1 | CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2ccoc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 63.8 | [{"value": 63.8, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | tert-butyl piperazine-1-carboxylate (5.22 g, 28.04 mmol), ethyl 4-chlorobenzofuran-2-carboxylate (6.3 g, 28.04 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (1.337 g, 2.80 mmol), Tris(dibenzylideneacetone)dipalladium(0) (1.284 g, 1.40 mmol) and CESIUM CARBONATE (11.88 g, 36.46 mmol) were heated u... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Cl)cccc2o1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-124e8e40d3e54042af531dbb1d8d85d1 | C1CNCCN1.N#Cc1ccc(Cl)cc1Br>>N#Cc1ccc(Cl)cc1N1CCNCC1 | C1=CC(=C(C=C1Cl)Br)C#N.C1CNCCN1>>C1CN(CCN1)C2=C(C=CC(=C2)Cl)C#N | [NH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1.Br[c:9]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6]([Cl:7])[cH:8]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[N:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | C1CNCCN1.N#Cc1ccc(Cl)cc1Br | N#Cc1ccc(Cl)cc1N1CCNCC1 | 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 | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1CN(CCN1)C2=C(C=CC(=C2)Cl)C#N", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Tris(dibenzylideneacetone)dipalladium (0) (43.4 mg, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (59.0 mg, 0.09 mmol) were added to a mixture of 2-bromo-4-chlorobenzonitrile (205 mg, 0.95 mmol), Cesium carbonate (463 mg, 1.42 mmol) and Piperazine (163 mg, 1.89 mmol) in dioxane (3 mL). Reaction vessel ... | 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 | 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 | 90 | null | C1CNCCN1.N#Cc1ccc(Cl)cc1Br>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>N#Cc1ccc(Cl)cc1N1CCNCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-91c1aa5c02fc46a586e9f5a373b7526a | C1CNCCN1.N#Cc1ccc(F)cc1Br>>N#Cc1ccc(F)cc1N1CCNCC1 | C1=CC(=C(C=C1F)Br)C#N.C1CNCCN1>>C1CN(CCN1)C2=C(C=CC(=C2)F)C#N | [NH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1.Br[c:9]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6]([F:7])[cH:8]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[N:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | C1CNCCN1.N#Cc1ccc(F)cc1Br | N#Cc1ccc(F)cc1N1CCNCC1 | 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 | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1CN(CCN1)C2=C(C=CC(=C2)F)C#N", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Tris(dibenzylideneacetone)dipalladium (0) (57.2 mg, 0.06 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (78 mg, 0.12 mmol) were added to a mixture of 2-bromo-4-fluorobenzonitrile (250 mg, 1.25 mmol), Cesium carbonate (611 mg, 1.87 mmol) and Piperazine (215 mg, 2.50 mmol) in dioxane (3 mL). Reaction vessel wa... | 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 | 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 | 90 | null | C1CNCCN1.N#Cc1ccc(F)cc1Br>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>N#Cc1ccc(F)cc1N1CCNCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-16b6dbfada904ea1b6f495fddc318fb3 | Clc1ccnc(Br)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Br.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Br[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Br)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | C1=CC=C(C=C1)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Br-[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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 0.5 | [{"value": 0.5, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 170 | CELSIUS | null | null | Objective: Improve yield of the desired product starting from the bromoaryl compound. To a flask containing 2-bromo-4-chloropyridine (196 mg, 1.02 mmol), sodium phenolate (177 mg, 1.52 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (11.63 mg, 0.01 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HBr | C1=CC=C(C=C1)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 170 | null | Clc1ccnc(Br)c1.Nc1ncco1>C1=CC=C(C=C1)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-25a2d29381d0432e90a88d041ce4da72 | Clc1ccnc(Br)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Br.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Br[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Br)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)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 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Br-[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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 7.67 | [{"value": 7.67, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: To find out if the 2-bromopyridine is a more efficient coupling partner than the chloro analogue. Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 2-bromo-4-chloropyridine (192 mg, 1.00 mmol), cesium carbonate (652 mg, 2.00 mmol) and oxazol-2-amine (84... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | Clc1ccnc(Br)c1.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.C1=CC=C(C=C1)/C=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>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-703c2a2b287b493ebc27b295a0de91ac | Clc1ccnc(Cl)c1.Nc1cccc([N+](=O)[O-])c1>>O=[N+]([O-])c1cccc(Nc2cc(Cl)ccn2)c1 | C1=CN=C(C=C1Cl)Cl.C1=CC(=CC(=C1)[N+](=O)[O-])N>>C1=CC(=CC(=C1)[N+](=O)[O-])NC2=NC=CC(=C2)Cl | Cl[c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][n:16]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[cH:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][n:16]2)[cH:17]1 | Clc1ccnc(Cl)c1.Nc1cccc([N+](=O)[O-])c1 | O=[N+]([O-])c1cccc(Nc2cc(Cl)ccn2)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 aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccn2)cc1 | 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] | 47.82 | [{"value": 47.82, "product": "C1=CC(=CC(=C1)[N+](=O)[O-])NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-Nitroaniline (140 mg, 1.01 mmol), 2,4-dichloropyridine (150 mg, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in dioxane (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.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 | Clc1ccnc(Cl)c1.Nc1cccc([N+](=O)[O-])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>O=[N+]([O-])c1cccc(Nc2cc(Cl)ccn2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4ae237ba7d264026afd182c3af660100 | CC(C)(C)OC(N)=O.COc1cc(N2CCN(C)CC2)c(Br)cc1N>>COc1cc(N2CCN(C)CC2)c(NC(=O)OC(C)(C)C)cc1N | CN1CCN(CC1)C2=C(C=C(C(=C2)OC)N)Br.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=C(C=C(C(=C1)N)OC)N2CCN(CC2)C | [NH2:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].Br[c:13]1[c:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)[cH:4][c:3]([O:2][CH3:1])[c:23]([NH2:24])[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)[c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([C... | CC(C)(C)OC(N)=O.COc1cc(N2CCN(C)CC2)c(Br)cc1N | COc1cc(N2CCN(C)CC2)c(NC(=O)OC(C)(C)C)cc1N | 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 | 6908f1dcf5268c746b7a7269b75335bd2fc1b14f2d985976d054ac2fda336d3a | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]):[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]>>[#7:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:13]-[C:12](=[O;D1;H0:14])-[#8:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)NC1=C(C=C(C(=C1)N)OC)N2CCN(CC2)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | To a suspension of 5-bromo-2-methoxy-4-(4-methylpiperazin-1-yl)aniline (50 mg, 0.17 mmol) in dioxane (4 mL) was added tert-butyl carbamate (24.39 mg, 0.21 mmol), cesium carbonate (81 mg, 0.25 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (19.27 mg, 0.03 mmol). The resulting suspension was degassed and Palla... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CC(C)(C)OC(N)=O.COc1cc(N2CCN(C)CC2)c(Br)cc1N>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc(N2CCN(C)CC2)c(NC(=O)OC(C)(C)C)cc1N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-86909c5b2c9143b3acd377f2edc373e3 | CN1CCC(Oc2cccc(N)c2)CC1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1>>Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(OC3CCN(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.CN1CCC(CC1)OC2=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)OC6CCN(CC6)C | [NH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]([O:34][CH: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:43... | CN1CCC(Oc2cccc(N)c2)CC1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1 | Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(OC3CCN(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(OC3CCNCC3)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] | 32.84 | [{"value": 32.84, "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)OC6CCN(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-(1-methylpiperidin-4-yloxy)aniline (36.5 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 µmol)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2c(c1)OCCO2.c1ccncc1.c1ccccc1.C1CC[NH]CC1 | 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 | CN1CCC(Oc2cccc(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-6b87f2a7230043c19d1f4cb86bf0930a | CN(C)Cc1cccc(N)c1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1>>Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(CN(C)C)c2)nc1 | CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl.CN(C)CC1=CC(=CC=C1)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)CN(C)C | [NH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]([CH2:34][N:35]([CH3:36])[CH3:37])[cH:38]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:40][n:39]1>>[CH3:1][c:2]1[cH:3][cH:4][c... | CN(C)Cc1cccc(N)c1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1 | Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(CN(C)C)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(Nc2ccccc2)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] | 38.79 | [{"value": 38.79, "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)CN(C)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-((dimethylamino)methyl)aniline (26.6 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 µmol),sod... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2c(c1)OCCO2.c1ccncc1.c1ccccc1 | 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 | CN(C)Cc1cccc(N)c1.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=C1>Cc1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-68539516fcd24378954aa9ca9f44991e | CN(C)C1CCN(c2cccc(N)c2)C1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1>>Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(N3CCC(N(C)C)C3)c2)nc1 | CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl.CN(C)C1CCN(C1)C2=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)N6CCC(C6)N(C)C | [NH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]([N:34]2[CH2:35][CH2:36][CH:37]([N:38]([CH3:39])[CH3:40])[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:... | CN(C)C1CCN(c2cccc(N)c2)C1.Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Cl)nc1 | Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1NC(=O)c1ccc(Nc2cccc(N3CCC(N(C)C)C3)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(N3CCCC3)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] | 10.22 | [{"value": 10.22, "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)N6CCC(C6)N(C)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 (70 mg, 0.17 mmol),[Reactants],(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.73 mg, 9.91 µmol),TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (4.54 mg, 4.95 µmol),sodium 2-methylpropan-2-olate (23.81 mg, 0.25... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2c(c1)OCCO2.c1ccncc1.c1ccccc1.C1CC[NH]C1 | 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 | CN(C)C1CCN(c2cccc(N)c2)C1.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=C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2b17d1283fc34150bab8e6391b459594 | Cc1coc(N)n1.Clc1ccnc(Cl)c1>>Cc1coc(Nc2cc(Cl)ccn2)n1 | C1=CN=C(C=C1Cl)Cl.CC1=COC(=N1)N>>CC1=COC(=N1)NC2=NC=CC(=C2)Cl | [CH3:1][c:2]1[cH:3][o:4][c:5]([NH2:6])[n:14]1.Cl[c:7]1[cH:8][c:9]([Cl:10])[cH:11][cH:12][n:13]1>>[CH3:1][c:2]1[cH:3][o:4][c:5]([NH:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][n:13]2)[n:14]1 | Cc1coc(N)n1.Clc1ccnc(Cl)c1 | Cc1coc(Nc2cc(Cl)ccn2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=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] | 28.14 | [{"value": 28.14, "product": "CC1=COC(=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: To find out which substrates are efficient coupling partners, is there a robust link between how electron poor the substrate is and yield i.e. more electron poor aminooxazoles produce greater yields. Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 2,4... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | Cc1coc(N)n1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Cc1coc(Nc2cc(Cl)ccn2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-29d169023edf45ffb5746904d99b3825 | Brc1cncc(Br)c1.CO[C@@H]1CCNC1>>CO[C@@H]1CCN(c2cncc(Br)c2)C1 | C1=C(C=NC=C1Br)Br.CO[C@@H]1CCNC1>>CO[C@@H]1CCN(C1)C2=CC(=CN=C2)Br | Br[c:7]1[cH:8][n:9][cH:10][c:11]([Br:12])[cH:13]1.[CH3:1][O:2][C@@H:3]1[CH2:4][CH2:5][NH:6][CH2:14]1>>[CH3:1][O:2][C@@H:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][n:9][cH:10][c:11]([Br:12])[cH:13]2)[CH2:14]1 | Brc1cncc(Br)c1.CO[C@@H]1CCNC1 | CO[C@@H]1CCN(c2cncc(Br)c2)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 | 4ce7f1716cd0b0bc1bd76f94962fe45a1bd7fe2a7a90867b0ae7b00b6ffc65fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#7;a:5]1:[c:4]:[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]:1 | 51.14 | [{"value": 51.14, "product": "CO[C@@H]1CCN(C1)C2=CC(=CN=C2)Br", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A mixture of 3,5-dibromopyridine (0.644 g, 2.72 mmol), (R)-3-methoxypyrrolidine (0.25 g, 2.47 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.045 g, 0.05 mmol), sodium 2-methylpropan-2-olate (0.356 g, 3.71 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.077 g, 0.12 mmol) in degassed toluene (7.5 ml) was sealed... | 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 | 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 | 90 | null | Brc1cncc(Br)c1.CO[C@@H]1CCNC1>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>CO[C@@H]1CCN(c2cncc(Br)c2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a1449f92bd2f4287a8b4f60d1e409d2f | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 68.31 | [{"value": 68.31, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (1.198 g, 5.34 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (2.54 g, 5.34 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (15.00 g, 53.36 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (12.63 g, 66.70 mmol) and cesium carbonate (26.... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0601bc9f7aa7425cb05cd1af50678356 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 61.41 | [{"value": 61.41, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.080 g, 0.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.170 g, 0.36 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1 g, 3.56 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.674 g, 3.56 mmol) and cesium carbonate (1.739 g,... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1df10534bfeb467c9df72e530f4b3ab2 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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 | 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] | 0 | [{"value": 0.0, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.080 g, 0.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.170 g, 0.36 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1 g, 3.56 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.808 g, 4.27 mmol) and cesium carbonate (1.739 g,... | 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].C1COCCO1 | 120 | null | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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].C1COCCO1>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-13647a5d8826486e986a33a5850b535a | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 67.69 | [{"value": 67.69, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.799 g, 3.56 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.696 g, 3.56 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (10.00 g, 35.57 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (8.08 g, 42.69 mmol) and cesium carbonate (17.... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e216d528807c48f991f68bcf4d0ec14d | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 68.55 | [{"value": 68.55, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (1.198 g, 5.34 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (2.54 g, 5.34 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (15.00 g, 53.36 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (12.63 g, 66.70 mmol) and cesium carbonate (26.... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3b6fe99cd0a6495daf0c56d94f8acbcc | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 69.56 | [{"value": 69.56, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.040 g, 0.18 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.085 g, 0.18 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (0.500 g, 1.78 mmol), [Reactants] and cesium carbonate (0.869 g, 2.67 mmol) in toluene (15 mL) at 20°C in a microwave v... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-611f7690ba1449b3a297ce2aee3500c7 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 64.8 | [{"value": 64.8, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.799 g, 3.56 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.696 g, 3.56 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (10.00 g, 35.57 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (8.08 g, 42.69 mmol) and cesium carbonate (17.... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-096c3c09227841d997327413bc9951b7 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 73.6 | [{"value": 73.6, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "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), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (3.37 g, 17.79 mmol) and cesium carbonate (8.69... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5baedbe69f7740f6b5f0fde32453a3b3 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 72.88 | [{"value": 72.88, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.799 g, 3.56 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.696 g, 3.56 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (10.00 g, 35.57 mmol), 1-(benzyloxy)-4-bromo-2-fluorobenzene (10.00 g, 35.57 mmol) and cesium carbonate (17.39 g, 53.36... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e7f2690304e449cfaae6138b77013850 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([F:18])[cH:19]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1 | C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C | 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] | 67.5 | [{"value": 67.5, "product": "C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.124 g, 0.55 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.263 g, 0.55 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1.550 g, 5.51 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (1.044 g, 5.51 mmol) and cesium carbonate (2.69... | 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 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.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>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-507c2159372a46eb8fb0f4b142612613 | Brc1ccc(OCc2ccccc2)cc1.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNc1ccc(OCc2ccccc2)cc1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=CC=C(C=C2)Br.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC=C(C=C1)OCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C | Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1.[CH3:1][C@H:2]([CH2:3][NH2:4])[O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26]>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18... | Brc1ccc(OCc2ccccc2)cc1.C[C@H](CN)O[Si](C)(C)C(C)(C)C | C[C@H](CNc1ccc(OCc2ccccc2)cc1)O[Si](C)(C)C(C)(C)C | 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] | 65.15 | [{"value": 65.15, "product": "C[C@H](CNC1=CC=C(C=C1)OCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Palladium(II) acetate (0.427 g, 1.90 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.906 g, 1.90 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromobenzene (5 g, 19.00 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (4.32 g, 22.80 mmol) and Cesium carbonate (... | 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 | Brc1ccc(OCc2ccccc2)cc1.C[C@H](CN)O[Si](C)(C)C(C)(C)C>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>C[C@H](CNc1ccc(OCc2ccccc2)cc1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d683d9b583de441b8565719233e1bd75 | Brc1ccc(OCc2ccccc2)cc1.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNc1ccc(OCc2ccccc2)cc1)O[Si](C)(C)C(C)(C)C | C1=CC=C(C=C1)COC2=CC=C(C=C2)Br.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC=C(C=C1)OCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C | Br[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1.[CH3:1][C@H:2]([CH2:3][NH2:4])[O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26]>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18... | Brc1ccc(OCc2ccccc2)cc1.C[C@H](CN)O[Si](C)(C)C(C)(C)C | C[C@H](CNc1ccc(OCc2ccccc2)cc1)O[Si](C)(C)C(C)(C)C | 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] | 18.88 | [{"value": 18.88, "product": "C[C@H](CNC1=CC=C(C=C1)OCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Reaction carried out as follows: PdOAc2 (0.768 g, 3.42 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.631 g, 3.42 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromobenzene (9.00 g, 34.20 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (7.77 g, 41.04 mmol) a... | 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 | Brc1ccc(OCc2ccccc2)cc1.C[C@H](CN)O[Si](C)(C)C(C)(C)C>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>C[C@H](CNc1ccc(OCc2ccccc2)cc1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-debb5d422e4240d09a376a4606e5e57f | Clc1ccnc(Cl)c1.Nc1nc(C(F)(F)F)co1>>FC(F)(F)c1coc(Nc2cc(Cl)ccn2)n1 | C1=CN=C(C=C1Cl)Cl.C1=C(N=C(O1)N)C(F)(F)F>>C1=CN=C(C=C1Cl)NC2=NC(=CO2)C(F)(F)F | Cl[c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][n:16]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][o:7][c:8]([NH2:9])[n:17]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][o:7][c:8]([NH:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][n:16]2)[n:17]1 | Clc1ccnc(Cl)c1.Nc1nc(C(F)(F)F)co1 | FC(F)(F)c1coc(Nc2cc(Cl)ccn2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 17.45 | [{"value": 17.45, "product": "C1=CN=C(C=C1Cl)NC2=NC(=CO2)C(F)(F)F", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Repeat of EN04881-41 to get pure sample of product in potentially higher isolated yield. cesium carbonate (652 mg, 2.00 mmol), Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 4-(trifluoromethyl)oxazol-2-amine (152 mg, 1.00 mmol) and 2,4-dichloropyridine (148 mg,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | Clc1ccnc(Cl)c1.Nc1nc(C(F)(F)F)co1>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>FC(F)(F)c1coc(Nc2cc(Cl)ccn2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cc7dfeae12f6444baf8a8a863fd60e2b | Fc1ccc(Br)cc1.O=C1CNCCN1>>O=C1CN(c2ccc(F)cc2)CCN1 | C1=CC(=CC=C1F)Br.C1CNC(=O)CN1>>C1CN(CC(=O)N1)C2=CC=C(C=C2)F | Br[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1.[O:1]=[C:2]1[CH2:3][NH:4][CH2:12][CH2:13][NH:14]1>>[O:1]=[C:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[CH2:12][CH2:13][NH:14]1 | Fc1ccc(Br)cc1.O=C1CNCCN1 | O=C1CN(c2ccc(F)cc2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d7148bc7995d5dfa1607e72989e75c64b789e6aafbd2cc3ab6637dcd843b0985 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C1CN(c2ccccc2)CCN1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-1 | 0 | [{"value": 0.0, "product": "C1CN(CC(=O)N1)C2=CC=C(C=C2)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | diacetoxypalladium (11.21 mg, 0.05 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.9 mg, 0.05 mmol) were dissolved in toluene (0.5 mL) under nitrogen. Stirred at 50C for 30min. sodium 2-methylpropan-2-olate (96 mg, 1.00 mmol) and piperazin-2-one (50 mg, 0.50 mmol) were added to a second microwa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCCN1 | C1CNCC[NH]1.c1ccccc1 | C1CNCC[NH]1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 150 | null | Fc1ccc(Br)cc1.O=C1CNCCN1>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>O=C1CN(c2ccc(F)cc2)CCN1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1f028ee237f04c2e9096e33f82aadddf | Fc1ccc(Br)cc1.O=C1CNCCN1>>O=C1CN(c2ccc(F)cc2)CCN1 | C1=CC(=CC=C1F)Br.C1CNC(=O)CN1>>C1CN(CC(=O)N1)C2=CC=C(C=C2)F | Br[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1.[O:1]=[C:2]1[CH2:3][NH:4][CH2:12][CH2:13][NH:14]1>>[O:1]=[C:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[CH2:12][CH2:13][NH:14]1 | Fc1ccc(Br)cc1.O=C1CNCCN1 | O=C1CN(c2ccc(F)cc2)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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d7148bc7995d5dfa1607e72989e75c64b789e6aafbd2cc3ab6637dcd843b0985 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C1CN(c2ccccc2)CCN1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-1 | 0 | [{"value": 0.0, "product": "C1CN(CC(=O)N1)C2=CC=C(C=C2)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | diacetoxypalladium (11.21 mg, 0.05 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.9 mg, 0.05 mmol) were dissolved in toluene (0.5 mL) under nitrogen. Stirred at 50C for 30min. sodium 2-methylpropan-2-olate (96 mg, 1.00 mmol) and piperazin-2-one (50 mg, 0.50 mmol) were added to a second microwa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCCN1 | C1CNCC[NH]1.c1ccccc1 | C1CNCC[NH]1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 150 | null | Fc1ccc(Br)cc1.O=C1CNCCN1>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>O=C1CN(c2ccc(F)cc2)CCN1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8809d217cb404d41bb5809dd5f95b269 | Fc1ccc(Br)cc1.c1ccc(CN2CCNCC2)cc1>>Fc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | C1=CC(=CC=C1F)Br.C1CN(CCN1)CC2=CC=CC=C2>>C1CN(CCN1CC2=CC=CC=C2)C3=CC=C(C=C3)F | Br[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:20][cH:19]1.[NH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20]1 | Fc1ccc(Br)cc1.c1ccc(CN2CCNCC2)cc1 | Fc1ccc(N2CCN(Cc3ccccc3)CC2)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 | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3ccccc3)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 74.98 | [{"value": 74.98, "product": "C1CN(CCN1CC2=CC=CC=C2)C3=CC=C(C=C3)F", "details": "", "is_desired": true}] | 50 | CELSIUS | null | null | diacetoxypalladium (12.74 mg, 0.06 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (32.8 mg, 0.06 mmol) were suspended in toluene (0.5 mL) under N2. Heated to 50C for 30 min (microwave). sodium 2-methylpropan-2-olate (109 mg, 1.13 mmol) was suspended in toluene (0.500 mL) under N2. 1-benzylpiperazi... | 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.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 50 | null | Fc1ccc(Br)cc1.c1ccc(CN2CCNCC2)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>Fc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f55732d796df4a6bad136ec929c58223 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | 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] | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 0 | [{"value": 0.0, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Charged a standard microwave vial with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (100 mg, 0.49 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (135 mg, 0.49 mmol), cesium carbonate (239 mg, 0.73 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.42 mg, 0.02 ... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].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] | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].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]>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ab90c7bf1414400583ffe823e3ef21b5 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[K+].[K+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COC1=CC=CC=C1 | 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].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Objective: Repeat of optimised conditions found in process research and devellopment screen for an isolated yield. An activated catalyst solution was prepared by adding TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (61.3 mg, 0.07 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (77 mg, 0.13 mmol) to an o... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1 | 90 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ea8e215424fc4a3cbe2138b915565d9a | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[K+].[K+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COC1=CC=CC=C1 | 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].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Objective: Repeat of optimised conditions found in process research and devellopment screen for an isolated yield. An activated catalyst solution was prepared by adding TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (61.3 mg, 0.07 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (77 mg, 0.13 mmol) to an o... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1 | 120 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9c70bda080d74777b8199520e4c33326 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 44.34 | [{"value": 44.34, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Peparation of the above coupled product on a larger scale for hydrolysis-protodecarboxylation study. To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (546 mg, 3.50 mmol), 2,4-dichloropyridine (0.378 mL, 3.50 mmol), cesium carbonate (2279 mg, 6.99 mmol), TRIS(DIBENZYLIDENEACETONE)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 160 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5d8d88656735435b992c60c9f2e9cc2e | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 95.3 | [{"value": 95.3, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: To make the coupled product on a larger scale for hydrolysis/decarboxylation Pd2(dba)3 (80 mg, 0.09 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (152 mg, 0.26 mmol), 2,4-dichloropyridine (0.378 mL, 3.50 mmol), cesium carbonate (2279 mg, 6.99 mmol) and ethyl 2-aminooxazole-5-carboxylate (546 mg, 3.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 160 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1a79f6eb953447079285f217f58a9d53 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 41.51 | [{"value": 41.51, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: Poisoning experiment to find out if 2-aminooxazole or the coupled product from reaction of 2-aminooxazole and 2,4-dichloropyridine are 'poisoning' the catalyst. Reaction (a): Control reaction under identical conditions to EN04881-40 (should produce similar yield) Reaction (b): As for control but spiked wi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e464c7497c0f42409f807567be2bf47a | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 50.48 | [{"value": 50.48, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: To find out if the regioisomeric ester is also a reaction substrate in this C-N bond forming reaction Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 2,4-dichloropyridine (148 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol),ethyl 2-aminooxazole-5... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0fa704c187644f658d22f391e350db77 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)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] | 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].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Series of experiments to optimise yield of the above coupled product. Pd2(dba)3 (22.89 mg, 0.025 mmol), di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (42.4 mg, 0.10 mmol), 2,4-dichloropyridine (148 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol),ethyl 2-aminooxazole-5-carboxylate (156 mg,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)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].C1COCCO1 | 160 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)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].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-81c9dfb0f9224007985242064ea9e33c | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)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].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Series of experiments to optimise yield of the above coupled product. Pd2(dba)3 (22.89 mg, 0.025 mmol), di-tert- butyl(2',4',6'-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (48.4 mg, 0.10 mmol), 2,4-dichloropyridine (148 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol),ethyl 2-aminooxazole-5-carbox... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)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 | 160 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)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>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f5babb1245424d42a4fc7bc229425c40 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Series of experiments to optimise yield of the above coupled product. Pd2(dba)3 (22.89 mg, 0.025 mmol), bis(3,5-bis(trifluoromethyl)phenyl)(2',4',6'-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (80 mg, 0.10 mmol), 2,4-dichloropyridine (148 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol),ethyl 2-am... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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 | 160 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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>CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b82571e96a704ae5a3aea3ab951d01e7 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 49.92 | [{"value": 49.92, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Isolate a larger quantity of product for hydrolysis/decarboxylation study Pd2(dba)3 (91 mg, 0.10 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (173 mg, 0.30 mmol), 2,4-dichloropyridine (591 mg, 4.00 mmol), cesium carbonate (2604 mg, 7.99 mmol) and ethyl 2-aminooxazole-5-carboxylate (624 mg, 4.00 mm... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 160 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0e2b144c96fd4ac8aced468951db5ce4 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Attempt to synthesise the 4-substituted product using jackiephos as ligand. To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), 2,4-dichloropyridine (0.108 mL, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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 | 160 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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>CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-345c2935b6ec4f748049eeb832f405b7 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[o:18]1 | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 47.86 | [{"value": 47.86, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Objective: Comparison of the reactivity of 2-aminooxazole and ester substituted 2-aminooxazole under identical reaction conditions. To an oven-dried round bottomed flask was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | CCOC(=O)c1cnc(N)o1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(Cl)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bc0ccb3ec3974a6197509c6aeefd5c4d | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | C(=O)([O-])[O-].[K+].[K+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COC1=CC=CC=C1 | 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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 49.6 | [{"value": 49.6, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Objective: Repeat of optimised conditions found in process research and devellopment screen for an isolated yield. An activated catalyst solution was prepared by adding TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (61.3 mg, 0.07 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (77 mg, 0.13 mmol) to an o... | 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+].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].COC1=CC=CC=C1 | 120 | null | Clc1ccnc(Cl)c1.Nc1ncco1>C(=O)([O-])[O-].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COC1=CC=CC=C1>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-de391e2f60334b77bfa7be520f63a36b | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: Reactions using ligands not previously tested under these conditions 2,4-dichloropyridine (0.109 mL, 1.01 mmol), oxazol-2-amine (85 mg, 1.01 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (23.20 mg, 0.03 mmol), bis(3,5-bis(trifluoromethyl)phenyl)(2',4',6'-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (... | 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+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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 | 140 | null | Clc1ccnc(Cl)c1.Nc1ncco1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)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>Clc1ccnc(Nc2... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bc6c718e90df4b2591cc2506c375ce3f | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)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 | 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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 2.02 | [{"value": 2.02, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: To isolate some of the required product to provide an analytical sample for a large catalyst screen. 2,4-dichloropyridine (0.109 mL, 1.01 mmol), oxazol-2-amine (85 mg, 1.01 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.89 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (44.0 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | Clc1ccnc(Cl)c1.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.C1=CC=C(C=C1)/C=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>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-76fdaa39a364497293ede72dc7b21aee | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | [H-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 3.03 | [{"value": 3.03, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Objective: If deprotonation is rate-determining in this coupling quantitative deprotonation prior to subjection to coupling conditions should prove beneficial. To an oven dried microwave vial was added oxazol-2-amine (85 mg, 1.01 mmol) together with sodium hydride (40.5 mg, 1.01 mmol), the vial was capped and purged w... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | [H-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | Clc1ccnc(Cl)c1.Nc1ncco1>[H-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4973899cb35d49cd8a53a56048cd33f7 | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | 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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Will increased catalyst loading lead to increased isolated yield of the desired product? 2,4-dichloropyridine (0.109 mL, 1.01 mmol), oxazol-2-amine (102 mg, 1.22 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (186 mg, 0.20 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (352 mg, 0.61 mmol)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 160 | null | Clc1ccnc(Cl)c1.Nc1ncco1>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4ba5714524f04061a19a2e24cddcf117 | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a vial containing oxazol-2-amine (102 mg, 1.22 mmol), , TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (9.28 mg, 10.14 µmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (9.47 mg, 0.02 mmol) and sodium 2-methylpropan-2-olate (136 mg, 1.42 mmol), was added degassed toluene (4 mL) and 2,4-dichloropyridine (0.109 ml, 1.01 mm... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | Clc1ccnc(Cl)c1.Nc1ncco1>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>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-db4d850d1c594ca584a3d40b664f692e | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | C1=CC=C(C=C1)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 3.03 | [{"value": 3.03, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | To a microwave vial containing 2,4-dichloropyridine (0.109 mL, 1.01 mmol), sodium phenolate (177 mg, 1.52 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (11.60 mg, 0.01 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.59 mg, 0.03 mmol) (Xantphos), was added degassed dioxane (4 mL) and the mixtur... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | C1=CC=C(C=C1)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 130 | null | Clc1ccnc(Cl)c1.Nc1ncco1>C1=CC=C(C=C1)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5dfaf464504c42b7bafec75259e5a214 | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)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 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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 11.1 | [{"value": 11.1, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (11.38 mg, 0.05 mmol) was added in a single portion to a degassed solution of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (44.0 mg, 0.08 mmol), oxazol-2-amine (85 mg, 1.01 mmol), cesium carbonate (768 mg, 2.36 mmol),2,4-dichloropyridine (0.109 mL, 1.01 mmol), dioxane (4 mL) and DMSO (0.8 mL) a... | 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 | Clc1ccnc(Cl)c1.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>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1cd8c235ce4f4167a93c6067f176b339 | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)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] | CC(=O)N(C)C | 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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 1.97 | [{"value": 1.97, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | oxazol-2-amine (85 mg, 1.01 mmol), 2,4-dichloropyridine (0.151 mL, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in DMA (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) was a... | 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].CC(=O)N(C)C | 100 | null | Clc1ccnc(Cl)c1.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].CC(=O)N(C)C>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cab6249a1023430399dca1061d293aa8 | Clc1ccnc(Cl)c1.Nc1ncco1>>Clc1ccnc(Nc2ncco2)c1 | C1=CN=C(C=C1Cl)Cl.C1=COC(=N1)N>>C1=CN=C(C=C1Cl)NC2=NC=CO2 | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:13]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][o:12]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][o:12]2)[cH:13]1 | Clc1ccnc(Cl)c1.Nc1ncco1 | Clc1ccnc(Nc2ncco2)c1 | C1=CC=C(C=C1)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[#7;a:2]:[c:3] | 2.52 | [{"value": 2.52, "product": "C1=CN=C(C=C1Cl)NC2=NC=CO2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | To a flask containing 2,4-dichloropyridine (0.109 mL, 1.01 mmol), sodium phenolate (177 mg, 1.52 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (11.60 mg, 0.01 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.59 mg, 0.03 mmol) (Xantphos), was added degassed dioxane (4 mL) and the mixture allowed... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | C1=CC=C(C=C1)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 80 | null | Clc1ccnc(Cl)c1.Nc1ncco1>C1=CC=C(C=C1)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>Clc1ccnc(Nc2ncco2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-09bc2ed031574d359c24db47dee15c88 | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | C1=CC(=CC(=C1)OC(F)(F)F)C2=CN=C3N2N=C(C=C3)Cl.CN1CCC(CC1)CN>>CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2 | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH2:7])[CH2:28][CH2:29]1.Cl[c:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25]3)[n:26]2[n:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH:7][c:8]2[cH:9][cH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][... | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1 | CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 5eed801a0789ef0cf61beb455d5838de5141d4142ef2b34b7746111b27c744b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc3ccc(NCC4CCNCC4)nn23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1 | 35.87 | [{"value": 35.87, "product": "CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A 300 ml round bottom lfask was charged with a magnetic stir bar, toluene (39 ml), 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (1.1 g, 3.51 mmol), Pd2(dba)3 (0.321 g, 0.35 mmol), 2-(DIMETHYLAMINO)-2'-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (0.414 g, 1.05 mmol), SODIUM TERT-BUTOXIDE (1.011 g, 10.52 mmol), an... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnn2ccnc2c1 | c1cnn2ccnc2c1 | C1CC[NH]CC1.c1cnn2ccnc2c1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f81a599dec2242abb77d43e5f1e1fdd1 | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | C1=CC(=CC(=C1)OC(F)(F)F)C2=CN=C3N2N=C(C=C3)Cl.CN1CCC(CC1)CN>>CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2 | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH2:7])[CH2:28][CH2:29]1.Cl[c:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25]3)[n:26]2[n:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][NH:7][c:8]2[cH:9][cH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][... | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1 | CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 5eed801a0789ef0cf61beb455d5838de5141d4142ef2b34b7746111b27c744b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc3ccc(NCC4CCNCC4)nn23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1 | 62.89 | [{"value": 62.89, "product": "CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | A 500 ml round bottom lfask was charged with a magnetic stir bar, toluene (200 ml), 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (6.55 g, 20.88 mmol), Pd2dba3 (1.912 g, 2.09 mmol), fresh bottle of 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (2.465 g, 6.26 mmol), SODIUM TERT-BUTOXIDE (8.03... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnn2ccnc2c1 | c1cnn2ccnc2c1 | C1CC[NH]CC1.c1cnn2ccnc2c1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 120 | null | CN1CCC(CN)CC1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CN1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8ca29ea3c13d4e5098dc08cfe112f4d1 | Cc1ccc([N+](=O)[O-])cc1Br.Cc1ccc2cc(C(N)=O)ccc2n1>>Cc1ccc2cc(C(=O)Nc3cc([N+](=O)[O-])ccc3C)ccc2n1 | CC1=C(C=C(C=C1)[N+](=O)[O-])Br.CC1=NC2=C(C=C1)C=C(C=C2)C(=O)N>>CC1=C(C=C(C=C1)[N+](=O)[O-])NC(=O)C2=CC3=C(C=C2)N=C(C=C3)C | Br[c:11]1[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19]1[CH3:20].[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[NH2:10])[cH:21][cH:22][c:23]2[n:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]3[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19]3[CH3:20])[cH:21][cH... | Cc1ccc([N+](=O)[O-])cc1Br.Cc1ccc2cc(C(N)=O)ccc2n1 | Cc1ccc2cc(C(=O)Nc3cc([N+](=O)[O-])ccc3C)ccc2n1 | 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 | fa5dca18ce81184d7ec705aef53e02949f2d055b9a13e4c47aac4f58e325b293 | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1ccccc1)c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[NH2;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "CC1=C(C=C(C=C1)[N+](=O)[O-])NC(=O)C2=CC3=C(C=C2)N=C(C=C3)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (9.10 mg, 9.94 µmol) was added to 2-bromo-1-methyl-4-nitrobenzene (42.9 mg, 0.20 mmol), 2-methylquinoline-6-carboxamide (37.0 mg, 0.20 mmol), cesium carbonate (194 mg, 0.60 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (11.50 mg, 0.02 mmol) in dioxane (2 mL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | Cc1ccc([N+](=O)[O-])cc1Br.Cc1ccc2cc(C(N)=O)ccc2n1>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>Cc1ccc2cc(C(=O)Nc3... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-afce2c60bcdc4fe1bfc6b3962146067d | CC(=O)Nc1cc(N)ccc1N1CC[C@@H](NC(=O)OC(C)(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CC[C@@H](N)C1 | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N2CC[C@H](C2)NC(=O)OC(C)(C)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CC[C@H](C5)N | CC(C)(C)OC(=O)[NH:31][C@@H:30]1[CH2:29][CH2:28][N:27]([c:26]2[c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:6][c:7]([NH2:8])[cH:24][cH:25]2)[CH2:32]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[n:16]2[n:17][cH:18][c:19]([C:20]#[N:21])[c:22]2[n:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11... | CC(=O)Nc1cc(N)ccc1N1CC[C@@H](NC(=O)OC(C)(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CC[C@@H](N)C1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)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] | CN1CCCC1=O | Heteroatom Alkylation and Arylation | OtherReaction | 9a4f65309185583ef16d463802e592b98b41132bb5f5cb163af85532297ccacc | b189e21881719932ff7e93d2cee73d5d9b679e27f974877dd5fa270130c3c7ff | c1cc2nc(Nc3ccc(N4CCCC4)cc3)cc(NC3CC3)n2n1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9].Cl-[c;H0;D3;+0:10]1:[#7;a:11]:[c:12]2:[c:13]:[c:14]:[#7;a:15]:[#7;a:16]:2:[c:17](-[#7:18]):[c:19]:1>>[#7:5]-[C:4]-[C:2](-[NH2;D1;+0:1])-[C:3].[#7:18]-[c:17]1:[c:19]:[c;H0;D3;+0:10](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:11]:... | 17.82 | [{"value": 17.82, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CC[C@H](C5)N", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (300 mg, 1.28 mmol), (R)-tert-butyl 1-(2-acetamido-4-aminophenyl)pyrrolidin-3-ylcarbamate (429 mg, 1.28 mmol), CESIUM CARBONATE (837 mg, 2.57 mmol) and di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (54.5 mg, 0.13 mmol) were added into N... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester.Ether.Primary amine.Boc | Primary amine.Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1.C1CC[NH]C1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)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].CN1CCCC1=O | 105 | null | CC(=O)Nc1cc(N)ccc1N1CC[C@@H](NC(=O)OC(C)(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)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].CN1CCCC1=O>CC(=O)Nc1cc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-977ea289d9154a71ab2d4b28b571f050 | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1>>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.CC(C)(C)OC(=O)N1CCNCC1>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C | [NH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:... | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1 | CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2ccoc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 71.15 | [{"value": 71.15, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | tert-butyl piperazine-1-carboxylate (0.692 g, 3.72 mmol), ethyl 4-bromobenzofuran-2-carboxylate (1 g, 3.72 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.177 g, 0.37 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.170 g, 0.19 mmol) and CESIUM CARBONATE (1.574 g, 4.83 mmol) were heated under ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a752f4a96bed42979fc54c8d98f05186 | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1>>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.CC(C)(C)OC(=O)N1CCNCC1>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C | [NH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:... | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1 | CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2ccoc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 45.92 | [{"value": 45.92, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | ethyl 4-bromobenzofuran-2-carboxylate (7.7 g, 28.61 mmol), tert-butyl piperazine-1-carboxylate (5.33 g, 28.61 mmol), Tris(dibenzylideneacetone)dipalladium(0) (1.310 g, 1.43 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (1.364 g, 2.86 mmol) and CESIUM CARBONATE (12.12 g, 37.20 mmol) in dioxane (40... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fd5224e743de478bae3b0301ad531f8f | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1>>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.CC(C)(C)OC(=O)N1CCNCC1>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C | [NH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:... | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1 | CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2ccoc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 44.92 | [{"value": 44.92, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | ethyl 4-bromobenzofuran-2-carboxylate (2 g, 7.43 mmol), tert-butyl piperazine-1-carboxylate (1.384 g, 7.43 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.340 g, 0.37 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.354 g, 0.74 mmol) and CESIUM CARBONATE (3.15 g, 9.66 mmol) were heated under a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1cc2c(Br)cccc2o1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-62cd397fe6424e97abf226dd021d8df0 | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1ccc(=O)n(C)c1>>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1ccc(=O)n(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F.CN1C=C(C=CC1=O)C2=C(N=C(C=C2)N)OC>>CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(C(=O)C=C4)C)OC)CC(F)(F)F | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH2:20][N:21]([CH3:22])[CH2:23]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:24][cH:25][c:26]1-[c:27]1[cH:28][cH:29][c:30](=[O:31])[n:32]([CH3:33])[cH:34]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... | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1ccc(=O)n(C)c1 | COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1ccc(=O)n(C)c1 | CCC(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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1ccc(-c2ccc(Nc3ccc4c(n3)OCCNC4)nc2)c[nH]1 | 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] | 26.75 | [{"value": 26.75, "product": "CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(C(=O)C=C4)C)OC)CC(F)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | A mixture of 5-(6-amino-2-methoxypyridin-3-yl)-1-methylpyridin-2(1H)-one (0.2 g, 0.86 mmol), 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.243 g, 0.86 mmol), Palladium(II) acetate (0.019 g, 0.09 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.050 g, 0.09 mmol) and... | 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.c1ccncc1 | HCl | CCC(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].C1COCCO1 | 120 | null | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1ccc(=O)n(C)c1>CCC(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].C1COCCO1>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1ccc(=O)n(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d7d32d49e289422b9b8afc82aae7319c | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=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] | 39.87 | [{"value": 39.87, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Pd complexe (147 mg, 0.17 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (600 mg, 1.67 mmol), 1-bromo-3,5-difluorobenzene (0.241 ml, 2.09 mmol) and cesium carbonate (818 mg, 2.51 mmol) dissolved in 1,4-dioxane (12 ml). The resulting suspension was degased... | 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 | 100 | null | COC(=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>COC(=O)c1cc(C2CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f01bb0709ba64daa9f491765ab642ed8 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=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] | 58.12 | [{"value": 58.12, "product": "COC(=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 (33.2 mg, 0.04 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (270 mg, 0.75 mmol), 1-bromo-3,5-difluorobenzene (0.095 ml, 0.83 mmol) and cesium carbonate (368 mg, 1.13 mmol) dissolved in 1,4-dioxane (5 ml). The resulting suspension was degased... | 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 | COC(=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>COC(=O)c1cc(C2CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a83a9a777a784ae7bc91d681e967fa73 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=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] | 41.59 | [{"value": 41.59, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Pd complexe (142 mg, 0.16 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (577 mg, 1.61 mmol), 1-bromo-3,5-difluorobenzene (0.232 ml, 2.01 mmol) and cesium carbonate (787 mg, 2.41 mmol) dissolved in 1,4-dioxane (12 ml). The resulting suspension was degased... | 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 | 100 | null | COC(=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>COC(=O)c1cc(C2CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-731adccc0a564281bbf0c68982fd70e6 | CCOC(=O)c1coc(N)n1.Clc1ccnc(Cl)c1>>CCOC(=O)c1coc(Nc2cc(Cl)ccn2)n1 | C1=CN=C(C=C1Cl)Cl.CCOC(=O)C1=COC(=N1)N>>CCOC(=O)C1=COC(=N1)NC2=NC=CC(=C2)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][o:8][c:9]([NH2:10])[n:18]1.Cl[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][o:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][n:17]2)[n:18]1 | CCOC(=O)c1coc(N)n1.Clc1ccnc(Cl)c1 | CCOC(=O)c1coc(Nc2cc(Cl)ccn2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=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].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#7;a:10]:[c:11](-[NH2;D1;+0:12]):[#8;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#7;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#8;a:13]:[c:14]:1 | 37.02 | [{"value": 37.02, "product": "CCOC(=O)C1=COC(=N1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 2,4-dichloropyridine (148 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol),ethyl 2-aminooxazole-4-carboxylate (156 mg, 1.00 mmol) were added to an oven dried microwave vial, the vial was capped and placed under ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 140 | null | CCOC(=O)c1coc(N)n1.Clc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1coc(Nc2cc(Cl)ccn2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-621d036677ca44618570da1795ad36a5 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 82.41 | [{"value": 82.41, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Charged a standard microwave vial with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.500 g, 2.45 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.611 g, 2.22 mmol), palladium (II) acetate (0.015 g, 0.07 mmol), rac-BINAP (0.069 g, 0.11 mmol), potassium carbon... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-eeeb45fc43db405282b2d52841087c19 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 54.92 | [{"value": 54.92, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (528 mg, 2.58 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (710 mg, 2.58 mmol), Sodium tert-butoxide (373 mg, 3.88 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (113 mg, 0.18 mmol) and Tris(dibenzylideneacetone)dipalla... | 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.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0624d5800c4b4df5ab74722e43784236 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 100.61 | [{"value": 100.61, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Charged a round-bottom flask with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (5.0 g, 24.48 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (6.73 g, 24.48 mmol), palladium (II) acetate (0.165 g, 0.73 mmol), rac-BINAP (0.762 g, 1.22 mmol), potassium carbonate (5... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f324903a1dbf436dad59daccca5918c2 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 97.77 | [{"value": 97.77, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Charged a round-bottom flask with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (7.6 g, 37.21 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (10.22 g, 37.21 mmol), palladium (II) acetate (0.251 g, 1.12 mmol), rac-BINAP (1.159 g, 1.86 mmol), potassium carbonate (... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b30e73dcf3ae428d887dca581acb0b4f | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 101.53 | [{"value": 101.53, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Charged a round-bottom flask with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (4.5 g, 22.03 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (6.05 g, 22.03 mmol), palladium (II) acetate (0.148 g, 0.66 mmol), rac-BINAP (0.686 g, 1.10 mmol), potassium carbonate (4... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3e65988c6a6b45e0aa2eb265462b21a7 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 58.78 | [{"value": 58.78, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.892 g, 4.37 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (1.20 g, 4.37 mmol), Sodium tert-butoxide (0.630 g, 6.55 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.272 g, 0.44 mmol) and Tris(dibenzylideneacetone)dipa... | 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.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d106e5c0510845f092f0e721b9abc1a2 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 86.23 | [{"value": 86.23, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | Charged a round-bottom flask with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.76 g, 3.72 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (1.022 g, 3.72 mmol), palladium (II) acetate (0.025 g, 0.11 mmol), rac-BINAP (0.116 g, 0.19 mmol), potassium carbonate (0... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-570c79ad72a549d498fb0aa790356a1e | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 37.5 | [{"value": 37.5, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | 2011-05-03; 16:30 Charged a round-bottom flask with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (16 g, 78.34 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (21.52 g, 78.34 mmol), palladium (II) acetate (0.528 g, 2.35 mmol), rac-BINAP (2.439 g, 3.92 mmol), pot... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7d5963f655d84875bf61ad4d09b53b49 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 78.24 | [{"value": 78.24, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | To a 250 mL roundbottomed flask was added 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (5.5 g, 23.11 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (6.50 g, 23.11 mmol), Palladium(II)acetate (0.157 g, 0.69 mmol), rac-BINAP (0.734 g, 1.16 mmol), Potassium carbonate (4.79 g, ... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-23ee6c17726e43148570d3de230c90b7 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 67.69 | [{"value": 67.69, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | To a 250 mL roundbottomed flask was added 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (6 g, 25.21 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (7.10 g, 25.21 mmol), Palladium(II)acetate (0.171 g, 0.76 mmol), rac-BINAP (0.801 g, 1.26 mmol), Potassium carbonate (5.23 g, 37... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bea3ac5058c048368377611c2ed94139 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5 | 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-[c:28]1[cH:29][n:30][n: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-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)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] | 32.29 | [{"value": 32.29, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (558 mg, 2.73 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (750 mg, 2.73 mmol), Sodium tert-butoxide (394 mg, 4.09 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (119 mg, 0.19 mmol) and Tris(dibenzylideneacetone)dipalla... | 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.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-23ff93d7067c46afbfd708d8d8da4502 | COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccnc(C2CN(C)Cc3ccc(Cl)nc3O2)c1>>COc1nc(Nc2ccc3c(n2)OC(c2cc(C)ccn2)CN(C)C3)ccc1-c1cnn(C)c1 | CC1=CC(=NC=C1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CC(=NC=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC)C | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:26][cH:27][c:28]1-[c:29]1[cH:30][n:31][n:32]([CH3:33])[cH:34]1.Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[cH:16][c:17]([CH3:18])[cH:19][cH:20][n:21]1)[CH2:22][N:23]([CH3:24])[CH2:25]2>>[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]... | COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccnc(C2CN(C)Cc3ccc(Cl)nc3O2)c1 | COc1nc(Nc2ccc3c(n2)OC(c2cc(C)ccn2)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)cn4)nc3O2)nc1 | 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] | 43.12 | [{"value": 43.12, "product": "CC1=CC(=NC=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (66.3 mg, 0.32 mmol), 8-chloro-4-methyl-2-(4-methylpyridin-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (94 mg, 0.32 mmol), Sodium tert-butoxide (46.8 mg, 0.49 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (20.20 mg, 0.03 mmol) and Tris(dibenzylidene... | 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.c1ccncc1.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccnc(C2CN(C)Cc3ccc(Cl)nc3O2)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>COc1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c9c2650e754c4141a34b6871c226f8e2 | COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccc(C2CN(C)Cc3ccc(Cl)nc3O2)nc1>>COc1nc(Nc2ccc3c(n2)OC(c2ccc(C)cn2)CN(C)C3)ccc1-c1cnn(C)c1 | CC1=CN=C(C=C1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CN=C(C=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC)C | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:26][cH:27][c:28]1-[c:29]1[cH:30][n:31][n:32]([CH3:33])[cH:34]1.Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[cH:16][cH:17][c:18]([CH3:19])[cH:20][n:21]1)[CH2:22][N:23]([CH3:24])[CH2:25]2>>[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]... | COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccc(C2CN(C)Cc3ccc(Cl)nc3O2)nc1 | COc1nc(Nc2ccc3c(n2)OC(c2ccc(C)cn2)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)cn4)nc3O2)nc1 | 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] | 67.71 | [{"value": 67.71, "product": "CC1=CN=C(C=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.112 g, 0.55 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.112 g, 0.55 mmol), Sodium tert-butoxide (0.079 g, 0.82 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.034 g, 0.05 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.025 g, 0... | 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.c1ccncc1.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccc(C2CN(C)Cc3ccc(Cl)nc3O2)nc1>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>COc1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1563c8430590422cb033c9d23b6239c7 | 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.CC(=O)O.CC(=O)O.[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] | 51.21 | [{"value": 51.21, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (2.90 mg, 0.01 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (120 mg, 0.32 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (15.89 mg, 0.03 mmol), 1-bromo-3,5-difluorobenzene (46.5 µl, 0.40 mmol) and cesium carbon... | 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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | 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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-770b2145b34144d1907205e1cdc145c0 | 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.CC(=O)O.CC(=O)O.[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] | 49.29 | [{"value": 49.29, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (2.90 mg, 0.01 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (120 mg, 0.32 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (15.89 mg, 0.03 mmol), 1-bromo-3,5-difluorobenzene (46.5 µl, 0.40 mmol) and cesium carbon... | 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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | 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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-856e3e504ed54d0cb8cb9c559a0474c7 | C1CCNCC1.CCOC(=O)c1ccc(Br)cc1>>CCOC(=O)c1ccc(N2CCCCC2)cc1 | CCOC(=O)C1=CC=C(C=C1)Br.C1CCNCC1>>CCOC(=O)C1=CC=C(C=C1)N2CCCCC2 | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1.Br[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:16][cH:17]1 | C1CCNCC1.CCOC(=O)c1ccc(Br)cc1 | CCOC(=O)c1ccc(N2CCCCC2)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] | C1COCCO1 | 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] | 81.44 | [{"value": 81.44, "product": "CCOC(=O)C1=CC=C(C=C1)N2CCCCC2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | In a 250 mL round-bottomed flask was ethyl 4-bromobenzoate (816 µl, 5 mmol), piperidine (593 µl, 6.00 mmol), and CESIUM CARBONATE (2444 mg, 7.50 mmol) in dioxane (2.36E+04 µl) to give a white suspension. The solution was degassed with N2 (g) for 15 min and then added BINAP (156 mg, 0.25 mmol) and PALLADIUM(II) ACETATE ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | C1CCNCC1.CCOC(=O)c1ccc(Br)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].C1COCCO1>CCOC(=O)c1ccc(N2CCCCC2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b099625680284510ba7d7318538524ab | C1CCNCC1.CC(C)(C)OC(=O)c1ccc(Br)nc1>>CC(C)(C)OC(=O)c1ccc(N2CCCCC2)nc1 | CC(C)(C)OC(=O)C1=CN=C(C=C1)Br.C1CCNCC1>>CC(C)(C)OC(=O)C1=CN=C(C=C1)N2CCCCC2 | [NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1.Br[c:11]1[cH:10][cH:9][c:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:19][n:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[n:18][cH:19]1 | C1CCNCC1.CC(C)(C)OC(=O)c1ccc(Br)nc1 | CC(C)(C)OC(=O)c1ccc(N2CCCCC2)nc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 10c6f9b26f855d26243e4771b69ba961e55fa770e633c60af6779c5e67cf6f43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a: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](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 61.94 | [{"value": 61.94, "product": "CC(C)(C)OC(=O)C1=CN=C(C=C1)N2CCCCC2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | In a 100 mL round-bottomed flask was tert-butyl 6-bromonicotinate (516 mg, 2 mmol), piperidine (237 µl, 2.40 mmol), and CESIUM CARBONATE (977 mg, 3.00 mmol) in dioxane (9763 µl) to give a white suspension. The solution was degassed with N2 (g) fo 20 mins. PALLADIUM(II) ACETATE (22.45 mg, 0.10 mmol) and BINAP (62.3 mg, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccncc1 | c1ccncc1.C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | C1CCNCC1.CC(C)(C)OC(=O)c1ccc(Br)nc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CC(C)(C)OC(=O)c1ccc(N2CCCCC2)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ff0eb93bbb4b45cdb3807c4588dd206f | C1COCCN1.COC(=O)c1cc(Br)cc(C(=O)OC)c1>>COC(=O)c1cc(C(=O)OC)cc(N2CCOCC2)c1 | COC(=O)C1=CC(=CC(=C1)Br)C(=O)OC.C1COCCN1>>COC(=O)C1=CC(=CC(=C1)N2CCOCC2)C(=O)OC | [NH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1.Br[c:13]1[cH:12][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:12][c:13]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20]1 | C1COCCN1.COC(=O)c1cc(Br)cc(C(=O)OC)c1 | COC(=O)c1cc(C(=O)OC)cc(N2CCOCC2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11].[#8:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:15]1-[C:14]-[C:13]-[#8:12]-[C:17]-[C:16]-1):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11] | 78.22 | [{"value": 78.22, "product": "COC(=O)C1=CC(=CC(=C1)N2CCOCC2)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a solution of dimethyl 5-bromoisophthalate (10 g, 36.62 mmol) in toluene (100 mL) where BINAP (2.5 g, 4.01 mmol), morpholine (4.4 g, 50.50 mmol), CESIUM CARBONATE (18 g, 55.25 mmol) and PALLADIUM(II) ACETATE (0.9 g, 4.01 mmol) added. The solution was heated to reflux under inert atm for 14h. The silvent was filtered... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | 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 | C1COCCN1.COC(=O)c1cc(Br)cc(C(=O)OC)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COC(=O)c1cc(C(=O)OC)cc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-822f9545d2954337a3563b98247b8f3b | Brc1cncc(Br)c1.C1COCCN1>>Brc1cncc(N2CCOCC2)c1 | C1=C(C=NC=C1Br)Br.C1COCCN1>>C1COCCN1C2=CC(=CN=C2)Br | Br[c:6]1[cH:5][n:4][cH:3][c:2]([Br:1])[cH:13]1.[NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1>>[Br:1][c:2]1[cH:3][n:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13]1 | Brc1cncc(Br)c1.C1COCCN1 | Brc1cncc(N2CCOCC2)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 | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]2-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-2):[c:6]:1 | 50.17 | [{"value": 50.17, "product": "C1COCCN1C2=CC(=CN=C2)Br", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A mixture of 3,5-dibromopyridine (3.01 mL, 12.66 mmol), morpholine (1.00 g, 11.48 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.210 g, 0.23 mmol), sodium 2-methylpropan-2-olate (1.655 g, 17.22 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.429 g, 0.69 mmol) in degassed toluene (35 mL) was stirred for 16 hou... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1COCCN1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | Brc1cncc(Br)c1.C1COCCN1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Brc1cncc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3d99515de30641289be85a9d48e7a43a | Brc1cncc(Br)c1.CNCCOC>>COCCN(C)c1cncc(Br)c1 | C1=C(C=NC=C1Br)Br.CNCCOC>>CN(CCOC)C1=CC(=CN=C1)Br | Br[c:7]1[cH:8][n:9][cH:10][c:11]([Br:12])[cH:13]1.[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[cH:8][n:9][cH:10][c:11]([Br:12])[cH:13]1 | Brc1cncc(Br)c1.CNCCOC | COCCN(C)c1cncc(Br)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 | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C;D1;H3:10]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C;D1;H3:10])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 67.64 | [{"value": 67.64, "product": "CN(CCOC)C1=CC(=CN=C1)Br", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A mixture of 3,5-dibromopyridine (1.468 mL, 6.17 mmol), 2-methoxy-N- methylethanamine (0.602 mL, 5.61 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.103 g, 0.11 mmol), sodium 2-methylpropan-2-olate (0.809 g, 8.41 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.175 g, 0.28 mmol) in degassed toluene (15 mL) was... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | 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 | 90 | null | Brc1cncc(Br)c1.CNCCOC>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>COCCN(C)c1cncc(Br)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-370d0a5fbe29487785ea2b57f66774a2 | COc1ccnc(Cl)c1.Nc1ccc(S(N)(=O)=O)cc1>>COc1ccnc(Nc2ccc(S(N)(=O)=O)cc2)c1 | COC1=CC(=NC=C1)Cl.C1=CC(=CC=C1N)S(=O)(=O)N>>COC1=CC(=NC=C1)NC2=CC=C(C=C2)S(=O)(=O)N | Cl[c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19]1.[NH2:8][c:9]1[cH:10][cH:11][c:12]([S:13]([NH2:14])(=[O:15])=[O:16])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([S:13]([NH2:14])(=[O:15])=[O:16])[cH:17][cH:18]2)[cH:19]1 | COc1ccnc(Cl)c1.Nc1ccc(S(N)(=O)=O)cc1 | COc1ccnc(Nc2ccc(S(N)(=O)=O)cc2)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] | CN1CCCC1=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccn2)cc1 | 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:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:9] | 0 | [{"value": 0.0, "product": "COC1=CC(=NC=C1)NC2=CC=C(C=C2)S(=O)(=O)N", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | A mixture of 4-aminobenzenesulfonamide (190mg, 1.10 mmol), 2-chloro-4-methoxypyridine (135 mg, 0.94 mmol), diacetoxypalladium (13mg, 0.06 mmol), cesium carbonate (417mg, 1.28 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (50 mg, 0.09 mmol) in NMP (2.0 mL) was heated **in the microwave** for 10 min... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | 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.CC(=O)O.CC(=O)O.[Pd].CN1CCCC1=O | 150 | null | COc1ccnc(Cl)c1.Nc1ccc(S(N)(=O)=O)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CN1CCCC1=O>COc1ccnc(Nc2ccc(S(N)(=O)=O)cc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2f18202487aa4ad2b8bb581b02b238ef | Brc1ccccc1.Nc1ccc(S(N)(=O)=O)cc1>>NS(=O)(=O)c1ccc(Nc2ccccc2)cc1 | C1=CC=C(C=C1)Br.C1=CC(=CC=C1N)S(=O)(=O)N>>C1=CC=C(C=C1)NC2=CC=C(C=C2)S(=O)(=O)N | Br[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:16][cH:17]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | Brc1ccccc1.Nc1ccc(S(N)(=O)=O)cc1 | NS(=O)(=O)c1ccc(Nc2ccccc2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | 30 | [{"value": 30.0, "product": "C1=CC=C(C=C1)NC2=CC=C(C=C2)S(=O)(=O)N", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | A mixture of 4-aminobenzenesulfonamide (100 mg, 0.58 mmol), bromobenzene (0.061 mL, 0.58 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.9 mg, 0.05 mmol), diacetoxypalladium (5.21 mg, 0.02 mmol) and cesium carbonate (227 mg, 0.70 mmol) in degassed DMA (1.8 mL) was heated **_in the microwave_** for 2... | 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+].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].CC(=O)N(C)C | 130 | null | Brc1ccccc1.Nc1ccc(S(N)(=O)=O)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>NS(=O)(=O)c1ccc(Nc2ccccc2)cc1 |
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