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-3016ae12f45142f49e43a15eaa293eb1 | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Clc1ccccn1>>CC(C)(C)OC(=O)N1CCC[C@@H](Nc2ccccn2)C1 | C1=CC=NC(=C1)Cl.CC(C)(C)OC(=O)N1CCC[C@H](C1)N>>CC(C)(C)OC(=O)N1CCC[C@H](C1)NC2=CC=CC=N2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH2:13])[CH2:20]1.Cl[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][n:19]2)[CH2:20]1 | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Clc1ccccn1 | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2ccccn2)C1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(N[C@@H]2CCCNC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:10] | 93.42 | [{"value": 93.42, "product": "CC(C)(C)OC(=O)N1CCC[C@H](C1)NC2=CC=CC=N2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | Vial 1) Pd2(dba)3 (0.018 g, 0.02 mmol) and BINAP (0.024 g, 0.04 mmol) were mixed in toluene (1mL) under N2 and stirred at rt for 5min. Vial 2) sodium tert-butoxide (0.999 g, 10.08 mmol), tert-butyl (R)-3-aminopiperidine-1-carboxylate (1.249 g, 6.05 mmol) and 2-chloropyridine (0.477 mL, 5.04 mmol) were mixed in tolue... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | 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 | 110 | null | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.Clc1ccccn1>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>CC(C)(C)OC(=O)N1CCC[C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-42c0acd76af041bb93244dbfe53a7422 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccncc1>>c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CN=CC=C1CN>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=NC=C3 | Cl[c:8]1[cH:7][c:6]([NH:5][c:4]2[cH:3][cH:2][cH:1][cH:21][cH:20]2)[n:19][cH:18][cH:17]1.[NH2:9][CH2:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[cH:17][cH:18][n:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccncc1 | c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 29.48 | [{"value": 29.48, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=NC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Pyridin-4-ylmethanamine (58.1 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccncc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccncc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-63fc87ded08344459c39e54d90416da8 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccncc1>>c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CN=CC=C1CN>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=NC=C3 | Cl[c:8]1[cH:7][c:6]([NH:5][c:4]2[cH:3][cH:2][cH:1][cH:21][cH:20]2)[n:19][cH:18][cH:17]1.[NH2:9][CH2:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[cH:17][cH:18][n:19]2)[cH:20][cH:21]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccncc1 | c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 23.11 | [{"value": 23.11, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=NC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Pyridin-4-ylmethanamine (58.1 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccncc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccncc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>c1ccc(Nc2cc(NCc3ccncc3)ccn2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-14a2a1784ff04475ad4db1893eca50ce | CC(C)(C)OC(=O)NC1CCNCC1.O=[N+]([O-])c1cccc(Br)c1>>CC(C)(C)OC(=O)NC1CCN(c2cccc([N+](=O)[O-])c2)CC1 | C1=CC(=CC(=C1)Br)[N+](=O)[O-].CC(C)(C)OC(=O)NC1CCNCC1>>CC(C)(C)OC(=O)NC1CCN(CC1)C2=CC(=CC=C2)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:22][CH2:23]1.Br[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:... | CC(C)(C)OC(=O)NC1CCNCC1.O=[N+]([O-])c1cccc(Br)c1 | CC(C)(C)OC(=O)NC1CCN(c2cccc([N+](=O)[O-])c2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | 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] | 56.63 | [{"value": 56.63, "product": "CC(C)(C)OC(=O)NC1CCN(CC1)C2=CC(=CC=C2)[N+](=O)[O-]", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | A 100 mL round bottom flask was charged with a magnetic stir bar, 1-bromo-3-nitrobenzene (1.000 g, 4.95 mmol), [Reactants], Pd2dba3 (0.227 g, 0.25 mmol), BINAP (0.308 g, 0.50 mmol), Cs2CO3 (4.03 g, 12.38 mmol), and toluene (19.80 ml). The vessel was capped with a septum, placed under an atmosphere of argon, and placed ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 95 | null | CC(C)(C)OC(=O)NC1CCNCC1.O=[N+]([O-])c1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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>CC(C)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ea023f46022d4035acdf5a18572a2571 | CC(=O)OCc1cccc2c(=O)cc(-c3ccc(Br)cc3)oc12.C[C@@H]1CNCCN1>>C[C@@H]1CN(c2ccc(-c3cc(=O)c4cccc(CO)c4o3)cc2)CCN1 | CC(=O)OCC1=C2C(=CC=C1)C(=O)C=C(O2)C3=CC=C(C=C3)Br.C[C@@H]1CNCCN1>>C[C@@H]1CN(CCN1)C2=CC=C(C=C2)C3=CC(=O)C4=CC=CC(=C4O3)CO | CC(=O)[O:19][CH2:18][c:17]1[cH:16][cH:15][cH:14][c:13]2[c:11](=[O:12])[cH:10][c:9](-[c:8]3[cH:7][cH:6][c:5](Br)[cH:23][cH:22]3)[o:21][c:20]21.[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:24][CH2:25][NH:26]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][c:11](=[O:12])[c:13]4[cH:14][cH:15][cH:16][c:17]([CH2:1... | CC(=O)OCc1cccc2c(=O)cc(-c3ccc(Br)cc3)oc12.C[C@@H]1CNCCN1 | C[C@@H]1CN(c2ccc(-c3cc(=O)c4cccc(CO)c4o3)cc2)CCN1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | c0e52c2054586374a0ec83b12a8d1fbf3644327ae752308fa666bb0a37ca1727 | 04c8bc1692f639277efb6482bc7a83b4782a3627dd0e275905c2bfb0e638743d | O=c1cc(-c2ccc(N3CCNCC3)cc2)oc2ccccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(=O)-[O;H0;D2;+0:6]-[C:7]-[c:8]:[c:9]:[#8;a:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8;a:10]:[c:9]:[c:8]-[C:7]-[OH;D1;+0:6].[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1):[c:4]:[c:5] | 13.31 | [{"value": 13.31, "product": "C[C@@H]1CN(CCN1)C2=CC=C(C=C2)C3=CC(=O)C4=CC=CC(=C4O3)CO", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | diacetoxypalladium (6.02 mg, 0.03 mmol) was added to a degassed mixture of (2-(4-bromophenyl)-4-oxo-4H-chromen-8-yl)methyl acetate (200 mg, 0.54 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (25.03 mg, 0.04 mmol) and cesium carbonate (244 mg, 0.75 mmol) in toluene (5 mL). The resulting suspension was stirred at... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Ester.Secondary amine | Primary alcohol.Tertiary amine | c1ccccc1.C1CNCCN1 | C1CNCC[NH]1.c1ccccc1 | C1CNCC[NH]1.c1ccccc1.c1ccc2ccccc2o1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | CC(=O)OCc1cccc2c(=O)cc(-c3ccc(Br)cc3)oc12.C[C@@H]1CNCCN1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>C[C@@H]1CN(c2ccc(-c3cc(=O)c4cccc(CO)c4o3)cc2)CCN1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-71ad501d78264f9aa8b8fb6c66e7e044 | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)c(F)cc1C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=CC(=C(C=C1NC(=O)C)N)F>>CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)F | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:24]([F:25])[cH:26][c:27]1[CH3:28].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]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]3[n:17][cH... | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)c(F)cc1C | 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 | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 20.63 | [{"value": 20.63, "product": "CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In 20 ml microwave vial were added 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (200 mg, 0.86 mmol), N-(5-amino-4-fluoro-2-methylphenyl)acetamide (164 mg, 0.90 mmol), Pd2dba3 (39.2 mg, 0.04 mmol), di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (37.5 mg, 0.09 mmol) and Cs2CO3 (837 m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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 | 150 | null | CC(=O)Nc1cc(N)c(F)cc1C.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].C1COCCO1>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0fa3456b7ef04add84c9ed9afa8e014e | C1COCCN1.CCOC(=O)c1cccc(Br)c1>>CCOC(=O)c1cccc(N2CCOCC2)c1 | CCOC(=O)C1=CC(=CC=C1)Br.C1COCCN1>>CCOC(=O)C1=CC(=CC=C1)N2CCOCC2 | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.Br[c:10]1[cH:9][cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[cH:17]1 | C1COCCN1.CCOC(=O)c1cccc(Br)c1 | CCOC(=O)c1cccc(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].[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-1):[c:7]:[c:8] | 79.84 | [{"value": 79.84, "product": "CCOC(=O)C1=CC(=CC=C1)N2CCOCC2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A mixture of ethyl 3-bromobenzoate (0.070 mL, 0.44 mmol), cesium carbonate (427 mg, 1.31 mmol), diacetoxypalladium (4.90 mg, 0.02 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (5.44 mg, 8.73 µmol) and morpholine (0.042 mL, 0.48 mmol) in toluene (2 mL) was refluxed for 1h. The reaction mixture was cooled and filter... | 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.CCOC(=O)c1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CCOC(=O)c1cccc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c9d3e32c4ae3434fab0938e5982b9ebd | Brc1cccnc1.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(c2cccnc2)CC1 | C1=CC(=CN=C1)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC=C2 | Br[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:18][CH2:19]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][n:16][cH:17]2)[CH2:18][CH2:19]1 | Brc1cccnc1.CC(C)(C)OC(=O)N1CCNCC1 | CC(C)(C)OC(=O)N1CCN(c2cccnc2)CC1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | 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 | 37.96 | [{"value": 37.96, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.072 g, 0.32 mmol) and RuPhos (0.301 g, 0.64 mmol) were stirred in 1,4-dioxane (11.36 ml) for 10 mins at 50 °C.tert-butyl piperazine-1-carboxylate (0.6 g, 3.22 mmol), 3-bromopyridine (0.310 ml, 3.22 mmol) and sodium tert-butoxide (0.464 g, 4.83 mmol) were added and the reaction mixture was stirred ... | 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+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Brc1cccnc1.CC(C)(C)OC(=O)N1CCNCC1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CC(C)(C)OC(=O)N1CCN(c2cccnc2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7977e1a392644e76ab21a7fab838843f | Brc1cccnc1.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(c2cccnc2)CC1 | C1=CC(=CN=C1)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC=C2 | Br[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:18][CH2:19]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][n:16][cH:17]2)[CH2:18][CH2:19]1 | Brc1cccnc1.CC(C)(C)OC(=O)N1CCNCC1 | CC(C)(C)OC(=O)N1CCN(c2cccnc2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 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 | 29.23 | [{"value": 29.23, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC=C2", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.059 g, 0.06 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.080 g, 0.13 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (31.6 ml) was added and the resulting mixture heated to 90°C for 10 minutes then cooled to room temperature. ... | 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+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 85 | null | Brc1cccnc1.CC(C)(C)OC(=O)N1CCNCC1>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>CC(C)(C)OC(=O)N1CCN(c2cccnc2)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b4111a9cc1ab4be8bf9e586d821e9697 | Brc1ccccc1.Nc1cccc(CO)c1>>OCc1cccc(Nc2ccccc2)c1 | C1=CC=C(C=C1)Br.C1=CC(=CC(=C1)N)CO>>C1=CC=C(C=C1)NC2=CC=CC(=C2)CO | Br[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1 | Brc1ccccc1.Nc1cccc(CO)c1 | OCc1cccc(Nc2ccccc2)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] | C1CCOC1 | 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] | 11.13 | [{"value": 11.13, "product": "C1=CC=C(C=C1)NC2=CC=CC(=C2)CO", "details": "", "is_desired": true}] | 65 | CELSIUS | null | null | A solution of Tris(dibenzylideneacetone)dipalladium(0) (0.178 g, 0.19 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol) in THF (20 mL) (degassed) was heated to 50 ºC under a nitrogen atmosphere for 30 min. (3-(phenylamino)phenyl)methanol (0.072 g, 11.13 %) (0.4 g, 3.25 mmol) and ... | 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.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1 | 65 | null | Brc1ccccc1.Nc1cccc(CO)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].C1CCOC1>OCc1cccc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-971b196dec9043e8982df95c855b9cba | COc1nc(N)ncc1Br.FC(F)(F)c1cccc(I)c1>>COc1nc(Nc2cccc(C(F)(F)F)c2)ncc1Br | C1=CC(=CC(=C1)I)C(F)(F)F.COC1=NC(=NC=C1Br)N>>COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:17][cH:18][c:19]1[Br:20].I[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[n:17][cH:18][c:19]1[Br:20] | COc1nc(N)ncc1Br.FC(F)(F)c1cccc(I)c1 | COc1nc(Nc2cccc(C(F)(F)F)c2)ncc1Br | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]):[c:4]:[c:5] | 8.77 | [{"value": 8.77, "product": "COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | _EN06995-11\Reaction_ and many others **_Aim:-_ prepare target for further use.** 1-iodo-3-(trifluoromethyl)benzene (0.215 ml, 1.49 mmol), 5-bromo-4-methoxypyrimidin-2-amine (0.254 g, 1.24 mmol), PALLADIUM(II) ACETATE (0.014 g, 0.06 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (0.054 g, 0.09 mmol) and c... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1cncnc1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | COc1nc(N)ncc1Br.FC(F)(F)c1cccc(I)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>COc1nc(Nc2cccc(C(F)(F)F)c2)ncc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e759a68ff56d4b3bb4604b0f87a340c5 | C1CCNCC1.COc1ccc(N2CCN(C)CC2)c2c1CCN(C(=O)Cc1ccc(Br)cc1)C2>>COc1ccc(N2CCN(C)CC2)c2c1CCN(C(=O)Cc1ccc(N3CCCCC3)cc1)C2 | CN1CCN(CC1)C2=C3CN(CCC3=C(C=C2)OC)C(=O)CC4=CC=C(C=C4)Br.C1CCNCC1>>CN1CCN(CC1)C2=C3CN(CCC3=C(C=C2)OC)C(=O)CC4=CC=C(C=C4)N5CCCCC5 | [NH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1.Br[c:25]1[cH:24][cH:23][c:22]([CH2:21][C:19]([N:18]2[CH2:17][CH2:16][c:15]3[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([N:7]4[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]4)[c:14]3[CH2:34]2)=[O:20])[cH:33][cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]... | C1CCNCC1.COc1ccc(N2CCN(C)CC2)c2c1CCN(C(=O)Cc1ccc(Br)cc1)C2 | COc1ccc(N2CCN(C)CC2)c2c1CCN(C(=O)Cc1ccc(N3CCCCC3)cc1)C2 | 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] | COCCOC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(Cc1ccc(N2CCCCC2)cc1)N1CCc2cccc(N3CCNCC3)c2C1 | 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] | 0 | [{"value": 0.0, "product": "CN1CCN(CC1)C2=C3CN(CCC3=C(C=C2)OC)C(=O)CC4=CC=C(C=C4)N5CCCCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-(4-bromophenyl)-1-(5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (125 mg, 0.27 mmol),[Reactants],piperidine (23.22 mg, 0.27 mmol) was taken in a mixture of DME (5 mL):water (1.250 mL) under N2.The reaction mixture was purged under N2 for 10 min.Tris(dibenzylideneacetone)dipalladium (0)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | C1C[NH]CC[NH]1.c1ccc2c(c1)CC[NH]C2.c1ccccc1.C1CC[NH]CC1 | 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].COCCOC | 100 | null | C1CCNCC1.COc1ccc(N2CCN(C)CC2)c2c1CCN(C(=O)Cc1ccc(Br)cc1)C2>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].COCCOC>COc1ccc(N2CCN(C)CC2)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d99eea842421462c960430aa6c192254 | Clc1cnnc2ccccc12.Cn1ncc(C(=O)N2CCC(N)CC2)c1Cl>>Cn1ncc(C(=O)N2CCC(Nc3cnnc4ccccc34)CC2)c1Cl | C1=CC=C2C(=C1)C(=CN=N2)Cl.CN1C(=C(C=N1)C(=O)N2CCC(CC2)N)Cl>>CN1C(=C(C=N1)C(=O)N2CCC(CC2)NC3=CN=NC4=CC=CC=C43)Cl | Cl[c:13]1[cH:14][n:15][n:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.[CH3:1][n:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][CH:11]([NH2:12])[CH2:23][CH2:24]2)[c:25]1[Cl:26]>>[CH3:1][n:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][CH:11]([NH:12][c:13]3[cH:14][n:15][n:16][c:17]4[cH:18][cH:19][cH:20]... | Clc1cnnc2ccccc12.Cn1ncc(C(=O)N2CCC(N)CC2)c1Cl | Cn1ncc(C(=O)N2CCC(Nc3cnnc4ccccc34)CC2)c1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 8348860e85d70e5332f2c96f54862e4aed219e4a24bead3b76a8c3710c80b718 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1cn[nH]c1)N1CCC(Nc2cnnc3ccccc23)CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[C:12] | 8.14 | [{"value": 8.14, "product": "CN1C(=C(C=N1)C(=O)N2CCC(CC2)NC3=CN=NC4=CC=CC=C43)Cl", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | (4-aminopiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone (442 mg, 1.82 mmol) was taken in a microwave tube. Added racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (113 mg, 0.18 mmol) followed by the addition of Palladium (II) acetate (40.9 mg, 0.18 mmol), racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthy... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2nnccc2c1 | c1ccc2nnccc2c1 | c1c[nH]nc1.C1CC[NH]CC1.c1ccc2nnccc2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 140 | null | Clc1cnnc2ccccc12.Cn1ncc(C(=O)N2CCC(N)CC2)c1Cl>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Cn1ncc(C(=O)N2CCC(Nc3cnnc4ccccc34)CC2)c1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-322a5f0c927a43d5b08115d8443f975d | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)ccc1-n1cnc(C)c1 | CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC.Cl>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C)OC | 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][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[C:24]2=[O:25].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:26][cH:27][c:28]1-[n:29]1[cH:30][n:31][c:32]([CH3:33])[cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2... | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCC(c2ccccc2)Oc2nc(Nc3ccc(-n4ccnc4)cc3)ccc21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 40.02 | [{"value": 40.02, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | were placed in a microwave vial equipped with a stirring bar. The vial was capped and flushed with argon. DME (2 mL) and Et3N (0.028 mL, 0.20 mmol) were added via a syringe and the mixture was stirred at room temperature for 30 min and then heated to 100°C in a microwave apparatus for 1h. The reaction mixture was dilut... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5410161a80384996abaacdd18920aec7 | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCN(C)C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N(C)CCN(C)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]([CH3:28])[CH2:29][CH2:30][N:31]([CH3:32])[CH3:33].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]([NH:12][... | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCN(C)C | 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 | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 15.62 | [{"value": 15.62, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | Two reactions setup, each 600 mg scale. A 20 mL microwave reactor vial was charged with 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (1.2 g, 5.14 mmol), N-(5-amino-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acetamide (1.414 g, 5.65 mmol), 2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-b... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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 | 150 | null | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.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].C1COCCO1>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c4c5eb3c12504ceeb83c5886c7e20d94 | Brc1ccc2nccn2c1.C1COCCN1>>c1cn2cc(N3CCOCC3)ccc2n1 | C1=CC2=NC=CN2C=C1Br.C1COCCN1>>C1COCCN1C2=CN3C=CN=C3C=C2 | Br[c:5]1[cH:4][n:3]2[cH:2][cH:1][n:15][c:14]2[cH:13][cH:12]1.[NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>>[cH:1]1[cH:2][n:3]2[cH:4][c:5]([N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)[cH:12][cH:13][c:14]2[n:15]1 | Brc1ccc2nccn2c1.C1COCCN1 | c1cn2cc(N3CCOCC3)ccc2n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.Cl[Pd+].C1=CC=C(C=C1)C2=CC=CC=C2N | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | c54bda83f134b647d59d37e2ce5b5c25dc08d24978359a85e9030bed4e139a25 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cn2cc(N3CCOCC3)ccc2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:2:[c:9]:1.[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]2:[c:9]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]3-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-3):[c:2]:[c:3]:[c:4]:1:2 | 31.84 | [{"value": 31.84, "product": "C1COCCN1C2=CN3C=CN=C3C=C2", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 6-bromoimidazo[1,2-a]pyridine (299 mg, 1.52 mmol), dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (35.4 mg, 0.08 mmol), RuPhos 2nd generation (58.9 mg, 0.08 mmol), morpholine (0.159 ml, 1.82 mmol) and cesium carbonate (1483 mg, 4.55 mmol) were dissolved in degassed 1,4-dioxane (15.100 ml). Reaction mixt... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccn2ccnc2c1.C1COCCN1 | c1ccn2ccnc2c1.C1COCC[NH]1 | c1ccn2ccnc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.Cl[Pd+].C1=CC=C(C=C1)C2=CC=CC=C2N.C1COCCO1 | 90 | null | Brc1ccc2nccn2c1.C1COCCN1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.Cl[Pd+].C1=CC=C(C=C1)C2=CC=CC=C2N.C1COCCO1>c1cn2cc(N3CCOCC3)ccc2n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-273601a9c88f40afa5574d06d820673e | Cc1cccnc1Br.NC1CCCCC1>>Cc1cccnc1NC1CCCCC1 | CC1=C(N=CC=C1)Br.C1CCC(CC1)N>>CC1=C(N=CC=C1)NC2CCCCC2 | Br[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]1.[NH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1 | Cc1cccnc1Br.NC1CCCCC1 | Cc1cccnc1NC1CCCCC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCCCC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6])-[C:10] | 61.83 | [{"value": 61.83, "product": "CC1=C(N=CC=C1)NC2CCCCC2", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | Ref: EN07957-77 BIS(DIBENZYLIDENEACETONE)PALLADIUM(Pd2((dba)3) (0.101 g, 0.11 mmol) and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.136 g, 0.22 mmol) was was stirred in toluene (16.5 mL) under N2. Then 2-bromo-3-methylpyridine (1.619 mL, 14.53 mmol), cyclohexanamine (1.662 mL, 14.53 mmol) and sodium 2-... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 115 | null | Cc1cccnc1Br.NC1CCCCC1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1cccnc1NC1CCCCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9faf2ea031204c63b2d52d8ff6231013 | Brc1ccccc1.c1ccc(C2CCCN2)cc1>>c1ccc(C2CCCN2c2ccccc2)cc1 | C1=CC=C(C=C1)Br.C1CC(NC1)C2=CC=CC=C2>>C1CC(N(C1)C2=CC=CC=C2)C3=CC=CC=C3 | Br[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8][NH:9]2)[cH:16][cH:17]1>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8][N:9]2[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | Brc1ccccc1.c1ccc(C2CCCN2)cc1 | c1ccc(C2CCCN2c2ccccc2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(C2CCCN2c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[c:6]-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:7]-1-[c:6]):[c:4]:[c:5] | 90.18 | [{"value": 90.18, "product": "C1CC(N(C1)C2=CC=CC=C2)C3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Caesium carbonate (553 mg, 1.70 mmol) was added to bromobenzene (0.059 mL, 0.57 mmol) and 2-phenylpyrrolidine (100 mg, 0.68 mmol) in 1,4-dioxane (2 mL). The reaction was degassed and Tris(dibenzylideneacetone)?dipalladium(0) (12.96 mg, 0.01 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (RuPho... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | C1CC[NH]C1.c1ccccc1 | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | Brc1ccccc1.c1ccc(C2CCCN2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>c1ccc(C2CCCN2c2ccccc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f61e41a27de94fdca6031e20c1049254 | Cc1csc(Cl)n1.NCc1ccccc1>>Cc1csc(NCc2ccccc2)n1 | CC1=CSC(=N1)Cl.C1=CC=C(C=C1)CN>>CC1=CSC(=N1)NCC2=CC=CC=C2 | Cl[c:5]1[s:4][cH:3][c:2]([CH3:1])[n:14]1.[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14]1 | Cc1csc(Cl)n1.NCc1ccccc1 | Cc1csc(NCc2ccccc2)n1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 8de8ca2517a540af5504af5f928939db3734aebd9b72e44df71c2713b5eb2f08 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2nccs2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 0 | [{"value": 0.0, "product": "CC1=CSC(=N1)NCC2=CC=CC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | phenylmethanamine (100 mg, 0.93 mmol), 2-chloro-4-methylthiazole (125 mg, 0.93 mmol) and sodium 2-methylpropan-2-olate (179 mg, 1.87 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ET... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cscn1 | c1cscn1 | c1cscn1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Cc1csc(Cl)n1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Cc1csc(NCc2ccccc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-18cf4521e927457b894e96f153aedd6a | CCOC(=O)c1cnc(N)o1.FC(F)(F)c1ccc(Cl)nc1>>CCOC(=O)c1cnc(Nc2ccc(C(F)(F)F)cn2)o1 | C1=CC(=NC=C1C(F)(F)F)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=C(C=C2)C(F)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:21]1.Cl[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][n:20]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][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][n:20]2)[o:21]1 | CCOC(=O)c1cnc(N)o1.FC(F)(F)c1ccc(Cl)nc1 | CCOC(=O)c1cnc(Nc2ccc(C(F)(F)F)cn2)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 | 61.47 | [{"value": 61.47, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=C(C=C2)C(F)(F)F", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Test of scope in the coupling of ester substituted aminooxazole To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), 2-chloro-5-(trifluoromethyl)pyridine (181 mg, 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+].CC1(C2=C(C(=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.FC(F)(F)c1ccc(Cl)nc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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(Nc2ccc(C(F)(F)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-dfbe9b6e6d2042eaacda8fae236486c2 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1F>>Fc1ccccc1CNc1ccnc(Nc2ccccc2)c1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC=C(C(=C1)CN)F>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=CC=C3F | Cl[c:10]1[cH:11][cH:12][n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1.[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9]>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][c:10]1[cH:11][cH:12][n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1F | Fc1ccccc1CNc1ccnc(Nc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 62.09 | [{"value": 62.09, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=CC=C3F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (2-fluorophenyl)methanamine (67.3 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSP... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1ccccc1F>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Fc1ccccc1CNc1ccnc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-771383a2857c4cf6924928bdcc9bb648 | COc1nc(N)ccc1-n1cnc(C)c1.Cc1cnc(C2CN(C)Cc3ccc(Cl)nc3O2)s1>>COc1nc(Nc2ccc3c(n2)OC(c2ncc(C)s2)CN(C)C3)ccc1-n1cnc(C)c1 | CC1=CN=C(S1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C.CC1=CN(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CN=C(S1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)N5C=C(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-[n:28]1[cH:29][n:30][c: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][cH:17][c:18]([CH3:19])[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-n1cnc(C)c1.Cc1cnc(C2CN(C)Cc3ccc(Cl)nc3O2)s1 | COc1nc(Nc2ccc3c(n2)OC(c2ncc(C)s2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OC(c3nccs3)CNC4)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] | 73.84 | [{"value": 73.84, "product": "CC1=CN=C(S1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)N5C=C(N=C5)C)OC)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-4-methyl-2-(5-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (140 mg, 0.47 mmol), 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (106 mg, 0.52 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (16.59 mg, 0.05 mmol), PALLADIUM(II) ACETATE (10.63 mg, 0.05 mmol) and Cs2CO3 (308 mg, 0.95 mmol) we... | 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.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | COc1nc(N)ccc1-n1cnc(C)c1.Cc1cnc(C2CN(C)Cc3ccc(Cl)nc3O2)s1>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(c2ncc(C)s2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bb9134ed03e248f6b9498f9cb351f5cb | Clc1cccnc1Cl.NC(=O)c1ccccc1>>O=C(Nc1ncccc1Cl)c1ccccc1 | C1=CC(=C(N=C1)Cl)Cl.C1=CC=C(C=C1)C(=O)N>>C1=CC=C(C=C1)C(=O)NC2=C(C=CC=N2)Cl | Cl[c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[Cl:10].[O:1]=[C:2]([NH2:3])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[Cl:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | Clc1cccnc1Cl.NC(=O)c1ccccc1 | O=C(Nc1ncccc1Cl)c1ccccc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=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 | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1ccccn1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]):[#7;a:2]:[c:3] | 10.78 | [{"value": 10.78, "product": "C1=CC=C(C=C1)C(=O)NC2=C(C=CC=N2)Cl", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | In a 5 mL vial were added Pd(OAc)2 (6.85 mg, 0.03 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (35.3 mg, 0.06 mmol), N-(3-chloropyridin-2-yl)benzamide (15.30 mg, 10.78 %) and cesium carbonate (477 mg, 1.46 mmol) in dioxane (2 mL) to give a yellow solution. The flask was evacuated and filled with Nit... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | 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].C1COCCO1 | 110 | null | Clc1cccnc1Cl.NC(=O)c1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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=C(Nc1ncccc1Cl)c1ccccc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1d6228eeae6e455c9c2acbb4c4aa8214 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1ccnc(Cl)c1>>CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2c1cc(C(F)(F)F)ccn1 | C1=CN=C(C=C1C(F)(F)F)Cl.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][NH:14]2.Cl[c:15]1[cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23][n:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][N:14]2[c:15]1[cH:16][c:17]([C:18]([F:19])([... | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1ccnc(Cl)c1 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2c1cc(C(F)(F)F)ccn1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 283b1960c227387bf15bed917434ac19c87410d6f8e202e473586b792b097580 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2C[C@@H]3C[C@H]2CN3)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]2-[C:9]-[C:10]-1-[C:11]-[NH;D2;+0:12]-2>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]2-[#7:6]-[C:7]-[C:8]-1-[C:9]-2):[#7;a:2]:[c:3] | 73.34 | [{"value": 73.34, "product": "CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | A 2.0-5.0 mL microwave vial was charged with (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (200 mg, 1.01 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (62.8 mg, 0.10 mmol), Sodium tert-butoxide (116 mg, 1.21 mmol), 2-Chloro-4-(trifluoromethyl)pyridine (0.156 mL, 1.21 mmol) and a mixture of to... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1[NH][C@@H]2CN[C@H]1C2.c1ccncc1 | C1[NH][C@@H]2C[NH][C@H]1C2.c1ccncc1 | C1[NH][C@@H]2C[NH][C@H]1C2.c1ccncc1 | 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 | 105 | null | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1ccnc(Cl)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-34df93999d2b40d3bb96c4985f9877e7 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1ccnc(Cl)c1>>CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2c1cc(C(F)(F)F)ccn1 | C1=CN=C(C=C1C(F)(F)F)Cl.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][NH:14]2.Cl[c:15]1[cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23][n:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][N:14]2[c:15]1[cH:16][c:17]([C:18]([F:19])([... | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1ccnc(Cl)c1 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2c1cc(C(F)(F)F)ccn1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 283b1960c227387bf15bed917434ac19c87410d6f8e202e473586b792b097580 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2C[C@@H]3C[C@H]2CN3)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]2-[C:9]-[C:10]-1-[C:11]-[NH;D2;+0:12]-2>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]2-[#7:6]-[C:7]-[C:8]-1-[C:9]-2):[#7;a:2]:[c:3] | 33.88 | [{"value": 33.88, "product": "CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | A 2.0-5.0 mL microwave vial was charged with (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (150 mg, 0.76 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (47.1 mg, 0.08 mmol), Sodium tert-butoxide (87 mg, 0.91 mmol), 2-Chloro-4-(trifluoromethyl)pyridine (0.117 mL, 0.91 mmol) and and mixture of t... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1[NH][C@@H]2CN[C@H]1C2.c1ccncc1 | C1[NH][C@@H]2C[NH][C@H]1C2.c1ccncc1 | C1[NH][C@@H]2C[NH][C@H]1C2.c1ccncc1 | 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 | 120 | null | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1ccnc(Cl)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-66ec8d5c98634ce5baad8122520ec3b5 | CN1CC(N)CCC1=O.Clc1cccnc1Br>>CN1CC(Nc2ncccc2Cl)CCC1=O | C1=CC(=C(N=C1)Br)Cl.CN1CC(CCC1=O)N>>CN1CC(CCC1=O)NC2=C(C=CC=N2)Cl | [CH3:1][N:2]1[CH2:3][CH:4]([NH2:5])[CH2:13][CH2:14][C:15]1=[O:16].Br[c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[CH3:1][N:2]1[CH2:3][CH:4]([NH:5][c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[Cl:12])[CH2:13][CH2:14][C:15]1=[O:16] | CN1CC(N)CCC1=O.Clc1cccnc1Br | CN1CC(Nc2ncccc2Cl)CCC1=O | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CCC(Nc2ccccn2)CN1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#7:7]-[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[#7:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6])-[C:11] | 0 | [{"value": 0.0, "product": "CN1CC(CCC1=O)NC2=C(C=CC=N2)Cl", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | In a 10 ml MW vial, Pd2((dba)3 (10.85 mg, 0.01 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (14.56 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (261 mg, 2.71 mmol), 5-amino-1-methylpiperidin-2-one (200 mg, 1.56 mmol) and 2-bromo-3-chloropyridine (300 mg, 1.56 mmol) mixed in toluene (3 mL) to give a b... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 115 | null | CN1CC(N)CCC1=O.Clc1cccnc1Br>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>CN1CC(Nc2ncccc2Cl)CCC1=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-85488250153944e595f74578eeba1555 | Cc1ccc([N+](=O)[O-])cc1Br.NC1COC1>>Cc1ccc([N+](=O)[O-])cc1NC1COC1 | CC1=C(C=C(C=C1)[N+](=O)[O-])Br.C1C(CO1)N.Cl>>CC1=C(C=C(C=C1)[N+](=O)[O-])NC2COC2 | Br[c:10]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9]1.[NH2:11][CH:12]1[CH2:13][O:14][CH2:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH:11][CH:12]1[CH2:13][O:14][CH2:15]1 | Cc1ccc([N+](=O)[O-])cc1Br.NC1COC1 | Cc1ccc([N+](=O)[O-])cc1NC1COC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2COC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[NH2;D1;+0:7]-[C:8]1-[C:9]-[#8:10]-[C:11]-1>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]1-[C:9]-[#8:10]-[C:11]-1):[c:2]:[c:3] | 28.82 | [{"value": 28.82, "product": "CC1=C(C=C(C=C1)[N+](=O)[O-])NC2COC2", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-bromo-1-methyl-4-nitrobenzene (864 mg, 4mmol), oxetan-3-amine hydrochloride (438 mg, 4 mmol), CS2CO3 (3910 mg, 12.00 mmol), palladium(II) acetate (44.9 mg, 0.20 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t- butylphosphine (224 mg, 0.40 mmol) in 1,4-doxane was degased, inflated with Ar and heate... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | 90 | null | Cc1ccc([N+](=O)[O-])cc1Br.NC1COC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd]>Cc1ccc([N+](=O)[O-])cc1NC1COC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2c0a8dbc66b74712a354b7c2ed2d9d4c | Fc1ccc(Nc2cc(Cl)ccn2)cc1.NCc1ccccc1>>Fc1ccc(Nc2cc(NCc3ccccc3)ccn2)cc1 | C1=CC(=CC=C1NC2=NC=CC(=C2)Cl)F.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=C(C=C3)F | Cl[c:9]1[cH:8][c:7]([NH:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:22][cH:21]2)[n:20][cH:19][cH:18]1.[NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][c:9]([NH:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][n:20]2)[cH:21][cH:22]1 | Fc1ccc(Nc2cc(Cl)ccn2)cc1.NCc1ccccc1 | Fc1ccc(Nc2cc(NCc3ccccc3)ccn2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 74.38 | [{"value": 74.38, "product": "C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=C(C=C3)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Phenylmethanamine (52.9 mg, 0.49 mmol), 4-chloro-N-(4-fluorophenyl)pyridin-2-amine (100 mg, 0.45 mmol) and sodium 2-methylpropan-2-olate (86 mg, 0.90 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPH... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Fc1ccc(Nc2cc(Cl)ccn2)cc1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Fc1ccc(Nc2cc(NCc3ccccc3)ccn2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b16c1805f7d5406ba2f0d69bfae1736b | COc1cc(N2CCN(CCO)CC2)ccc1N.Clc1ncc(Cl)c(-c2cnn3ccccc23)n1>>COc1cc(N2CCN(CCO)CC2)ccc1Nc1ncc(Cl)c(-c2cnn3ccccc23)n1 | C1=CC2=C(C=NN2C=C1)C3=NC(=NC=C3Cl)Cl.COC1=C(C=CC(=C1)N2CCN(CC2)CCO)N>>COC1=C(C=CC(=C1)N2CCN(CC2)CCO)NC3=NC=C(C(=N3)C4=C5C=CC=CN5N=C4)Cl | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][OH:12])[CH2:13][CH2:14]2)[cH:15][cH:16][c:17]1[NH2:18].Cl[c:19]1[n:20][cH:21][c:22]([Cl:23])[c:24](-[c:25]2[cH:26][n:27][n:28]3[cH:29][cH:30][cH:31][cH:32][c:33]23)[n:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][O... | COc1cc(N2CCN(CCO)CC2)ccc1N.Clc1ncc(Cl)c(-c2cnn3ccccc23)n1 | COc1cc(N2CCN(CCO)CC2)ccc1Nc1ncc(Cl)c(-c2cnn3ccccc23)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccn2ncc(-c3ccnc(Nc4ccc(N5CCNCC5)cc4)n3)c2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 11.05 | [{"value": 11.05, "product": "COC1=C(C=CC(=C1)N2CCN(CC2)CCO)NC3=NC=C(C(=N3)C4=C5C=CC=CN5N=C4)Cl", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | 3-(2,5-dichloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine (200 mg, 0.75 mmol), 2-(4-(4-amino-3-methoxyphenyl)piperazin-1-yl)ethanol (190 mg, 0.75 mmol), cesium carbonate (295 mg, 0.91 mmol), diacetoxypalladium (13.55 mg, 0.06 mmol) and (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (41.8 mg, 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.c1ccn2nccc2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC | 140 | null | COc1cc(N2CCN(CCO)CC2)ccc1N.Clc1ncc(Cl)c(-c2cnn3ccccc23)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(N2CCN(CCO)CC2)ccc1Nc1ncc(Cl)c(-c2cnn3ccccc23)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-587e8b015ef542aa9ba95a064a0d6902 | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1ccc(Br)cc1>>CC(C)(C)OC(=O)N1CCN(c2ccc(C#N)cc2)CC1 | C1=CC(=CC=C1C#N)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=C(C=C2)C#N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:20][CH2:21]1.Br[c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1 | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1ccc(Br)cc1 | CC(C)(C)OC(=O)N1CCN(c2ccc(C#N)cc2)CC1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 82.34 | [{"value": 82.34, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=C(C=C2)C#N", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | To 4-bromobenzonitrile (.5 g, 2.75 mmol) dissolved in dry THF (10 mL) was added tert-butyl piperazine-1-carboxylate (0.512 g, 2.75 mmol), Sodium-t- butoxide (0.792 g, 8.24 mmol) and purged with N2 gas for 10 min followed by the addition of 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl (0.131 g, 0.27 mmo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].C1CCOC1 | 120 | null | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1ccc(Br)cc1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].C1CCOC1>CC(C)(C)OC(=O)N1CCN(c2ccc(C#N)cc2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-088bd21d086a43258b728521904f368d | CN1CCNCC1.COc1cc(Br)cc([N+](=O)[O-])c1>>COc1cc(N2CCN(C)CC2)cc([N+](=O)[O-])c1 | COC1=CC(=CC(=C1)[N+](=O)[O-])Br.CN1CCNCC1>>CN1CCN(CC1)C2=CC(=CC(=C2)OC)[N+](=O)[O-] | [NH:6]1[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:18][c:14]([N+:15](=[O:16])[O-:17])[cH:13]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)[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | CN1CCNCC1.COc1cc(Br)cc([N+](=O)[O-])c1 | COc1cc(N2CCN(C)CC2)cc([N+](=O)[O-])c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 71.17 | [{"value": 71.17, "product": "CN1CCN(CC1)C2=CC(=CC(=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 1-bromo-3-methoxy-5-nitrobenzene (116 mg, 0.5 mmol), 1-methylpiperazine (167 µl, 1.50 mmol), Palladium(II) acetate (11.23 mg, 0.05 mmol), BINAP (31.1 mg, 0.05 mmol), Cs2CO3 (326 mg, 1.00 mmol) and PhCH3 (10 mL) were added to a 100ml rb flask and heated at 150 °C for 1h. LCMS showed rxn done with desired product formed... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 150 | null | CN1CCNCC1.COc1cc(Br)cc([N+](=O)[O-])c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1cc(N2CCN(C)CC2)cc([N+](=O)[O-])c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-29003fa36fea4ddebef83b29dba29c7c | COc1cc(I)ccc1Br.NC1COC1>>COc1cc(NC2COC2)ccc1Br | COC1=C(C=CC(=C1)I)Br.C1C(CO1)N>>COC1=C(C=CC(=C1)NC2COC2)Br | I[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:13]([Br:14])[cH:12][cH:11]1.[NH2:6][CH:7]1[CH2:8][O:9][CH2:10]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH:7]2[CH2:8][O:9][CH2:10]2)[cH:11][cH:12][c:13]1[Br:14] | COc1cc(I)ccc1Br.NC1COC1 | COc1cc(NC2COC2)ccc1Br | 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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2COC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]1-[C:8]-[#8:9]-[C:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]1-[C:8]-[#8:9]-[C:10]-1):[c:4]:[c:5] | 35.77 | [{"value": 35.77, "product": "COC1=C(C=CC(=C1)NC2COC2)Br", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | A solution of 1-bromo-4-iodo-2-methoxybenzene (0.60 g, 1.92 mmol) dissolved in toluene (15 mL) was treated with oxetan-3-amine (0.140 g, 1.92 mmol), SODIUM TERT-BUTOXIDE (0.221 g, 2.30 mmol), XANTPHOS (0.111 g, 0.19 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.044 g, 0.05 mmol) under nitrogen. The resulting mi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COC1 | HI | 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 | 80 | null | COc1cc(I)ccc1Br.NC1COC1>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>COc1cc(NC2COC2)ccc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3df00475fe9d41898bd3503e3b2ed03d | CCNc1ccccc1.COc1nc(I)ncc1Br>>CCN(c1ccccc1)c1ncc(Br)c(OC)n1 | COC1=NC(=NC=C1Br)I.CCNC1=CC=CC=C1>>CCN(C1=CC=CC=C1)C2=NC=C(C(=N2)OC)Br | [CH3:1][CH2:2][NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.I[c:10]1[n:11][cH:12][c:13]([Br:14])[c:15]([O:16][CH3:17])[n:18]1>>[CH3:1][CH2:2][N:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][cH:12][c:13]([Br:14])[c:15]([O:16][CH3:17])[n:18]1 | CCNc1ccccc1.COc1nc(I)ncc1Br | CCN(c1ccccc1)c1ncc(Br)c(OC)n1 | 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] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ncccn2)cc1 | I-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:6]-[C:7]-[N;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 70.78 | [{"value": 70.78, "product": "CCN(C1=CC=CC=C1)C2=NC=C(C(=N2)OC)Br", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 5-bromo-2-iodo-4-methoxypyrimidine (0.086 g, 0.27 mmol), diacetoxypalladium (2.78 mg, 0.01 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) - XantPhos (7.16 mg, 0.01 mmol) and sodium 2-methylbutan-2-olate (0.055 g, 0.50 mmol) and di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (8.88 mg, 0.02 mmol) were ad... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HI | 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].CC1=CC=CC=C1 | 100 | null | CCNc1ccccc1.COc1nc(I)ncc1Br>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].CC1=CC=CC=C1>CCN(c1ccccc1)c1ncc(Br)c(OC)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8bbed4d3f8cb496989e49be7e55b89ca | CCNc1ccccc1.COc1nc(I)ncc1Br>>CCN(c1ccccc1)c1ncc(Br)c(OC)n1 | COC1=NC(=NC=C1Br)I.CCNC1=CC=CC=C1>>CCN(C1=CC=CC=C1)C2=NC=C(C(=N2)OC)Br | [CH3:1][CH2:2][NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.I[c:10]1[n:11][cH:12][c:13]([Br:14])[c:15]([O:16][CH3:17])[n:18]1>>[CH3:1][CH2:2][N:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][cH:12][c:13]([Br:14])[c:15]([O:16][CH3:17])[n:18]1 | CCNc1ccccc1.COc1nc(I)ncc1Br | CCN(c1ccccc1)c1ncc(Br)c(OC)n1 | CCC(C)(C)[O-].[Na+] | CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ncccn2)cc1 | I-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:6]-[C:7]-[N;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 53.74 | [{"value": 53.74, "product": "CCN(C1=CC=CC=C1)C2=NC=C(C(=N2)OC)Br", "details": "", "is_desired": true}] | 60 | CELSIUS | null | null | 5-bromo-2-iodo-4-methoxypyrimidine (0.086 g, 0.27 mmol), diacetoxypalladium (2.78 mg, 0.01 mmol), di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (8.88 mg, 0.02 mmol) and sodium 2-methylbutan-2-olate (0.033 g, 0.30 mmol) were added to a micro vial. Then N-ethylaniline (0.031 mL, 0.25 mmol) in toluene (1.5 mL) was added t... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HI | CCC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 60 | null | CCNc1ccccc1.COc1nc(I)ncc1Br>CCC(C)(C)[O-].[Na+].CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CCN(c1ccccc1)c1ncc(Br)c(OC)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-839e83634a9943b98e2511e3c8112ffb | C1CNCCN1.CC(C)(C)OC(=O)Nc1cc(Br)ccc1Cl>>CC(C)(C)OC(=O)Nc1cc(N2CCNCC2)ccc1Cl | CC(C)(C)OC(=O)NC1=C(C=CC(=C1)Br)Cl.C1CNCCN1>>CC(C)(C)OC(=O)NC1=C(C=CC(=C1)N2CCNCC2)Cl | [NH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1.Br[c:11]1[cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:20]([Cl:21])[cH:19][cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[cH:18][cH:19][c:20]1[Cl:21] | C1CNCCN1.CC(C)(C)OC(=O)Nc1cc(Br)ccc1Cl | CC(C)(C)OC(=O)Nc1cc(N2CCNCC2)ccc1Cl | 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 | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:2]:[c:3] | 57.11 | [{"value": 57.11, "product": "CC(C)(C)OC(=O)NC1=C(C=CC(=C1)N2CCNCC2)Cl", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | palladium(II) acetate (0.110 g, 0.49 mmol), BINAP (0.244 g, 0.39 mmol) and CS2CO3 (1.594 g, 4.89 mmol) were added to a mixture of [Reactants] and piperazine (2.76 g, 32.10 mmol) in toluene (10 mL), The suspension were heated to 110 °C for 16 hours, LCMS showed product mass [M+1]:312.0 at retention time RT=1.69 min (pol... | 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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | C1CNCCN1.CC(C)(C)OC(=O)Nc1cc(Br)ccc1Cl>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)Nc1cc(N2CCNCC2)ccc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9a38e3cdbd7649cb80e5076ddc46669b | Cc1ncc([N+](=O)[O-])cc1Br.Nc1nccc(-c2cccnc2)n1>>Cc1ncc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | CC1=C(C=C(C=N1)[N+](=O)[O-])Br.C1=CC(=CN=C1)C2=NC(=NC=C2)N>>CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3 | Br[c:10]1[c:2]([CH3:1])[n:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9]1.[NH2:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1>>[CH3:1][c:2]1[n:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1 | Cc1ncc([N+](=O)[O-])cc1Br.Nc1nccc(-c2cccnc2)n1 | Cc1ncc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2nccc(-c3cccnc3)n2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13]>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13] | 18.86 | [{"value": 18.86, "product": "CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Palladium(II) acetate (65.3 mg, 0.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (336 mg, 0.58 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Toluene (35 ml) was added and the resulting mixture was heated to to 50°C for 45 minutes. To this mixture was added... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cncnc1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 90 | null | Cc1ncc([N+](=O)[O-])cc1Br.Nc1nccc(-c2cccnc2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Cc1ncc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-93068c36902748b0a097205076445ea2 | Cc1ncc([N+](=O)[O-])cc1Br.Nc1nccc(-c2cccnc2)n1>>Cc1ncc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | CC1=C(C=C(C=N1)[N+](=O)[O-])Br.C1=CC(=CN=C1)C2=NC(=NC=C2)N>>CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3 | Br[c:10]1[c:2]([CH3:1])[n:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9]1.[NH2:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1>>[CH3:1][c:2]1[n:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[n:23]1 | Cc1ncc([N+](=O)[O-])cc1Br.Nc1nccc(-c2cccnc2)n1 | Cc1ncc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2nccc(-c3cccnc3)n2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13]>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13] | 21.22 | [{"value": 21.22, "product": "CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Palladium(II) acetate (65.3 mg, 0.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (336 mg, 0.58 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Toluene (35 ml) was added and the resulting mixture was heated to to 50°C for 45 minutes, then cooled to r.t. To th... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cncnc1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 90 | null | Cc1ncc([N+](=O)[O-])cc1Br.Nc1nccc(-c2cccnc2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Cc1ncc([N+](=O)[O-])cc1Nc1nccc(-c2cccnc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a304a5abe5a040c6b1e32d87d537c8dc | Clc1cccc(Cl)n1.Nc1ccccc1>>Clc1cccc(Nc2ccccc2)n1 | C1=CC(=NC(=C1)Cl)Cl.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=NC(=CC=C2)Cl | Cl[c:6]1[cH:5][cH:4][cH:3][c:2]([Cl:1])[n:14]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14]1 | Clc1cccc(Cl)n1.Nc1ccccc1 | Clc1cccc(Nc2ccccc2)n1 | 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 | 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] | 52.97 | [{"value": 52.97, "product": "C1=CC=C(C=C1)NC2=NC(=CC=C2)Cl", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | 2,6-dichloropyridine (228 mg, 1.54 mmol) was dissolved in toluene (7.5 ml) and diacetoxypalladium (6 mg, 0.03 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (19 mg, 0.03 mmol), aniline (0.170 ml, 1.87 mmol) and potassium carbonate (583 mg, 4.22 mmol) were added added. The reaction mixture was sparged with notrog... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | 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 | 160 | null | Clc1cccc(Cl)n1.Nc1ccccc1>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>Clc1cccc(Nc2ccccc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-838ef353b3e04bbf8250b3f17d8c966f | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1>>C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl | C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N.C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl>>C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F | [CH3:1][C@H:2]1[CH2:3][C@H:4]([NH2:5])[CH2:19][CH2:20][N:21]1[C:22](=[O:23])[c:24]1[cH:25][n:26][n:27]([CH3:28])[c:29]1[Cl:30].Cl[c:6]1[cH:7][c:8](=[O:9])[nH:10][c:11]2[cH:12][c:13]([F:14])[c:15]([F:16])[cH:17][c:18]12>>[CH3:1][C@H:2]1[CH2:3][C@H:4]([NH:5][c:6]2[cH:7][c:8](=[O:9])[nH:10][c:11]3[cH:12][c:13]([F:14])[c:1... | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1 | C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1cn[nH]c1)N1CCC(Nc2cc(=O)[nH]c3ccccc23)CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:13] | 8.48 | [{"value": 8.48, "product": "C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | In a 25ml Biotage microwave vial, 4-chloro-6,7-difluoroquinolin-2(1H)-one (0.175 g, 0.81 mmol), ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone (0.208 g, 0.81 mmol) ,racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.051 g, 0.08 mmol), Cesium carbonate (0.793 g, 2.44 mmol), Pall... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 140 | null | C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a5d4f788c47d4d46a04a4c8af6024836 | CC1(CN)COC1.Clc1cccnc1Br>>CC1(CNc2ncccc2Cl)COC1 | C1=CC(=C(N=C1)Br)Cl.CC1(COC1)CN>>CC1(COC1)CNC2=C(C=CC=N2)Cl | [CH3:1][C:2]1([CH2:3][NH2:4])[CH2:12][O:13][CH2:14]1.Br[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[Cl:11]>>[CH3:1][C:2]1([CH2:3][NH:4][c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[Cl:11])[CH2:12][O:13][CH2:14]1 | CC1(CN)COC1.Clc1cccnc1Br | CC1(CNc2ncccc2Cl)COC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2COC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | 12.22 | [{"value": 12.22, "product": "CC1(COC1)CNC2=C(C=CC=N2)Cl", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | In a 5 MW vial, Pd2((dba)3 (7.23 mg, 7.90 µmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (9.71 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (174 mg, 1.81 mmol), (3-methyloxetan-3-yl)methanamine (126 mg, 1.25 mmol) and 2-bromo-3-chloropyridine (200 mg, 1.04 mmol) mixed in toluene (2 mL) to give a brown ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1COC1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 115 | null | CC1(CN)COC1.Clc1cccnc1Br>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>CC1(CNc2ncccc2Cl)COC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-218b24f2d22444388b751f136d342319 | Brc1cccnc1.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2c1cccnc1 | C1=CC(=CN=C1)Br.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CN=CC=C3 | Br[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][NH:14]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][N:14]2[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1 | Brc1cccnc1.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2c1cccnc1 | 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 | 283b1960c227387bf15bed917434ac19c87410d6f8e202e473586b792b097580 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2C[C@@H]3C[C@H]2CN3)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]2-[C:10]-[C:11]-1-[C:12]-[NH;D2;+0:13]-2>>[#7:7]1-[C:8]-[C:9]2-[C:10]-[C:11]-1-[C:12]-[N;H0;D3;+0:13]-2-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 98.65 | [{"value": 98.65, "product": "CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CN=CC=C3", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.055 g, 0.06 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.075 g, 0.12 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (29.7 ml) was added and the resulting mixture heated to 90°C for 10 minutes then cooled to room temperature. ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1[NH][C@@H]2CN[C@H]1C2 | C1[NH][C@@H]2C[NH][C@H]1C2.c1ccncc1 | C1[NH][C@@H]2C[NH][C@H]1C2.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 | 85 | null | Brc1cccnc1.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>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>CC(C)(C)OC(=O)N1C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4e29f7f8d4e94f93bbf63ba519f77a6e | C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1cccc(Br)c1)C12CCC(CC1)N2C>>Cc1cccc(C)c1C(=O)NC(c1cccc(N2CCOCC2)c1)C12CCC(CC1)N2C | CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC(=CC=C2)Br)C34CCC(N3C)CC4.C1COCCN1>>CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC(=CC=C2)N3CCOCC3)C45CCC(N4C)CC5 | [NH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1.Br[c:17]1[cH:16][cH:15][cH:14][c:13]([CH:12]([NH:11][C:9]([c:8]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[CH3:7])=[O:10])[C:25]23[CH2:26][CH2:27][CH:28]([CH2:29][CH2:30]2)[N:31]3[CH3:32])[cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[C:9](=[O:10])[NH:11][CH:12... | C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1cccc(Br)c1)C12CCC(CC1)N2C | Cc1cccc(C)c1C(=O)NC(c1cccc(N2CCOCC2)c1)C12CCC(CC1)N2C | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(NC(c1cccc(N2CCOCC2)c1)C12CCC(CC1)N2)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:2]:[c:3] | 17.99 | [{"value": 17.99, "product": "CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC(=CC=C2)N3CCOCC3)C45CCC(N4C)CC5", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | To a suspension of N-((3-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (0.040 g, 0.09 mmol), MORPHOLINE (8.97 µL, 0.10 mmol), BINAP (5.83 mg, 9.36 µmol), and sodium tert-butoxide (0.013 g, 0.14 mmol) in toluene (2 mL) was added palladium(II) acetate (1.051 mg, 4.68 µmol). Nitrogen w... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | C1CC2CCC1[NH]2.c1ccccc1.c1ccccc1.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.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1cccc(Br)c1)C12CCC(CC1)N2C>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Cc1cccc(C)c1C(=O)NC(c1cccc(N2CCOCC2)c1)C12CCC(CC1)N2C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-59c6d21cb6354f44a2ed185cff3caeb9 | COc1ccc(CN)cc1.Clc1ccnc(Nc2ccccc2)c1>>COc1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.COC1=CC=C(C=C1)CN>>COC1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:22][cH:23]1.Cl[c:9]1[cH:10][cH:11][n:12][c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21]2)[cH:22][cH:23]1 | COc1ccc(CN)cc1.Clc1ccnc(Nc2ccccc2)c1 | COc1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 67.69 | [{"value": 67.69, "product": "COC1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (4-methoxyphenyl)methanamine (73.7 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | COc1ccc(CN)cc1.Clc1ccnc(Nc2ccccc2)c1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>COc1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-be64b42a88614cc79bed55017a7f5289 | Brc1ccc(I)cc1.c1ccc2c(c1)CNC2>>Brc1ccc(N2Cc3ccccc3C2)cc1 | C1=CC(=CC=C1Br)I.C1C2=CC=CC=C2CN1>>C1C2=CC=CC=C2CN1C3=CC=C(C=C3)Br | I[c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:16][cH:15]1.[NH:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[CH2:14]2)[cH:15][cH:16]1 | Brc1ccc(I)cc1.c1ccc2c(c1)CNC2 | Brc1ccc(N2Cc3ccccc3C2)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 | 456c4eabd59dbf908b00b5186945ecf6882e3364bd756c218ec4b6c3f131e7d0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2Cc3ccccc3C2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]1-[NH;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:7]1-[C:6]-[c:10]:[c:9]-[C:8]-1):[c:4]:[c:5] | 48.3 | [{"value": 48.3, "product": "C1C2=CC=CC=C2CN1C3=CC=C(C=C3)Br", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | palladium(II) acetate (0.112 g, 0.50 mmol) and XANTPHOS (0.288 g, 0.50 mmol) were added to a degassed solution of isoindoline (0.566 ml, 4.98 mmol), 1-bromo-4-iodobenzene (1.41 g, 4.98 mmol) and SODIUM TERT-BUTOXIDE (1.197 g, 12.46 mmol) in toluene (49.3 ml) under nitrogen. The resulting solution was stirred at 100 °C ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CNC2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HI | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | Brc1ccc(I)cc1.c1ccc2c(c1)CNC2>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>Brc1ccc(N2Cc3ccccc3C2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9a8d9c41c7b94faa97814a83a1ab2d95 | CN1CC(N)C1.Clc1cccnc1Br>>CN1CC(Nc2ncccc2Cl)C1 | C1=CC(=C(N=C1)Br)Cl.CN1CC(C1)N.Cl>>CN1CC(C1)NC2=C(C=CC=N2)Cl | [CH3:1][N:2]1[CH2:3][CH:4]([NH2:5])[CH2:13]1.Br[c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[CH3:1][N:2]1[CH2:3][CH:4]([NH:5][c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[Cl:12])[CH2:13]1 | CN1CC(N)C1.Clc1cccnc1Br | CN1CC(Nc2ncccc2Cl)C1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CNC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]1-[C:9]-[#7:10]-[C:11]-1):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "CN1CC(C1)NC2=C(C=CC=N2)Cl", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | Pd2(dba)3 (0.018 g, 0.02 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.024 g, 0.04 mmol) and toluene (4 mL) was added to a flask. 2-bromo-3-chloropyridine (0.5 g, 2.60 mmol), 1-methylazetidin-3-amine hydrochloride (0.414 g, 3.38 mmol) and sodium 2-methylpropan-2-olate (0.624 g, 6.50 mmol) was added,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | C1C[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 | 115 | null | CN1CC(N)C1.Clc1cccnc1Br>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>CN1CC(Nc2ncccc2Cl)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d16088bf6acb4600ad776547cf486a02 | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1cc(F)cc(Br)c1>>CC(C)(C)OC(=O)N1CCN(c2cc(F)cc(C(=O)O)c2)CC1 | COC(=O)C1=CC(=CC(=C1)Br)F.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=CC(=C2)C(=O)O)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:22][CH2:23]1.C[O:20][C:18]([c:17]1[cH:16][c:14]([F:15])[cH:13][c:12](Br)[cH:21]1)=[O:19]>>[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][c:14]([F:15])[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21]2... | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1cc(F)cc(Br)c1 | CC(C)(C)OC(=O)N1CCN(c2cc(F)cc(C(=O)O)c2)CC1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 008e31926b32709253c4e936bc924757f3e17810860f733b12d326719f464cba | 154ad2504fb7aaca0f52c4b8eebdfca329f4106b95adc3c71ff059886f074b58 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[#7:9]-[C:10]-[C:11]-1):[c:2]:[c:3] | 71.85 | [{"value": 71.85, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=CC(=C2)C(=O)O)F", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | To methyl 3-bromo-5-fluorobenzoate (1.5 g, 6.44 mmol) dissolved in dry THF (20 mL) was added tert-butyl piperazine-1-carboxylate (1.199 g, 6.44 mmol), Sodium-t-butoxide (1.856 g, 19.31 mmol) and purged with N2 gas for 10 min followed by the addition of2-(Dicyclohexylphosphino)-2',4',6'-tri-i- propyl-1,1'-biphenyl (0.30... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Ester.Secondary amine | Carboxylic acid.Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].C1CCOC1 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1cc(F)cc(Br)c1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].C1CCOC1>CC(C)(C)OC(=O)N1CCN(c2cc(F)cc(C(=O)O)c2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b3e000ca67494471adc7944fbfb45b78 | CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1>>CC1(C)Cc2c(-c3cc(NC(=O)[C@@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)cnn2C1 | CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)Cl)C.CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C1)C(=O)N>>CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C | [NH2:10][C:11](=[O:12])[C@@H:13]1[CH2:14][CH2:15][CH2:16][C@@H:17]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]1.Cl[c:9]1[cH:8][c:7](-[c:6]2[c:5]3[n:33]([n:32][cH:31]2)[CH2:34][C:2]([CH3:1])([CH3:3])[CH2:4]3)[c:29]([F:30])[cH:28][n:27]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[c:6](-[c:7]3[cH:8][... | CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1 | CC1(C)Cc2c(-c3cc(NC(=O)[C@@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)cnn2C1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 89406f6003d7588878359acf2bb1006fd786f9174801801902e1a3d2e230168f | 47ae35855ccafd300e43853a48eb35943d6c3debbccbbdff01a4334f15733fcc | O=C(Nc1cc(-c2cnn3c2CCC3)ccn1)C1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 84.39 | [{"value": 84.39, "product": "CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Tetrakis(triphenylphosphine)palladium(0) (0.094 g, 0.08 mmol) was added to Racemic tert-butyl ((1R,3R)-3-carbamoylcyclohexyl)carbamate (0.235 g, 0.97 mmol),3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (0.215 g, 0.81 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amide | Secondary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1.c1cc2n(n1)CCC2 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].C1COCCO1 | 100 | null | CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C(N)=O)C1.CC1(C)Cc2c(-c3cc(Cl)ncc3F)cnn2C1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3dc45e0d006e4925b34d5e9919e16fc1 | CC(C)(C)OC(=O)N1CCNCC1.CCOc1ccc(Br)cc1Cl>>CCOc1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1Cl | CCOC1=C(C=C(C=C1)Br)Cl.CC(C)(C)OC(=O)N1CCNCC1>>CCOC1=C(C=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C)Cl | [NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.Br[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:22]([Cl:23])[cH:21]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[... | CC(C)(C)OC(=O)N1CCNCC1.CCOc1ccc(Br)cc1Cl | CCOc1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CCOC1=C(C=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | In a 50 mL round-bottomed flask, PALLADIUM ACETATE (0.014 g, 0.06 mmol) was treated with BINAP (0.079 g, 0.13 mmol) under nitrogen in degassed Toluene (12.74 ml). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxylate (0.237 g, 1.27 mmol), cesium car... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.CCOc1ccc(Br)cc1Cl>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CCOc1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a7c71c7b356644fcbb6f6b90814539ca | CN(C)CCN.COc1cc(I)ccc1Br>>COc1cc(NCCN(C)C)ccc1Br | COC1=C(C=CC(=C1)I)Br.CN(C)CCN>>CN(C)CCNC1=CC(=C(C=C1)Br)OC | [NH2:6][CH2:7][CH2:8][N:9]([CH3:10])[CH3:11].I[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:14]([Br:15])[cH:13][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH2:7][CH2:8][N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[Br:15] | CN(C)CCN.COc1cc(I)ccc1Br | COc1cc(NCCN(C)C)ccc1Br | 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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 45.64 | [{"value": 45.64, "product": "CN(C)CCNC1=CC(=C(C=C1)Br)OC", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | A solution of 1-bromo-4-iodo-2-methoxybenzene (0.63 g, 2.01 mmol) dissolved in toluene (15.73 ml) was treated with N1,N1-dimethylethane-1,2-diamine (0.177 g, 2.01 mmol), SODIUM TERT-BUTOXIDE (0.232 g, 2.42 mmol), XANTPHOS (0.116 g, 0.20 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) under nitro... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | 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 | 80 | null | CN(C)CCN.COc1cc(I)ccc1Br>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>COc1cc(NCCN(C)C)ccc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-effcbe0533904d0880f0ace9776ccb21 | CNC(=O)c1cc(Cl)nc(Cl)c1.Nc1ccccc1>>CNC(=O)c1cc(Cl)nc(Nc2ccccc2)c1 | CNC(=O)C1=CC(=NC(=C1)Cl)Cl.C1=CC=C(C=C1)N>>CNC(=O)C1=CC(=NC(=C1)Cl)NC2=CC=CC=C2 | Cl[c:10]1[n:9][c:7]([Cl:8])[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | CNC(=O)c1cc(Cl)nc(Cl)c1.Nc1ccccc1 | CNC(=O)c1cc(Cl)nc(Nc2ccccc2)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] | CC1=CC=CC=C1 | 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]-[C:6](-[#7:7])=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#7:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:[c:3] | 52.86 | [{"value": 52.86, "product": "CNC(=O)C1=CC(=NC(=C1)Cl)NC2=CC=CC=C2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | SODIUM TERT-BUTOXIDE (0.984 g, 10.24 mmol) was added to 2,6-dichloro-N- methylisonicotinamide (1.5 g, 7.32 mmol), ANILINE (0.667 mL, 7.32 mmol), PALLADIUM(II) ACETATE (0.016 g, 0.07 mmol) and XANTPHOS (0.127 g, 0.22 mmol) in toluene (30 mL) under nitrogen. The resulting mixture was stirred at 80 °C for 4 hours. The rea... | 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].CC1=CC=CC=C1 | 80 | null | CNC(=O)c1cc(Cl)nc(Cl)c1.Nc1ccccc1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CNC(=O)c1cc(Cl)nc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2ad8db0a7ea741b0a4428eec268f91fd | Clc1ccnc(Nc2ccccc2)c1.NCc1cccc(F)c1>>Fc1cccc(CNc2ccnc(Nc3ccccc3)c2)c1 | C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl.C1=CC(=CC(=C1)F)CN>>C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC(=CC=C3)F | Cl[c:9]1[cH:10][cH:11][n:12][c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:22]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21]2)[cH:22]1 | Clc1ccnc(Nc2ccccc2)c1.NCc1cccc(F)c1 | Fc1cccc(CNc2ccnc(Nc3ccccc3)c2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:7]:1 | 58.6 | [{"value": 58.6, "product": "C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC(=CC=C3)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (3-fluorophenyl)methanamine (67.3 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSP... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 100 | null | Clc1ccnc(Nc2ccccc2)c1.NCc1cccc(F)c1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Fc1cccc(CNc2ccnc(Nc3ccccc3)c2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1342ffbeb4634245a6963094cc9535b6 | Brc1ccc(I)cc1.C1CCN(C2CCNCC2)CC1>>Brc1ccc(N2CCC(N3CCCCC3)CC2)cc1 | C1=CC(=CC=C1Br)I.C1CCN(CC1)C2CCNCC2>>C1CCN(CC1)C2CCN(CC2)C3=CC=C(C=C3)Br | I[c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:19][cH:18]1.[NH:6]1[CH2:7][CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:16][CH2:17]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH:9]([N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[CH2:16][CH2:17]2)[cH:18][cH:19]1 | Brc1ccc(I)cc1.C1CCN(C2CCNCC2)CC1 | Brc1ccc(N2CCC(N3CCCCC3)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.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCC(N3CCCCC3)CC2)cc1 | I-[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] | 64.41 | [{"value": 64.41, "product": "C1CCN(CC1)C2CCN(CC2)C3=CC=C(C=C3)Br", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.162 g, 0.18 mmol) was added to 1,4'-bipiperidine (0.595 g, 3.53 mmol), 1-bromo-4-iodobenzene (1.000 g, 3.53 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.205 g, 0.35 mmol) and sodium 2-methylpropan-2-olate (0.408 g, 4.24 mmol) in toluene (10 mL). The res... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.C1CC[NH]CC1 | HI | 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 | 80 | null | Brc1ccc(I)cc1.C1CCN(C2CCNCC2)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>Brc1ccc(N2CCC(N3CCCCC3)CC2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f42610ca5d2c4f39b60de444b5b2b82f | CCOc1ccc(Br)cc1OC.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>>CCOc1ccc(N2CCN[C@H](C)C2)cc1OC | CCOC1=C(C=C(C=C1)Br)OC.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>>CCOC1=C(C=C(C=C1)N2CCN[C@@H](C2)C)OC | Br[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:16]([O:17][CH3:18])[cH:15]1.CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][NH:8][CH2:14][C@H:12]1[CH3:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][C@H:12]([CH3:13])[CH2:14]2)[cH:15][c:16]1[O:17][CH3:18] | CCOc1ccc(Br)cc1OC.C[C@@H]1CNCCN1C(=O)OC(C)(C)C | CCOc1ccc(N2CCN[C@H](C)C2)cc1OC | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 1155a782af40ddd9c7c7ab45b40bc8450f26a553a41c0f0d5dfec075d80a69f3 | 4692e9cfac8ca0f49eb5c33838ae1fa5c1a375a44556f0da8885d569da661aa1 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1-[C;D1;H3:12]>>[C;D1;H3:12]-[C:11]1-[C:10]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:8]-[C:7]-[NH;D2;+0:6]-1 | 50.77 | [{"value": 50.77, "product": "CCOC1=C(C=C(C=C1)N2CCN[C@@H](C2)C)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (0.049 g, 0.22 mmol)and (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.108 g, 0.17 mmol) were added to 4-bromo-1-ethoxy-2-methoxybenzene (1 g, 4.33 mmol),(R)-1-N-Boc-2-methyl piperazine (0.867 g, 4.33 mmol) and Sodium tert- butoxide (0.624 g, 6.49 mmol) in anhydrous Toluene (20 mL) under a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CCOc1ccc(Br)cc1OC.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CCOc1ccc(N2CCN[C@H](C)C2)cc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3ee1bec4d5b244e8a0d82f023c1c6526 | CC(C)(C)OC(=O)N1CCNCC1.CN(C)c1ccccc1Br>>CN(C)c1ccccc1N1CCN(C(=O)OC(C)(C)C)CC1 | CN(C)C1=CC=CC=C1Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2N(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:4]([N:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][cH:8]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][... | CC(C)(C)OC(=O)N1CCNCC1.CN(C)c1ccccc1Br | CN(C)c1ccccc1N1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 31.99 | [{"value": 31.99, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2N(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium (II) acetate (67.3 mg, 0.30 mmol) and 2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (280 mg, 0.60 mmol) were dissolved in toluene (7 mL) and purged with nitrogen. The mixture was warmed to 50°C for 15 mins. In a separate vessel, were mixed 2-bromo-N,N-dimethylaniline (600 mg, 3.00 mmol), tert-buty... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(=O)N1CCNCC1.CN(C)c1ccccc1Br>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CN(C)c1ccccc1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7d6438f5772442a8addd4f9357140a8b | CC(C)(C)OC(=O)N1CCNCC1.COc1ccccc1Cl>>COc1ccccc1N1CCN(C(=O)OC(C)(C)C)CC1 | COC1=CC=CC=C1Cl.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC | [NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.Cl[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccccc1Cl | COc1ccccc1N1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 11.22 | [{"value": 11.22, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | RuPhos (32.7 mg, 0.07 mmol) and palladium (II) acetate (15.75 mg, 0.07 mmol) were suspended in toluene (1 mL) at ambient temperature. The mixture was degassed and purged with nitrogen several times and warmed to 50°C for 20 mins. In a separate vessel were mixed 1-chloro-2-methoxybenzene (100 mg, 0.70 mmol), tert-butyl... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HCl | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccccc1Cl>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1ccccc1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6baac44dbbb745bfaa3ee3e69cefbcee | C[C@H]1CNCCN1C.Cc1cc(Cl)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1>>Cc1cc(N2CCN(C)[C@@H](C)C2)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 | CC1=CC(=NC=C1C2=CC=C(C=C2)C3=NC4=C(C=CC=C4C(=O)N3)CO)Cl.C[C@H]1CNCCN1C>>C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO | [NH:5]1[CH2:6][CH2:7][N:8]([CH3:9])[C@@H:10]([CH3:11])[CH2:12]1.Cl[c:4]1[cH:3][c:2]([CH3:1])[c:15](-[c:16]2[cH:17][cH:18][c:19](-[c:20]3[n:21][c:22]4[c:23]([CH2:24][OH:25])[cH:26][cH:27][cH:28][c:29]4[c:30](=[O:31])[nH:32]3)[cH:33][cH:34]2)[cH:14][n:13]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[C@@H... | C[C@H]1CNCCN1C.Cc1cc(Cl)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 | Cc1cc(N2CCN(C)[C@@H](C)C2)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(-c2ccc(-c3ccc(N4CCNCC4)nc3)cc2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a: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] | 26.54 | [{"value": 26.54, "product": "C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A mixture of CHLORO(2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I- PROPOXY-1,1'-BIPHENYL)[2-(2-AMINOETHYLPHENYL)]PALLADIUM(II), METHYL-T- BUTYLETHER ADDUCT (Ru Phos Pd cycle) (43.2 mgs, 0.1eq), sodium tert-butoxide (229 mg, 2.38 mmol), 2-(4-(6-chloro-4-methylpyridin-3-yl)phenyl)-8-(hydroxymethyl)quinazolin-4(3H)-one (250 mg, 0.53... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccncc1 | c1ccncc1.C1C[NH]CC[NH]1 | c1ccncc1.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2ccccc2n1 | HCl | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+].C1COCCO1 | 110 | null | C[C@H]1CNCCN1C.Cc1cc(Cl)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+].C1COCCO1>Cc1cc(N2CCN(C)[C@@H](C)C2)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-135c33d2da2b4d7f90276e4b49e654c9 | C[C@H]1CNCCN1C.Cc1cc(Cl)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1>>Cc1cc(N2CCN(C)[C@@H](C)C2)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 | CC1=CC(=NC=C1C2=CC=C(C=C2)C3=NC4=C(C=CC=C4C(=O)N3)CO)Cl.C[C@H]1CNCCN1C>>C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO | [NH:5]1[CH2:6][CH2:7][N:8]([CH3:9])[C@@H:10]([CH3:11])[CH2:12]1.Cl[c:4]1[cH:3][c:2]([CH3:1])[c:15](-[c:16]2[cH:17][cH:18][c:19](-[c:20]3[n:21][c:22]4[c:23]([CH2:24][OH:25])[cH:26][cH:27][cH:28][c:29]4[c:30](=[O:31])[nH:32]3)[cH:33][cH:34]2)[cH:14][n:13]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[C@@H... | C[C@H]1CNCCN1C.Cc1cc(Cl)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 | Cc1cc(N2CCN(C)[C@@H](C)C2)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(-c2ccc(-c3ccc(N4CCNCC4)nc3)cc2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a: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] | 34.73 | [{"value": 34.73, "product": "C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | A mixture of CHLORO(2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I- PROPOXY-1,1'-BIPHENYL)[2-(2-AMINOETHYLPHENYL)]PALLADIUM(II), METHYL-T- BUTYLETHER ADDUCT (Ru Phos Pd cycle) (69.2 mgs, 0.2eq), sodium tert-butoxide (244 mg, 2.54 mmol) ,2-(4-(6-chloro-4-methylpyridin-3-yl)phenyl)-8-(hydroxymethyl)quinazolin-4(3H)-one (200 mg, 0.42... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccncc1 | c1ccncc1.C1C[NH]CC[NH]1 | c1ccncc1.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2ccccc2n1 | HCl | CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+].C1COCCO1 | 115 | null | C[C@H]1CNCCN1C.Cc1cc(Cl)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1>CC(C)(C)[O-].[Na+].CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+].C1COCCO1>Cc1cc(N2CCN(C)[C@@H](C)C2)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e0d3875cf2584a84afda6341abdff6dc | Brc1ccc(I)cn1.C1COCCN1>>Brc1ccc(N2CCOCC2)cn1 | C1=CC(=NC=C1I)Br.C1COCCN1>>C1COCCN1C2=CN=C(C=C2)Br | I[c:5]1[cH:4][cH:3][c:2]([Br:1])[n:13][cH:12]1.[NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][n:13]1 | Brc1ccc(I)cn1.C1COCCN1 | Brc1ccc(N2CCOCC2)cn1 | 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 | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:3]1:[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]:[c:5]:[c:4]:1 | 56.05 | [{"value": 56.05, "product": "C1COCCN1C2=CN=C(C=C2)Br", "details": "", "is_desired": true}] | 20 | CELSIUS | null | null | Pd2(dba)3 (0.564 g, 0.62 mmol) was added to 2-bromo-5-iodopyridine (5.00 g, 17.61 mmol), morpholine (1.541 mL, 17.61 mmol), sodium tert-butoxide (4.23 g, 44.03 mmol) and Xantphos (1.019 g, 1.76 mmol) in toluene (200 mL) at 20°C. The resulting solution was stirred at r.t. for 3 days (as the reaction was started on a Fri... | 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 | HI | 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 | 20 | null | Brc1ccc(I)cn1.C1COCCN1>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>Brc1ccc(N2CCOCC2)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-be476d7266d0479ba1e6c4f9e5b26400 | CC(C)(C)OC(=O)NCC(=O)N1CCn2c(nc(-c3ccc(F)cc3)c2Br)C1(C)C.Nc1ccc(F)cc1>>CC(C)(C)OC(=O)NCC(=O)N1CCn2c(nc(-c3ccc(F)cc3)c2Nc2ccc(F)cc2)C1(C)C | CC1(C2=NC(=C(N2CCN1C(=O)CNC(=O)OC(C)(C)C)Br)C3=CC=C(C=C3)F)C.C1=CC(=CC=C1N)F>>CC1(C2=NC(=C(N2CCN1C(=O)CNC(=O)OC(C)(C)C)NC3=CC=C(C=C3)F)C4=CC=C(C=C4)F)C | Br[c:26]1[n:15]2[c:16]([n:17][c:18]1-[c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]1)[C:35]([CH3:36])([CH3:37])[N:12]([C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11])[CH2:13][CH2:14]2.[NH2:27][c:28]1[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O... | CC(C)(C)OC(=O)NCC(=O)N1CCn2c(nc(-c3ccc(F)cc3)c2Br)C1(C)C.Nc1ccc(F)cc1 | CC(C)(C)OC(=O)NCC(=O)N1CCn2c(nc(-c3ccc(F)cc3)c2Nc2ccc(F)cc2)C1(C)C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 0852eaeb8bbf65c56af61d3fe7c5adc007bcbfd9be1c4485ab853e31a5bfcb61 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2c(-c3ccccc3)nc3n2CCNC3)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2](:[c:3]:[#7;a:4]:[c:5]:1-[c:6])-[C:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:7]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5](-[c:6]):[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 83.27 | [{"value": 83.27, "product": "CC1(C2=NC(=C(N2CCN1C(=O)CNC(=O)OC(C)(C)C)NC3=CC=C(C=C3)F)C4=CC=C(C=C4)F)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | In a microwave vial, cesium carbonate (135 mg, 0.42 mmol), 4-fluoroaniline (92 mg, 0.83 mmol), tris(dibenzylideneacetone)dipalladium(0) (19.02 mg, 0.02 mmol), Xantphos (24.04 mg, 0.04 mmol) and dry 1,4-dioxane (6 mL) were stirred for 5 minutes at room temperature. tert-butyl (2-(3-bromo-2-(4-fluorophenyl)-8,8-dimethyl-... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cn2c(n1)C[NH]CC2 | c1cn2c(n1)C[NH]CC2 | c1cn2c(n1)C[NH]CC2.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.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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 | 120 | null | CC(C)(C)OC(=O)NCC(=O)N1CCn2c(nc(-c3ccc(F)cc3)c2Br)C1(C)C.Nc1ccc(F)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-09a52aa0a68e4624905d84eed602571e | COc1cccc(N)c1.FC(F)(F)c1cccc(Br)c1>>COc1cccc(Nc2cccc(C(F)(F)F)c2)c1 | C1=CC(=CC(=C1)Br)C(F)(F)F.COC1=CC=CC(=C1)N>>COC1=CC=CC(=C1)NC2=CC=CC(=C2)C(F)(F)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:19]1.Br[c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]2)[cH:19]1 | COc1cccc(N)c1.FC(F)(F)c1cccc(Br)c1 | COc1cccc(Nc2cccc(C(F)(F)F)c2)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] | COC1=CC=CC=C1 | 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] | 0 | [{"value": 0.0, "product": "COC1=CC=CC(=C1)NC2=CC=CC(=C2)C(F)(F)F", "details": "", "is_desired": true}] | 50 | CELSIUS | null | null | PdOAc2 (8 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (40 mg, 0.07 mmol) were added to a dried vial. The vial was caped with a septa-cap and inerted with nitrogen. Degassed anisole (2 mL)was added and the catalyst mixture was heated to 50ºC for 30 minutes, then cooled down to rt. A dry... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].COC1=CC=CC=C1 | 50 | null | COc1cccc(N)c1.FC(F)(F)c1cccc(Br)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].COC1=CC=CC=C1>COc1cccc(Nc2cccc(C(F)(F)F)c2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4b267760e4484094b4eaffe00a0fdfde | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cccc(Br)c1>>CC(C)(C)OC(=O)N1CC2CC1CN2c1cccc(C(F)(F)F)c1 | C1=CC(=CC(=C1)Br)C(F)(F)F.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][NH:14]2.Br[c:15]1[cH:16][cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]2[CH2:11][CH:12]1[CH2:13][N:14]2[c:15]1[cH:16][cH:17][cH:18][c:19]([C:2... | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cccc(Br)c1 | CC(C)(C)OC(=O)N1CC2CC1CN2c1cccc(C(F)(F)F)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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 19017c1238f901bf9ddad6509879cf8dac1766119d94f3214f1bbbb3554bb0d6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CC3CC2CN3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]1-[C:14]-[C@@H;D3;+0:15]2-[C:16]-[C:17]-1-[C:18]-[NH;D2;+0:19]-2>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]1-[C:14]-[CH;D3;+0:15]2-[C:16]-[C:17]-1-[C:1... | 99.36 | [{"value": 99.36, "product": "CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | A 50 ml round bottom equipped with stir bar was charged with binap (0.219 g, 0.34 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.132 g, 0.14 mmol) dissolved in dioxane (6 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 1-bromo-3-(trifluoromethyl)benzene (0.301 mL, 2.16 mmol) follow... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1[NH][C@@H]2CN[C@H]1C2.c1ccccc1 | C1[NH]C2C[NH]C1C2.c1ccccc1 | C1[NH]C2C[NH]C1C2.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 150 | null | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cccc(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].C1COCCO1>CC(C)(C)OC(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-19ca5beb727246179b7d4d2728f36d53 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cccc(Br)c1>>CC(C)(C)OC(=O)N1CC2CC1CN2c1cccc(C(F)(F)F)c1 | C1=CC(=CC(=C1)Br)C(F)(F)F.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]2[CH2:11][C@H:12]1[CH2:13][NH:14]2.Br[c:15]1[cH:16][cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]2[CH2:11][CH:12]1[CH2:13][N:14]2[c:15]1[cH:16][cH:17][cH:18][c:19]([C:2... | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cccc(Br)c1 | CC(C)(C)OC(=O)N1CC2CC1CN2c1cccc(C(F)(F)F)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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 19017c1238f901bf9ddad6509879cf8dac1766119d94f3214f1bbbb3554bb0d6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CC3CC2CN3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]1-[C:14]-[C@@H;D3;+0:15]2-[C:16]-[C:17]-1-[C:18]-[NH;D2;+0:19]-2>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]1-[C:14]-[CH;D3;+0:15]2-[C:16]-[C:17]-1-[C:1... | 92.96 | [{"value": 92.96, "product": "CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | A 50 ml round bottom equipped with stir bar was charged with binap (0.146 g, 0.23 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.088 g, 0.10 mmol) dissolved in dioxane (5 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 1-bromo-3-(trifluoromethyl)benzene (0.323 g, 1.44 mmol) followe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1[NH][C@@H]2CN[C@H]1C2.c1ccccc1 | C1[NH]C2C[NH]C1C2.c1ccccc1 | C1[NH]C2C[NH]C1C2.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 80 | null | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cccc(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].C1COCCO1>CC(C)(C)OC(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c1015abd205e430c801b5231e1cdfbf2 | Cc1ccnc(N)n1.Clc1ccnc(Cl)c1>>Cc1ccnc(Nc2cc(Cl)ccn2)n1 | C1=CN=C(C=C1Cl)Cl.CC1=NC(=NC=C1)N>>CC1=NC(=NC=C1)NC2=NC=CC(=C2)Cl | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH2:7])[n:15]1.Cl[c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]2)[n:15]1 | Cc1ccnc(N)n1.Clc1ccnc(Cl)c1 | Cc1ccnc(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.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]):[#7;a:2]:[c:3] | 57.73 | [{"value": 57.73, "product": "CC1=NC(=NC=C1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (0.607 g, 2.70 mmol) was added to 2,4-dichloropyridine (5.00 g, 33.79 mmol), 4-methylpyrimidin-2-amine (3.69 g, 33.79 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (2.346 g, 4.05 mmol) and Cesium carbonate (22.02 g, 67.57 mmol) in dioxane (150 mL) at 20ºC under nitrogen. The resulting sus... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cncnc1.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 | Cc1ccnc(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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1ccnc(Nc2cc(Cl)ccn2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-512d2d9fb0454cb39e6db5113f92b34b | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1.Oc1ccc(Br)cc1>>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(O)cc1 | C1=CC(=CC=C1O)Br.C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C2=CC=C(C=C2)O)C(=O)OC(C)(C)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][NH:14]1.Br[c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1.Oc1ccc(Br)cc1 | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(O)cc1 | CC(C)(C)[O-].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C[C@@H]1CN(CCN1C2=CC=C(C=C2)O)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.025 g, 0.12 mmol), 4-bromophenol (0.043 g, 0.25 mmol), bis(tri-t- butylphosphine)palladium(0) (6.38 mg, 0.01 mmol) and [Reactants] in THF (2 mL) was flushed with nitrogen and sealed into a microwave tube. The reaction was heated to 100 °C for 20 minutes in... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1 | 100 | null | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1.Oc1ccc(Br)cc1>CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(O)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f903bfa68e6e46fb8291b98645969acd | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I>>COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br | C1=CC(=C(C=C1C(F)(F)F)I)F.COC1=NC(=NC=C1Br)N>>COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:18][cH:19][c:20]1[Br:21].I[c:7]1[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[F:17]>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]2[F:17])[n:18][cH:19][c:20]1[Br:21] | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I | COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=COC(=C1)P(C2=CC=CO2)C3=CC=CO3.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | To a microwave vial was added a mixture of 5-bromo-4-methoxypyrimidin-2-amine (0.513 g, 2.51 mmol), diacetoxypalladium (0.055 g, 0.245 mmol), tri(furan-2-yl)phosphine (0.126 g, 0.54 mmol), 1-fluoro-2-iodo-4-(trifluoromethyl)benzene (0.98 g, 3.38 mmol) and toluene (17 mL) under inert atmosphere. The reaction mixture wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1cncnc1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=COC(=C1)P(C2=CC=CO2)C3=CC=CO3.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 90 | null | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I>C(=O)([O-])[O-].[Cs+].[Cs+].C1=COC(=C1)P(C2=CC=CO2)C3=CC=CO3.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-890c9e12800b48cca35bf6f2a67a4cca | CN1CCNCC1.COc1cc(Cl)ccc1I>>COc1cc(Cl)ccc1N1CCN(C)CC1 | COC1=C(C=CC(=C1)Cl)I.CN1CCNCC1>>CN1CCN(CC1)C2=C(C=C(C=C2)Cl)OC | [NH:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1.I[c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([Cl:6])[cH:7][cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1 | CN1CCNCC1.COc1cc(Cl)ccc1I | COc1cc(Cl)ccc1N1CCN(C)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(N2CCNCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 63.57 | [{"value": 63.57, "product": "CN1CCN(CC1)C2=C(C=C(C=C2)Cl)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium II acetate (25.09 mg, 0.11 mmol) was added to 4-chloro-1-iodo-2-methoxybenzene (300 mg, 1.12 mmol), 1-methylpiperazine (0.124 ml, 1.12 mmol), sodium 2-methylpropan-2-olate (215 mg, 2.23 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (323 mg, 0.56 mmol) in toluene (4 ml) at room temperture under nit... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HI | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | CN1CCNCC1.COc1cc(Cl)ccc1I>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>COc1cc(Cl)ccc1N1CCN(C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d1da8942a5fd4744b25120701e88bd1a | Nc1cnc2ccccc2c1.O=S(=O)(c1ccco1)N1CCc2c(ccnc2Cl)C1>>O=S(=O)(c1ccco1)N1CCc2c(ccnc2Nc2cnc3ccccc3c2)C1 | C1CN(CC2=C1C(=NC=C2)Cl)S(=O)(=O)C3=CC=CO3.C1=CC=C2C(=C1)C=C(C=N2)N>>C1CN(CC2=C1C(=NC=C2)NC3=CC4=CC=CC=C4N=C3)S(=O)(=O)C5=CC=CO5 | [NH2:18][c:19]1[cH:20][n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[cH:28]1.Cl[c:17]1[c:12]2[c:13]([cH:14][cH:15][n:16]1)[CH2:29][N:9]([S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][o:8]1)[CH2:10][CH2:11]2>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][o:8]1)[N:9]1[CH2:10][CH2:11][c:12]2[c:13]([cH:14][cH:15][n:16][c:1... | Nc1cnc2ccccc2c1.O=S(=O)(c1ccco1)N1CCc2c(ccnc2Cl)C1 | O=S(=O)(c1ccco1)N1CCc2c(ccnc2Nc2cnc3ccccc3c2)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.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | cb0553ebcb40fa01f64ed0e3f787d1a4de26cdee0812a19ff71e6e516faf141f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=S(=O)(c1ccco1)N1CCc2c(ccnc2Nc2cnc3ccccc3c2)C1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5])-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]):[#7;a:2]:[c:3] | 9.8 | [{"value": 9.8, "product": "C1CN(CC2=C1C(=NC=C2)NC3=CC4=CC=CC=C4N=C3)S(=O)(=O)C5=CC=CO5", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | The yellow residue containing 5-chloro-2-(furan-2-ylsulfonyl)-1,2,3,4-tetrahydro-2,6-naphthyridine (0.057 g, 0.19 mmol) and quinolin-3-amine (0.096 g, 0.67 mmol) from 02910-38 was dissolved in toluene (1 mL) and tert-butanol (0.170 mL). The resulting yellow solution was degassed (vacuum) and then tris(dibenzylideneacet... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cc2c(cn1)CC[NH]C2 | c1cc2c(cn1)CC[NH]C2 | c1ccoc1.c1cc2c(cn1)CC[NH]C2.c1ccc2ncccc2c1 | 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].CC(C)(C)O | 110 | null | Nc1cnc2ccccc2c1.O=S(=O)(c1ccco1)N1CCc2c(ccnc2Cl)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.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(C)(C)O>O=S(=O)(c1ccco1)N1CCc2c(c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3b22658007fa466891096d7c97ab437d | Brc1cccnc1.Nc1ccccn1>>c1ccc(Nc2cccnc2)nc1 | C1=CC(=CN=C1)Br.C1=CC=NC(=C1)N>>C1=CC=NC(=C1)NC2=CN=CC=C2 | Br[c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1.[cH:1]1[cH:2][cH:3][c:4]([NH2:5])[n:12][cH:13]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][n:10][cH:11]2)[n:12][cH:13]1 | Brc1cccnc1.Nc1ccccn1 | c1ccc(Nc2cccnc2)nc1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[c:11]:[#7;a:10]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1):[c:9] | 22.2 | [{"value": 22.2, "product": "C1=CC=NC(=C1)NC2=CN=CC=C2", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Stock solution: 0.01 mmol Pd and ligand were dissolved in 2 mL DME. 3-bromopyridine (0.482 mL, 5.00 mmol) was dissolved in DME (10 mL). To the solution was added the stock solution, and sodium tert-butoxide (0.673 g, 7.00 mmol). To the mixture was added a solution of pyridin-2-amine (0.565 g, 6.00 mmol) in DME (10 mL)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1 | HBr | CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC | 90 | null | Brc1cccnc1.Nc1ccccn1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>c1ccc(Nc2cccnc2)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2f0f980a972d4857b85fb2314cbcce6e | CC(=O)N(C)c1ccc2cc[nH]c2c1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)N(C)c1ccc2ccn(-c3cc(NC4CC4)n4ncc(C#N)c4n3)c2c1 | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)N(C)C1=CC2=C(C=C1)C=CN2>>CC(=O)N(C)C1=CC2=C(C=C1)C=CN2C3=NC4=C(C=NN4C(=C3)NC5CC5)C#N | [CH3:1][C:2](=[O:3])[N:4]([CH3:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][nH:12][c:28]2[cH:29]1.Cl[c:13]1[cH:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20]2[n:21][cH:22][c:23]([C:24]#[N:25])[c:26]2[n:27]1>>[CH3:1][C:2](=[O:3])[N:4]([CH3:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][n:12](-[c:13]3[cH:14][c:15]([NH:16][CH:... | CC(=O)N(C)c1ccc2cc[nH]c2c1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)N(C)c1ccc2ccn(-c3cc(NC4CC4)n4ncc(C#N)c4n3)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | 48025c2763e0e3b48dbecc700d7fb3bbd37c460b1e39276d3b0985ae78de45ab | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(c1)ccn2-c1cc(NC2CC2)n2nccc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[c:11]:[c:12]1:[c:13]:[c:14]:[c:15]:[nH;D2;+0:16]:1>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[n;H0;D3;+0:16]2:[c:15]:[c:14]:[c:13]:[c:12]:2:[c:11]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 15.88 | [{"value": 15.88, "product": "CC(=O)N(C)C1=CC2=C(C=C1)C=CN2C3=NC4=C(C=NN4C(=C3)NC5CC5)C#N", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In microwave tube, added 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (84mg), N-(1H-indol-6-yl)-N-methylacetamide (67 mg), Pd2(dba)3 (16 mg), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20mg) cesium carbonate(129 mg) in anhydrous DMA (0.5mL). under microwave 150C for 30 min. the... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide | null | c1ccc2[nH]ccc2c1.c1cnc2ccnn2c1 | c1ccc2cc[nH]c2c1.c1cnc2ccnn2c1 | c1ccc2cc[nH]c2c1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CC(=O)N(C)c1ccc2cc[nH]c2c1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)N(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-31892db8bbd04de79164da0921726b58 | CS(=O)(=O)Cc1cc(N)ccc1Cl.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CS(=O)(=O)Cc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1Cl | CS(=O)(=O)CC1=C(C=CC(=C1)N)Cl.C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl>>CS(=O)(=O)CC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)Cl | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][c:8]([NH2:9])[cH:25][cH:26][c:27]1[Cl:28].Cl[c:10]1[cH:11][c:12]([NH:13][CH:14]2[CH2:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]1>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][c:8]([NH:9][c:10]2[cH:11][c:12]([NH:13][CH:14]3[CH2:15][CH2:16]3)[n:1... | CS(=O)(=O)Cc1cc(N)ccc1Cl.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CS(=O)(=O)Cc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 35.03 | [{"value": 35.03, "product": "CS(=O)(=O)CC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)Cl", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (88 mg, 0.38 mmol), [Reactants], and cesium carbonate (135 mg, 0.41 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (17.24 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (21.79 mg, 0.04 mmol) were add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CS(=O)(=O)Cc1cc(N)ccc1Cl.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CS(=O)(=O)C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ac71d193208d45949ee247d7a0855249 | C1CCNC1.O=Cc1cc(F)ccc1Br>>O=Cc1cc(F)ccc1N1CCCC1 | C1=CC(=C(C=C1F)C=O)Br.C1CCNC1>>C1CCN(C1)C2=C(C=C(C=C2)F)C=O | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.Br[c:9]1[c:3]([CH:2]=[O:1])[cH:4][c:5]([F:6])[cH:7][cH:8]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | C1CCNC1.O=Cc1cc(F)ccc1Br | O=Cc1cc(F)ccc1N1CCCC1 | 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 | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:6]=[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1CCN(C1)C2=C(C=C(C=C2)F)C=O", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | To a mixture of pyrrolidine (328 mg, 3.05 mmol), 2-bromo-4-fluorobenzaldehyde (619 mg, 3.05 mmol) in toluene (10 ml) was added Cs2CO3 (2.48g, 7.62 mmol), BINAP (95 mg ) and palladium(II) acetate (35 mg) was added. The mixture was purged with Ar for 5 min, then heated at 95 oC for 4 hrs. After cooled to RT, EtOAc (30 mL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 95 | null | C1CCNC1.O=Cc1cc(F)ccc1Br>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>O=Cc1cc(F)ccc1N1CCCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bcfa3d02b4af4bc4b469f691ad0536a7 | Brc1cccc(Br)n1.O=C1COCCN1>>O=C1COCCN1c1cccc(Br)n1 | C1=CC(=NC(=C1)Br)Br.C1COCC(=O)N1>>C1COCC(=O)N1C2=NC(=CC=C2)Br | Br[c:8]1[cH:9][cH:10][cH:11][c:12]([Br:13])[n:14]1.[O:1]=[C:2]1[CH2:3][O:4][CH2:5][CH2:6][NH:7]1>>[O:1]=[C:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[c:8]1[cH:9][cH:10][cH:11][c:12]([Br:13])[n:14]1 | Brc1cccc(Br)n1.O=C1COCCN1 | O=C1COCCN1c1cccc(Br)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 4f8054226a2441fcd47c5fab339283c72cdf2181771ebd7d94028ae9fc32378c | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C1COCCN1c1ccccn1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[#8:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[C:8]-[#8:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 68.82 | [{"value": 68.82, "product": "C1COCC(=O)N1C2=NC(=CC=C2)Br", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | **_September 10 2015_** morpholin-3-one (1g, 9.89 mmol), 2,6-dibromopyridine (3.51 g, 14.84 mmol), PdOAc2 (0.222 g, 0.99 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.145 g, 1.98 mmol) and CS2CO3 (6.12 g, 18.79 mmol) in 1,4-dioxane (20 mL) were heated at 80 °C for 12 hours. **_September 11 2015_... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amide | Tertiary amide | c1ccncc1.C1COCCN1 | C1COCC[NH]1.c1ccncc1 | C1COCC[NH]1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | Brc1cccc(Br)n1.O=C1COCCN1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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=C1COCCN1c1cccc(Br)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6d8aa98c735648d3b6dca8975bbef9d2 | CC(=O)Nc1cccc(N)c1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cccc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)c1 | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=CC=CC(=C1)N>>CC(=O)NC1=CC=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:26]1.Cl[c:11]1[cH:12][c:13]([NH:14][CH:15]2[CH2:16][CH2:17]2)[n:18]2[n:19][cH:20][c:21]([C:22]#[N:23])[c:24]2[n:25]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][c:13]([NH:14][CH:15]3[CH2:16][CH2:17]3)[n:18]3[n:19][cH... | CC(=O)Nc1cccc(N)c1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cccc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 67.26 | [{"value": 67.26, "product": "CC(=O)NC1=CC=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), N-(3-aminophenyl)acetamide (51.4 mg, 0.34 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) in DMA (0.5 mL).Pd2(dba)3 (15.68 mg, 0.02 mmol) and cesium carbonate (123 m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cccc(N)c1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)Nc1cccc(Nc2... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2bde997c68344c96991dffb75b1f4b33 | Brc1ccccc1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1>>O=C(C1CC2(CCN(c3ccccc3)CC2)C1)N1CCN(C2CCC2)CC1 | C1=CC=C(C=C1)Br.C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4>>C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=C5 | Br[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[C:2]([CH:3]1[CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:15][CH2:16]2)[CH2:17]1)[N:18]1[CH2:19][CH2:20][N:21]([CH:22]2[CH2:23][CH2:24][CH2:25]2)[CH2:26][CH2:27]1>>[O:1]=[C:2]([CH:3]1[CH2:4][C:5]2([CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[CH2:15][CH2:16... | Brc1ccccc1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1 | O=C(C1CC2(CCN(c3ccccc3)CC2)C1)N1CCN(C2CCC2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e9241c29e03e8a4c10117d250ffe8cebe005189c2a9282e6952ec9ded65ebe40 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(C1CC2(CCN(c3ccccc3)CC2)C1)N1CCN(C2CCC2)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] | 46.78 | [{"value": 46.78, "product": "C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=C5", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | cesium carbonate (123 mg, 0.38 mmol) was added to a solution of (4-cyclobutylpiperazin-1-yl)(7-azaspiro[3.5]nonan-2-yl)methanone (100 mg, 0.34 mmol), PdOAc2 (7.70 mg, 0.03 mmol), BINAP (42.7 mg, 0.07 mmol) and bromobenzene (56.6 mg, 0.36 mmol) in toluene (5 mL). The reaction mixture was heated to 110°C for 18hrs. The r... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CC2(C1)CCNCC2 | C1CC2(C1)CC[NH]CC2.c1ccccc1 | C1CC2(C1)CC[NH]CC2.c1ccccc1.C1C[NH]CC[NH]1.C1CCC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | Brc1ccccc1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>O=C(C1CC2(CCN(c3ccccc3)CC2)C1)N1CCN(C2CCC2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6ca842b2903f47c19f42752e7a96ea52 | CC(=O)Nc1cc(N)ccc1N1CC[C@H](N(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CC[C@H](N(C)C)C1 | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N2CC[C@@H](C2)N(C)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CC[C@@H](C5)N(C)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]1[CH2:28][CH2:29][C@H:30]([N:31]([CH3:32])[CH3:33])[CH2:34]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](N(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CC[C@H](N(C)C)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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(N4CCCC4)cc3)cc(NC3CC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 36.66 | [{"value": 36.66, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CC[C@@H](C5)N(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (100mg, 0.43 mmol), [Reactants], and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (24.76 mg, 0.04 mmol) in DMA (1.0 mL).Pd2(dba)3 (19.60 mg, 0.02 mmol) and cesium carbonate (279 mg, 0.86 mmol) were added. degassed,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1.C1CC[NH]C1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1N1CC[C@H](N(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4ba8493a4d7f4107b8a89b01cdd11168 | CC(C)(C)OC(N)=O.Cc1cc(CO)cc(Cl)n1>>Cc1cc(CO)cc(NC(=O)OC(C)(C)C)n1 | CC1=CC(=CC(=N1)Cl)CO.CC(C)(C)OC(=O)N>>CC1=CC(=CC(=N1)NC(=O)OC(C)(C)C)CO | [NH2:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].Cl[c:8]1[cH:7][c:4]([CH2:5][OH:6])[cH:3][c:2]([CH3:1])[n:17]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][OH:6])[cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[n:17]1 | CC(C)(C)OC(N)=O.Cc1cc(CO)cc(Cl)n1 | Cc1cc(CO)cc(NC(=O)OC(C)(C)C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | ed01b145192f9cffb3f3553513f8bbd15ca4f246fc1ccc0dad392a1f0f7069ce | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:13])-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CC1=CC(=CC(=N1)NC(=O)OC(C)(C)C)CO", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | A 2.0-5.0 mL microwave vial was charged with XANTPHOS (14.66 mg, 0.03 mmol), Pd2(dba)3 (29.1 mg, 0.03 mmol), CESIUM CARBONATE (155 mg, 0.48 mmol),(2-chloro-6-methylpyridin-4-yl)methanol (50 mg, 0.32 mmol), tert-butyl carbamate (44.6 mg, 0.38 mmol) and dioxane (3 mL). The reaction mixture was degassed for 2 minutes with... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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 | CC(C)(C)OC(N)=O.Cc1cc(CO)cc(Cl)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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>Cc1cc(CO)cc(NC(=O)OC(C)(C)C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a20b5a194b7e441a86818aba8bf8e5b1 | CC(=O)Nc1cc(N)ccc1C(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C(C)C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(C)C1=C(C=C(C=C1)N)NC(=O)C>>CC(C)C1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[CH:27]([CH3:28])[CH3:29].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]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]... | CC(=O)Nc1cc(N)ccc1C(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C(C)C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 10.29 | [{"value": 10.29, "product": "CC(C)C1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | In a 5 mL microwave reactor vial was charged with 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.070 g, 0.30 mmol), N-(5-amino-2-isopropylphenyl)acetamide (0.058 g, 0.30 mmol), Pd2(dba)3 (0.014 g, 0.01 mmol), Pd2(dba)3 (0.014 g, 0.01 mmol) and cesium carbonate (0.293 g, 0.90 mmol), the vessel ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 140 | null | CC(=O)Nc1cc(N)ccc1C(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)Nc1cc(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-db902466b4d9464996daff204ba92575 | Cc1csc(N)n1.O=C1OCCCN1c1cccc(Br)n1>>Cc1csc(Nc2cccc(N3CCCOC3=O)n2)n1 | C1CN(C(=O)OC1)C2=NC(=CC=C2)Br.CC1=CSC(=N1)N>>CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:20]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][CH2:15][O:16][C:17]2=[O:18])[n:19]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][CH2:15][O:16][C:17]3=[O:18])[n:19]2)[n:20]1 | Cc1csc(N)n1.O=C1OCCCN1c1cccc(Br)n1 | Cc1csc(Nc2cccc(N3CCCOC3=O)n2)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.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1OCCCN1c1cccc(Nc2nccs2)n1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1):[c:4]:[c:5] | 43.95 | [{"value": 43.95, "product": "CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | **_September 21 2015_** 4-methylthiazol-2-amine (85 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.1 mg, 0.07 mmol) and cesium carbonate (291 mg, 0.89 mmol) in ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cscn1.c1ccncc1.C1C[NH]COC1 | 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.[Pd].CC1=CC=CC=C1 | 120 | null | Cc1csc(N)n1.O=C1OCCCN1c1cccc(Br)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.[Pd].CC1=CC=CC=C1>Cc1csc(Nc2cccc(N3CCCOC3=O)n2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-afb4a5c3ac0340ae885e81e91d7c667d | Cc1csc(N)n1.O=C1OCCCN1c1cccc(Br)n1>>Cc1csc(Nc2cccc(N3CCCOC3=O)n2)n1 | C1CN(C(=O)OC1)C2=NC(=CC=C2)Br.CC1=CSC(=N1)N>>CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:20]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][CH2:15][O:16][C:17]2=[O:18])[n:19]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][CH2:15][O:16][C:17]3=[O:18])[n:19]2)[n:20]1 | Cc1csc(N)n1.O=C1OCCCN1c1cccc(Br)n1 | Cc1csc(Nc2cccc(N3CCCOC3=O)n2)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.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1OCCCN1c1cccc(Nc2nccs2)n1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1):[c:4]:[c:5] | 57.15 | [{"value": 57.15, "product": "CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | **_September 28 2015_** 4-methylthiazol-2-amine (300 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (152 mg, 0.26 mmol) and cesium carbonate (1027 mg, 3.15 mmol) in... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cscn1.c1ccncc1.C1C[NH]COC1 | 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.[Pd].CC1=CC=CC=C1 | 115 | null | Cc1csc(N)n1.O=C1OCCCN1c1cccc(Br)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.[Pd].CC1=CC=CC=C1>Cc1csc(Nc2cccc(N3CCCOC3=O)n2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b790a1db0b324eea8d1b75eaa501512c | C1CNCCN1.Cc1ccc(Nc2c(C#N)nnc3cc(Br)ccc23)c(F)c1>>Cc1ccc(Nc2c(C#N)nnc3cc(N4CCNCC4)ccc23)c(F)c1 | CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)Br)C#N)F.C1CNCCN1>>CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)C#N)F | [NH:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1.Br[c:15]1[cH:14][c:13]2[n:12][n:11][c:8]([C:9]#[N:10])[c:7]([NH:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:27][c:25]3[F:26])[c:24]2[cH:23][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[c:8]([C:9]#[N:10])[n:11][n:12][c:13]3[cH:14][c:15]([N:16]4[CH2:17][CH2:18][NH:19][CH... | C1CNCCN1.Cc1ccc(Nc2c(C#N)nnc3cc(Br)ccc23)c(F)c1 | Cc1ccc(Nc2c(C#N)nnc3cc(N4CCNCC4)ccc23)c(F)c1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8185b9142df247f6ef423eb18dbdbdcc7289e27f788ad1f4bd91d4d98e7c7565 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2cnnc3cc(N4CCNCC4)ccc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[#7;a:5]):[c:6]:[c:7]:[c:8]:1.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7;a:5]:[#7;a:4]:[c:3]1:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:8]:[c:7]:[c:6]:1 | 50.66 | [{"value": 50.66, "product": "CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)C#N)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A 1L flask was charged with 7-bromo-4-(2-fluoro-4-methylphenylamino)cinnoline-3-carbonitrile (3.93 g, 11.00 mmol), Piperazine (3.88 ml, 49.51 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.806 g, 0.88 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.787 g, 1.65 mmol) and Sodium tert-butoxide... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2nnccc2c1 | c1ccc2nnccc2c1.C1C[NH]CCN1 | c1ccccc1.c1ccc2nnccc2c1.C1C[NH]CCN1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 100 | null | C1CNCCN1.Cc1ccc(Nc2c(C#N)nnc3cc(Br)ccc23)c(F)c1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>Cc1ccc(Nc2c(C#N)nnc3cc(N4CCNCC4)ccc23)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-05542745a3df403aa88ae927045679bd | C1CNCCN1.Cc1ccc(Nc2c(C#N)nnc3cc(Br)ccc23)c(F)c1>>Cc1ccc(Nc2c(C#N)nnc3cc(N4CCNCC4)ccc23)c(F)c1 | CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)Br)C#N)F.C1CNCCN1>>CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)C#N)F | [NH:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1.Br[c:15]1[cH:14][c:13]2[n:12][n:11][c:8]([C:9]#[N:10])[c:7]([NH:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:27][c:25]3[F:26])[c:24]2[cH:23][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[c:8]([C:9]#[N:10])[n:11][n:12][c:13]3[cH:14][c:15]([N:16]4[CH2:17][CH2:18][NH:19][CH... | C1CNCCN1.Cc1ccc(Nc2c(C#N)nnc3cc(Br)ccc23)c(F)c1 | Cc1ccc(Nc2c(C#N)nnc3cc(N4CCNCC4)ccc23)c(F)c1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8185b9142df247f6ef423eb18dbdbdcc7289e27f788ad1f4bd91d4d98e7c7565 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2cnnc3cc(N4CCNCC4)ccc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[#7;a:5]):[c:6]:[c:7]:[c:8]:1.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7;a:5]:[#7;a:4]:[c:3]1:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:8]:[c:7]:[c:6]:1 | 84.7 | [{"value": 84.7, "product": "CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)C#N)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A 100 mL flask was charged with 7-bromo-4-(2-fluoro-4-methylphenylamino)cinnoline-3-carbonitrile (0.64 g, 1.79 mmol), Piperazine (0.631 ml, 8.06 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.131 g, 0.14 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso- propyl-1,1'-biphenyl (0.128 g, 0.27 mmol) and Sodium tert-buto... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2nnccc2c1 | c1ccc2nnccc2c1.C1C[NH]CCN1 | c1ccccc1.c1ccc2nnccc2c1.C1C[NH]CCN1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 100 | null | C1CNCCN1.Cc1ccc(Nc2c(C#N)nnc3cc(Br)ccc23)c(F)c1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>Cc1ccc(Nc2c(C#N)nnc3cc(N4CCNCC4)ccc23)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f20b22261a054781bd10039c93816deb | Cc1cc(N)nc(C)n1.Clc1ccnc(Cl)c1>>Cc1cc(Nc2cc(Cl)ccn2)nc(C)n1 | C1=CN=C(C=C1Cl)Cl.CC1=CC(=NC(=N1)C)N>>CC1=CC(=NC(=N1)C)NC2=NC=CC(=C2)Cl | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:13][c:14]([CH3:15])[n:16]1.Cl[c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]2)[n:13][c:14]([CH3:15])[n:16]1 | Cc1cc(N)nc(C)n1.Clc1ccnc(Cl)c1 | Cc1cc(Nc2cc(Cl)ccn2)nc(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)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]:[#7;a:10]:[c:11]:[c:12]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1):[c:4]:[c:5] | 61.24 | [{"value": 61.24, "product": "CC1=CC(=NC(=N1)C)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (0.607 g, 2.70 mmol) was added to 2,4-dichloropyridine (5.00 g, 33.79 mmol), 2,6-dimethylpyrimidin-4-amine (4.16 g, 33.79 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (2.346 g, 4.05 mmol) and Cesium carbonate (22.02 g, 67.57 mmol) in dioxane (150 mL) at 20ºC under nitrogen. The resulting... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cncnc1.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 | Cc1cc(N)nc(C)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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1cc(Nc2cc(Cl)ccn2)nc(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5c5d7fac90d14102bcad7fe6bdad56a8 | Fc1ccc(Br)c(Cl)c1.O=C1CCNCC1>>O=C1CCN(c2ccc(F)cc2Cl)CC1 | C1=CC(=C(C=C1F)Cl)Br.C1CNCCC1=O>>C1CN(CCC1=O)C2=C(C=C(C=C2)F)Cl | Br[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[Cl:13].[O:1]=[C:2]1[CH2:3][CH2:4][NH:5][CH2:14][CH2:15]1>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]2[Cl:13])[CH2:14][CH2:15]1 | Fc1ccc(Br)c(Cl)c1.O=C1CCNCC1 | O=C1CCN(c2ccc(F)cc2Cl)CC1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C1CCN(c2ccccc2)CC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[O;D1;H0:7]=[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8](=[O;D1;H0:7])-[C:13]-[C:12]-1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1CN(CCC1=O)C2=C(C=C(C=C2)F)Cl", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | To a round bottom flask was added palladium(II) acetate (0.012 g, 0.06 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.026 g, 0.06 mmol), and sodium tert-butoxide (0.213 g, 2.21 mmol). Added 5 mL toluene/t-butanol mix and purged with nitrogen. Added piperidin-4-one (0.15 g, 1.11 mmol), in 3 mL tol/t... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].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 | Fc1ccc(Br)c(Cl)c1.O=C1CCNCC1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>O=C1CCN(c2ccc(F)cc2Cl)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d7f47b4e3d2047bbb6f27fb595bc1873 | Brc1ccccn1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1>>O=C(C1CC2(CCN(c3ccccn3)CC2)C1)N1CCN(C2CCC2)CC1 | C1=CC=NC(=C1)Br.C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4>>C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=N5 | Br[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1.[O:1]=[C:2]([CH:3]1[CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:15][CH2:16]2)[CH2:17]1)[N:18]1[CH2:19][CH2:20][N:21]([CH:22]2[CH2:23][CH2:24][CH2:25]2)[CH2:26][CH2:27]1>>[O:1]=[C:2]([CH:3]1[CH2:4][C:5]2([CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][cH:12][cH:13][n:14]3)[CH2:15][CH2:16]2... | Brc1ccccn1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1 | O=C(C1CC2(CCN(c3ccccn3)CC2)C1)N1CCN(C2CCC2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75377ac1e22f3738296927ba29d3f942a20b96a4f93f0c857f61f0541f1f6447 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(C1CC2(CCN(c3ccccn3)CC2)C1)N1CCN(C2CCC2)CC1 | 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] | 42.78 | [{"value": 42.78, "product": "C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=N5", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | cesium carbonate (123 mg, 0.38 mmol) was added to a solution of (4-cyclobutylpiperazin-1-yl)(7-azaspiro[3.5]nonan-2-yl)methanone (100 mg, 0.34 mmol), PdOAc2 (7.70 mg, 0.03 mmol), BINAP (42.7 mg, 0.07 mmol) and 2-bromopyridine (56.9 mg, 0.36 mmol) in toluene (2 mL). The reaction mixture was heated to 110°C for 18hrs. Th... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CC2(C1)CCNCC2 | C1CC2(C1)CC[NH]CC2.c1ccncc1 | C1CC2(C1)CC[NH]CC2.c1ccncc1.C1C[NH]CC[NH]1.C1CCC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | Brc1ccccn1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>O=C(C1CC2(CCN(c3ccccn3)CC2)C1)N1CCN(C2CCC2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1a02b93898c84c3a8a0ec8185fbf85c5 | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCN(C)C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N(C)CCN(C)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]([CH3:28])[CH2:29][CH2:30][N:31]([CH3:32])[CH3:33].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]([NH:12][... | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCN(C)C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 22.45 | [{"value": 22.45, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (200 mg, 0.86 mmol), N-(5-amino-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acetamide (214 mg, 0.86 mmol), and cesium carbonate (363 mg, 1.11 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (39.2 mg, 0.04 mmol) and (9,9-dimeth... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-01bb5c09bf964bc095ad839c85efa1ae | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCN(C)C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N(C)CCN(C)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]([CH3:28])[CH2:29][CH2:30][N:31]([CH3:32])[CH3:33].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]([NH:12][... | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCN(C)C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 29.37 | [{"value": 29.37, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), [Reactants], and cesium carbonate (145 mg, 0.45 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (15.68 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) were add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1N(C)CCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-56f044d6c15d456091eeeb1952199469 | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[CH3:27].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]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]3[n:17][cH:18][c:... | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 18.09 | [{"value": 18.09, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (400 mg, 1.71 mmol), N-(5-amino-2-methylphenyl)acetamide (281 mg, 1.71 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (99 mg, 0.17 mmol) in DMA (0.5 mL).Pd2(dba)3 (78 mg, 0.09 mmol) and cesium carbonate (11... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b36688f4348242fd9c6b24fe5e96aaf0 | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[CH3:27].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]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]3[n:17][cH:18][c:... | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 18.59 | [{"value": 18.59, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), N-(5-amino-2-methylphenyl)acetamide (56.2 mg, 0.34 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) in DMA (0.5 mL).Pd2(dba)3 (15.68 mg, 0.02 mmol) and cesium carbona... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9f120d17ec3047d5829b45c5b320d657 | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[CH3:27].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]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]3[n:17][cH:18][c:... | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 22.63 | [{"value": 22.63, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (500 mg, 2.14 mmol), N-(5-amino-2-methylphenyl)acetamide (351 mg, 2.14 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (124 mg, 0.21 mmol) in DMA (2.5 mL).Pd2(dba)3 (98 mg, 0.11 mmol) and cesium carbonate (1... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | 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].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9d52138831044592b5c7c5511d53f49c | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[CH3:27].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]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]3[n:17][cH:18][c:... | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C | CC(C)(C)[O-].[Na+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 0 | [{"value": 0.0, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | In a 25 mL round-bottomed flask (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (40 mg, 0.17 mmol), Pd2(dba)3 (7.84 mg, 8.56 µmol), and [Reactants] in DMA (1.5 mL) ([VOLUME]) to give a black suspension.[Reactants] and N-(5-amino-2-methylphenyl)acetamide (28.1 mg, 0.17 mmol) were added. ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | HCl | CC(C)(C)[O-].[Na+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 120 | null | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>CC(C)(C)[O-].[Na+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8f20cf3b966d4cdd9e1178539b8e969e | CS(=O)(=O)c1ccc(Br)cc1.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>>C[C@@H]1CN(c2ccc(S(C)(=O)=O)cc2)CCN1C(=O)OC(C)(C)C | CS(=O)(=O)C1=CC=C(C=C1)Br.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC=C(C=C2)S(=O)(=O)C | Br[c:5]1[cH:6][cH:7][c:8]([S:9]([CH3:10])(=[O:11])=[O:12])[cH:13][cH:14]1.[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:15][CH2:16][N:17]1[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([S:9]([CH3:10])(=[O:11])=[O:12])[cH:13][cH:14]2)[CH2:15][CH2:16][N:17]1[C:18](=[O:19... | CS(=O)(=O)c1ccc(Br)cc1.C[C@@H]1CNCCN1C(=O)OC(C)(C)C | C[C@@H]1CN(c2ccc(S(C)(=O)=O)cc2)CCN1C(=O)OC(C)(C)C | CC(C)(C)[O-].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC=C(C=C2)S(=O)(=O)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 13-May-09 10:32:28 +0100 1-bromo-4-(methylsulfonyl)benzene (515 mg, 2.13 mmol), (R)-tert-butyl 2-methylpiperazine-1-carboxylate (426 mg, 2.13 mmol) and BIS(TRI-T- BUTYLPHOSPHINE)PALLADIUM(0) (54.3 mg, 0.11 mmol) and potassium 2-methylpropan-2-olate (352 mg, 2.98 mmol) were suspended in dioxane (10 mL) and heated to 90... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1COCCO1 | 100 | null | CS(=O)(=O)c1ccc(Br)cc1.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1COCCO1>C[C@@H]1CN(c2ccc(S(C)(=O)=O)cc2)CCN1C(=O)OC(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-80eaa5d6e27d4cf78d75715b3843cadc | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1ccc(Br)cc1Cl>>CC(C)(C)OC(=O)N1CCN(c2ccc(C#N)c(Cl)c2)CC1 | C1=CC(=C(C=C1Br)Cl)C#N.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C#N)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:21][CH2:22]1.Br[c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[c:18]([Cl:19])[cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([C:16]#[N:17])[c:18]([Cl:19])[cH:20]2)[CH2:21][CH2:22... | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1ccc(Br)cc1Cl | CC(C)(C)OC(=O)N1CCN(c2ccc(C#N)c(Cl)c2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 47.09 | [{"value": 47.09, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C#N)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | In a 250 mL round-bottomed dried flask , diacetoxypalladium (0.036 g, 0.16 mmol) was treated with 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.195 g, 0.31 mmol) under nitrogen in toluene (35 mL). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxyla... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1ccc(Br)cc1Cl>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2ccc(C#N)c(Cl)c2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-411cbd769b2f48f9a0808a7d2919db15 | C/C=C(/c1ccc(C)cc1)N(C(=O)NC)c1ccc(OC)cc1.Cc1cccc(Br)n1>>C/C=C(/c1ccc(C)cc1)N(C(=O)N(C)c1cccc(C)n1)c1ccc(OC)cc1 | CC1=NC(=CC=C1)Br.C/C=C(/C1=CC=C(C=C1)C)\N(C2=CC=C(C=C2)OC)C(=O)NC>>C/C=C(/C1=CC=C(C=C1)C)\N(C2=CC=C(C=C2)OC)C(=O)N(C)C3=CC=CC(=N3)C | [CH3:1]/[CH:2]=[C:3](/[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:9][cH:10]1)[N:11]([C:12](=[O:13])[NH:14][CH3:15])[c:23]1[cH:24][cH:25][c:26]([O:27][CH3:28])[cH:29][cH:30]1.Br[c:16]1[cH:17][cH:18][cH:19][c:20]([CH3:21])[n:22]1>>[CH3:1]/[CH:2]=[C:3](/[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:9][cH:10]1)[N:11]([C:12](=[O:13])[N:14]([... | C/C=C(/c1ccc(C)cc1)N(C(=O)NC)c1ccc(OC)cc1.Cc1cccc(Br)n1 | C/C=C(/c1ccc(C)cc1)N(C(=O)N(C)c1cccc(C)n1)c1ccc(OC)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 | Goldberg coupling | c3e9b5e88e70ea085ab3c4bfcb036b7f23a5295a2a4a0ed37fb9d51f344d671b | 4c2887f4c8bf37383c1643fa8c0d6572d6d560713e2566c5529210af209aa988 | [CH]=C(c1ccccc1)N(C(=O)Nc1ccccn1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#7:10](-[c:11])/[C:12](-[c:13])=[C:14]\[C;D1;H3:15]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C:8](=[O;D1;H0:9])-[#7:10](-[c:11])/[C:12](-[c:13])=[C:14]\[C;D1;H3:15])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 84.95 | [{"value": 84.95, "product": "C/C=C(/C1=CC=C(C=C1)C)\\N(C2=CC=C(C=C2)OC)C(=O)N(C)C3=CC=CC(=N3)C", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | (Z)-1-(4-methoxyphenyl)-3-methyl-1-(1-p-tolylprop-1-enyl)urea (0.17200 g, 0.55 mmol),2-bromo-6-methylpyridine (0.126 ml, 1.11 mmol),SODIUM TERT-BUTOXIDE (0.160 g, 1.66 mmol),XANTPHOS (0.032 g, 0.06 mmol) and Pd2(dba)3 (0.025 g, 0.03 mmol) were dissolved intoluene (5.42 ml) and sparged under nitrogen for 15minutes . The... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Urea | Urea | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | C/C=C(/c1ccc(C)cc1)N(C(=O)NC)c1ccc(OC)cc1.Cc1cccc(Br)n1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>C/C=C(/c1ccc(C)cc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7d21d2aa9b9646bf85b8f593faa79359 | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)c(F)cc1C1CC1 | C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=CC(=C(C=C1C2CC2)F)N>>CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:25]([F:26])[cH:27][c:28]1[CH:29]1[CH2:30][CH2:31]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][O:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]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]([NH:12][CH:13]3[CH2:14][O:... | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)c(F)cc1C1CC1 | 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 | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(C4CC4)cc3)cc(NC3COC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 23.91 | [{"value": 23.91, "product": "CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | dioxane (4 mL) was adde to the mixture of N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (100 mg, 0.48 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (132 mg, 0.53 mmol),cesium carbonate (469 mg, 1.44 mmol), Pd2(dba)3 (44.0 mg, 0.05 mmol), di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-y... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1COC1.c1cnc2ccnn2c1.C1CC1 | 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 | 140 | null | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)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].C1COCCO1>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f2ae1a21bc9f45a9af6696711f426a7c | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)c(F)cc1C1CC1 | C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=CC(=C(C=C1C2CC2)F)N>>CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:25]([F:26])[cH:27][c:28]1[CH:29]1[CH2:30][CH2:31]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][O:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]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]([NH:12][CH:13]3[CH2:14][O:... | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)c(F)cc1C1CC1 | 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 | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(C4CC4)cc3)cc(NC3COC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 11.85 | [{"value": 11.85, "product": "CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | The mixture of N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (54.2 mg, 0.26 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (50.0 mg, 0.20 mmol), cesium carbonate (196 mg, 0.60 mmol), Pd2(dba)3 (18.34 mg, 0.02 mmol) and di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (17.01 m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1COC1.c1cnc2ccnn2c1.C1CC1 | 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 | 130 | null | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)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].C1COCCO1>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bfef1bef76ff43f7a429af888b0d1628 | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)c(F)cc1C1CC1 | C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=CC(=C(C=C1C2CC2)F)N>>CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:25]([F:26])[cH:27][c:28]1[CH:29]1[CH2:30][CH2:31]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][O:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]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]([NH:12][CH:13]3[CH2:14][O:... | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)c(F)cc1C1CC1 | 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] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(C4CC4)cc3)cc(NC3COC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 3.55 | [{"value": 3.55, "product": "CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N", "details": "", "is_desired": true}] | 145 | CELSIUS | null | null | In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (0.167 g, 0.80 mmol), Pd2dba3 (0.037 g, 0.04 mmol),5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.200 g, 0.80 mmol),di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.034 g, 0.08... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1COC1.c1cnc2ccnn2c1.C1CC1 | 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].CC(=O)N(C)C | 145 | null | CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)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].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3nc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-72695457b0814d8bbec66d3f30d9e87c | Cc1csc(N)n1.O=C(O)c1cccc(Br)n1>>Cc1csc(Nc2cccc(C(=O)O)n2)n1 | C1=CC(=NC(=C1)Br)C(=O)O.CC1=CSC(=N1)N>>CC1=CSC(=N1)NC2=CC=CC(=N2)C(=O)O | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:16]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[n:15]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[n:15]2)[n:16]1 | Cc1csc(N)n1.O=C(O)c1cccc(Br)n1 | Cc1csc(Nc2cccc(C(=O)O)n2)n1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccs2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1):[c:7]:[c:8] | 0 | [{"value": 0.0, "product": "CC1=CSC(=N1)NC2=CC=CC(=N2)C(=O)O", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | _The aim of this reaction is to synthesize material to check some ideas for route development and see if 'normal' Buchwald conditions is applicable here. IPC.s were taken and the reaction was monitored either by LCMS or HNMR (a crude sample dissolved in DMSO)._ 19/11-2015 14:00 A dried 250 mL rb-flask under nitrogen... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cscn1.c1ccncc1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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 | Cc1csc(N)n1.O=C(O)c1cccc(Br)n1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1csc(Nc2cccc(C(=O)O)n2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7e7ab408c09a4157a27808089c5163bc | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cccc(Cl)n1>>CC(C)(C)OC(=O)N1CCN(c2cccc(C(F)(F)F)n2)CC1 | C1=CC(=NC(=C1)Cl)C(F)(F)F.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:22][CH2:23]1.Cl[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[n:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[n:21]2)[CH... | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cccc(Cl)n1 | CC(C)(C)OC(=O)N1CCN(c2cccc(C(F)(F)F)n2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[#7;a:2]:[c:3] | 51.68 | [{"value": 51.68, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | A 20 mL microwave vial was charged with 2-chloro-6-(trifluoromethyl)pyridine (860 mg, 4.74 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (295 mg, 0.47 mmol), Sodium tert-butoxide (546 mg, 5.68 mmol), tert-butyl piperazine-1-carboxylate (882 mg, 4.74 mmol) and a mixture of toluene (25 mL) and DMF (5 mL). The re... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | 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 | 105 | null | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cccc(Cl)n1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a2881fa75a3a4ea0adb4ff5901bc0b55 | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cccc(Cl)n1>>CC(C)(C)OC(=O)N1CCN(c2cccc(C(F)(F)F)n2)CC1 | C1=CC(=NC(=C1)Cl)C(F)(F)F.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:22][CH2:23]1.Cl[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[n:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[n:21]2)[CH... | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cccc(Cl)n1 | CC(C)(C)OC(=O)N1CCN(c2cccc(C(F)(F)F)n2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[#7;a:2]:[c:3] | 46.38 | [{"value": 46.38, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | A 2.0-5.0 mL microwave vial was charged with 2-chloro-6-(trifluoromethyl)pyridine (86 mg, 0.47 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (29.5 mg, 0.05 mmol), Sodium tert-butoxide (54.6 mg, 0.57 mmol), tert-butyl piperazine-1-carboxylate (88 mg, 0.47 mmol) and a mixture of toluene (2.5 mL) and DMF (.5 mL).... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | 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 | 105 | null | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cccc(Cl)n1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b0d4d24d68264e0ba39e9d5692455d36 | CC(C)(C)OC(=O)N1CC2CNCC2C1.COc1cc(Br)ccc1Cl>>COc1cc(N2CC3CN(C(=O)OC(C)(C)C)CC3C2)ccc1Cl | COC1=C(C=CC(=C1)Br)Cl.CC(C)(C)OC(=O)N1CC2CNCC2C1>>CC(C)(C)OC(=O)N1CC2CN(CC2C1)C3=CC(=C(C=C3)Cl)OC | [NH:6]1[CH2:7][CH:8]2[CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH:19]2[CH2:20]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:23]([Cl:24])[cH:22][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH:8]3[CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH:19]3[C... | CC(C)(C)OC(=O)N1CC2CNCC2C1.COc1cc(Br)ccc1Cl | COc1cc(N2CC3CN(C(=O)OC(C)(C)C)CC3C2)ccc1Cl | 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 | d49e74fca87b39b3badcfb69cd11ef53eec408f12d53f25178f7dc6b783a0fb0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CC3CNCC3C2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]1-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[C:10]-[C:9]-1):[c:4]:[c:5] | 64.57 | [{"value": 64.57, "product": "CC(C)(C)OC(=O)N1CC2CN(CC2C1)C3=CC(=C(C=C3)Cl)OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A mixture of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (205 mg, 0.97 mmol), 5-Bromo-2-chloroanisole (235 mg, 1.06 mmol), Sodium tert- butoxide (130 mg, 1.35 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (30.1 mg, 0.05 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (44.2 mg, 0.05 mmol) in ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1[NH]CC2CNCC12.c1ccccc1 | c1ccccc1.C1[NH]CC2C[NH]CC12 | c1ccccc1.C1[NH]CC2C[NH]CC12 | 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 | CC(C)(C)OC(=O)N1CC2CNCC2C1.COc1cc(Br)ccc1Cl>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1cc(N2CC3CN(C(=O... |
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