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-22a60e15dfdd4a64952f48510c12252f | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.COc1cccc(Br)c1>>COc1cccc(N2CCCC2c2cc(C(=O)N(C)C)cc3c(=O)cc(N4CCOCC4)oc23)c1 | COC1=CC(=CC=C1)Br.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)OC)OC(=CC2=O)N5CCOCC5 | [NH:8]1[CH2:9][CH2:10][CH2:11][CH:12]1[c:13]1[cH:14][c:15]([C:16](=[O:17])[N:18]([CH3:19])[CH3:20])[cH:21][c:22]2[c:23](=[O:24])[cH:25][c:26]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[o:33][c:34]12.Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:1... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.COc1cccc(Br)c1 | COc1cccc(N2CCCC2c2cc(C(=O)N(C)C)cc3c(=O)cc(N4CCOCC4)oc23)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 27.52 | [{"value": 27.52, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)OC)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.93 mg, 0.02 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (130 mg, 0.35 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.25 mg, 0.03 mmol), 1-bromo-3-methoxybenzene (0.055 ml, 0.44 mmol) and cesium carbonat... | 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.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.COc1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cccc(N2CCCC2c2cc(C(=O)N(C)C)cc3c(=O)cc(N4CCOCC4)oc23)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2c85deae4d144af0a18fb548e5e9eabd | Nc1ccccc1.O=[N+]([O-])c1ccccc1Br>>O=[N+]([O-])c1ccccc1Nc1ccccc1 | C1=CC=C(C(=C1)[N+](=O)[O-])Br.C1=CC=C(C=C1)N>>C1=CC=C(C=C1)NC2=CC=CC=C2[N+](=O)[O-] | [NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.Br[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | Nc1ccccc1.O=[N+]([O-])c1ccccc1Br | O=[N+]([O-])c1ccccc1Nc1ccccc1 | 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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | 84.87 | [{"value": 84.87, "product": "C1=CC=C(C=C1)NC2=CC=CC=C2[N+](=O)[O-]", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A 200 mL roundbottom flask was charged with 1-bromo-2-nitrobenzene (Alfa Aesar; 2.10 g, 10.40 mmol), Pd2(dba)3 (Aldrich; 119.6 mg, 2.5 mol%), racemic BINAP (Strem; 197.8 mg, 3.1 mol%), and cesium carbonate (Aldrich; 4.87 g, 14.95 mmol). The flask was evacuated and backfilled with N2 (3x), and then anhydrous toluene (20... | 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+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | Nc1ccccc1.O=[N+]([O-])c1ccccc1Br>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>O=[N+]([O-])c1ccccc1N... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d9ed07514588414a96d99512916e6b2b | COc1nc(N)ccc1-n1cnc(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1>>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-n1cnc(C)c1 | CC1=CSC(=N1)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=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=NC(=CS5)C)C)C=C3)OC | [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][c:17]([CH3:18])[cH:19][s:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13]... | COc1nc(N)ccc1-n1cnc(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1 | COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)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] | 10.63 | [{"value": 10.63, "product": "CC1=CN(C=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=NC(=CS5)C)C)C=C3)OC", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To 8-chloro-4-methyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (120 mg, 0.41 mmol) in DME (3 mL) were 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (83 mg, 0.41 mmol), cesium carbonate (198 mg, 0.61 mmol), 2-(Dicyclohexylphosphino)biphenyl (14.22 mg, 0.04 mmol) and Palladium acetat... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccncc1.c1cnc2c(c1)C[NH]CCO2.c1cscn1.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 | 110 | null | COc1nc(N)ccc1-n1cnc(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-53ade929d04044c58b3188ce55627881 | COc1nc(N)ccc1-n1cnc(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1>>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-n1cnc(C)c1 | CC1=CSC(=N1)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=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=NC(=CS5)C)C)C=C3)OC | [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][c:17]([CH3:18])[cH:19][s:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13]... | COc1nc(N)ccc1-n1cnc(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1 | COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)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] | 20.42 | [{"value": 20.42, "product": "CC1=CN(C=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=NC(=CS5)C)C)C=C3)OC", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To 8-chloro-4-methyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (50 mg, 0.17 mmol) in DME (3 mL) were 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (34.5 mg, 0.17 mmol), cesium carbonate (83 mg, 0.25 mmol), 2-(Dicyclohexylphosphino)biphenyl (5.92 mg, 0.02 mmol) and Palladium acetate... | 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 | 110 | null | COc1nc(N)ccc1-n1cnc(C)c1.Cc1csc(C2CN(C)Cc3ccc(Cl)nc3O2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b45fc3e4fad4439cafccda47ed5c0991 | C1COCCN1.COC(=O)c1cc(Br)ccc1I>>COC(=O)c1cc(Br)ccc1N1CCOCC1 | COC(=O)C1=C(C=CC(=C1)Br)I.C1COCCN1>>COC(=O)C1=C(C=CC(=C1)Br)N2CCOCC2 | [NH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1.I[c:11]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][c:7]([Br:8])[cH:9][cH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1 | C1COCCN1.COC(=O)c1cc(Br)ccc1I | COC(=O)c1cc(Br)ccc1N1CCOCC1 | 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] | COCCOC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-1):[c:2]:[c:3] | 17.85 | [{"value": 17.85, "product": "COC(=O)C1=C(C=CC(=C1)Br)N2CCOCC2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a solution of methyl 5-bromo-2-iodobenzoate (2.1 g, 6.16 mmol) in DME (15 mL) were morpholine (0.593 mL, 6.78 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.384 g, 0.62 mmol), Palladium acetate (0.138 g, 0.62 mmol) and CESIUM CARBONATE (2.81 g, 8.62 mmol) added. The mixture was heated in the microwave ove... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | C1COCCN1.COC(=O)c1cc(Br)ccc1I>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].COCCOC>COC(=O)c1cc(Br)ccc1N1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-41816b2f53f7429c8faade84ae4a9bb3 | C1COCCN1.COC(=O)c1ccc(I)c(Br)c1>>COC(=O)c1ccc(N2CCOCC2)c(Br)c1 | COC(=O)C1=CC(=C(C=C1)I)Br.C1COCCN1>>COC(=O)C1=CC(=C(C=C1)N2CCOCC2)Br | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][c:15]1[Br:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[c:15]([Br:16])[cH:17]1 | C1COCCN1.COC(=O)c1ccc(I)c(Br)c1 | COC(=O)c1ccc(N2CCOCC2)c(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] | COCCOC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Br;D1;H0:5]):[c:6].[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[Br;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 32.45 | [{"value": 32.45, "product": "COC(=O)C1=CC(=C(C=C1)N2CCOCC2)Br", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To a solution of methyl 3-bromo-4-iodobenzoate (1.981 g, 5.81 mmol) in DME (10 mL) were morpholine (0.559 mL, 6.39 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.362 g, 0.58 mmol), Palladium acetate (0.130 g, 0.58 mmol) and CESIUM CARBONATE (3.79 g, 11.62 mmol) added. The mixture was heated in the microwave ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].COCCOC | 110 | null | C1COCCN1.COC(=O)c1ccc(I)c(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].COCCOC>COC(=O)c1ccc(N2CCOCC2)c(Br)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b29ef8d1a159427bbf8a6af5f4e4397e | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1>>CN(C)C(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC(=C1)Br)F.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:14]1[cH:15][cH:16][cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][C... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1 | CN(C)C(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 41.12 | [{"value": 41.12, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.93 mg, 0.02 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (130 mg, 0.35 mmol), 1-bromo-3-fluorobenzene (0.049 ml, 0.44 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.25 mg, 0.03 mmol) and cesium carbonate... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2b09b0edd9af4f8e80b89621d51beb35 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1ccc(=O)n(C)c1>>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1ccc(=O)n(C)c1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CN1C=C(C=CC1=O)C2=C(N=C(C=C2)N)OC>>CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(C(=O)C=C4)C)OC)C5=CC=CC=C5 | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[c:28]1[cH:29][cH:30][c:31](=[O:32])[n:33]([CH3:34])[cH:35]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:1... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1ccc(=O)n(C)c1 | COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1ccc(=O)n(C)c1 | CCC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1ccc(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CNC4)nc2)c[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 35.11 | [{"value": 35.11, "product": "CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(C(=O)C=C4)C)OC)C5=CC=CC=C5", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (300 mg, 1.09 mmol), 5-(6-amino-2-methoxypyridin-3-yl)-1-methylpyridin-2(1H)-one (253 mg, 1.09 mmol), Palladium(II) acetate (24.51 mg, 0.11 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (63.2 mg, 0.11 mmol) and Sodium tert-pentoxide (... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccncc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1ccncc1 | HCl | CCC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1ccc(=O)n(C)c1>CCC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1ccc(=O)n(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-18a40927a9754d74b579f5f2e9251be2 | CN(C)CCOc1ccc(N)nc1.Cc1c(Cl)ncnc1-n1cnc2ccccc21>>Cc1c(Nc2ccc(OCCN(C)C)cn2)ncnc1-n1cnc2ccccc21 | CC1=C(N=CN=C1Cl)N2C=NC3=CC=CC=C32.CN(C)CCOC1=CN=C(C=C1)N>>CC1=C(N=CN=C1N2C=NC3=CC=CC=C32)NC4=NC=C(C=C4)OCCN(C)C | [NH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]([CH3:13])[CH3:14])[cH:15][n:16]1.Cl[c:3]1[c:2]([CH3:1])[c:20](-[n:21]2[cH:22][n:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[n:19][cH:18][n:17]1>>[CH3:1][c:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]([CH3:13])[CH3:14])[cH:15][n:16]2)[n... | CN(C)CCOc1ccc(N)nc1.Cc1c(Cl)ncnc1-n1cnc2ccccc21 | Cc1c(Nc2ccc(OCCN(C)C)cn2)ncnc1-n1cnc2ccccc21 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(-n3cnc4ccccc43)ncn2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7;a:6]):[c:7]:1-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[#7;a:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]):[c:7]:1-[C;D1;H3:8] | 17.82 | [{"value": 17.82, "product": "CC1=C(N=CN=C1N2C=NC3=CC=CC=C32)NC4=NC=C(C=C4)OCCN(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (44.2 mg, 0.05 mmol) was added to 5-(2-(dimethylamino)ethoxy)pyridin-2-amine (175 mg, 0.97 mmol), 1-(6-chloro-5-methylpyrimidin-4-yl)-1H-benzo[d]imidazole (236 mg, 0.97 mmol), sodium t-butoxide (139 mg, 1.45 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (84... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1.c1ccc2[nH]cnc2c1 | HCl | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CN(C)CCOc1ccc(N)nc1.Cc1c(Cl)ncnc1-n1cnc2ccccc21>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>Cc1c(Nc2ccc(OCCN(C)C)cn2)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-41f70b81482a4604b6fa5a5e06a3c5e0 | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH2:20][N:21]([CH3:22])[CH2:23]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:24][cH:25][c:26]1-[c:27]1[cH:28][n:29][n:30]([CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]... | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OCCNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 49.97 | [{"value": 49.97, "product": "CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | A reaction mixture of 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.605 g, 2.16 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.440 g, 2.16 mmol), Cs2CO3 (1.053 g, 3.23 mmol), Tri-t-butylphosphonium tetrafluoroborate (0.063 g, 0.22 mmol) and Bis(dibenzyliden... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].COCCOC | 120 | null | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2bf6474a05bf4e7793ad68ef44642c0b | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH2:20][N:21]([CH3:22])[CH2:23]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:24][cH:25][c:26]1-[c:27]1[cH:28][n:29][n:30]([CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]... | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OCCNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 85.35 | [{"value": 85.35, "product": "CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A reaction mixture of 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.044 g, 0.09 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.019 g, 0.09 mmol), Cs2CO3 (0.046 g, 0.14 mmol), Tri-t-butylphosphonium tetrafluoroborate (2.73 mg, 9.41 µmol) and Bis(dibenzyliden... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f5f1be85a079463c9088e7a774cb07f5 | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH2:20][N:21]([CH3:22])[CH2:23]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:24][cH:25][c:26]1-[c:27]1[cH:28][n:29][n:30]([CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]... | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OCCNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 33.89 | [{"value": 33.89, "product": "CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (60 % purity, 314 mg, 0.67 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (137 mg, 0.67 mmol), PALLADIUM(II) ACETATE (15.07 mg, 0.07 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (23.53 mg, 0.07 mmol) and Cs2CO3 (328 mg, 1... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1b74a22b0fac45709f44bd49ada94b7f | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH2:20][N:21]([CH3:22])[CH2:23]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:24][cH:25][c:26]1-[c:27]1[cH:28][n:29][n:30]([CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]... | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OCCNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 36.71 | [{"value": 36.71, "product": "CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A reaction mixture of 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.341 g, 1.21 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.248 g, 1.21 mmol), PALLADIUM(II) ACETATE (0.027 g, 0.12 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (0.043 g, 0.12 mmol) and Cs2CO3 (... | 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.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-127ed8ac0e574ba4a6f68accaf8c96d2 | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2Oc3nc(Cl)ccc3CN(C)C2C)n1>>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)C(C)N(C)C3)ccc1-c1cnn(C)c1 | CC1C(OC2=C(CN1C)C=CC(=N2)Cl)C3=NC(=CS3)C.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1C(OC2=C(CN1C)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=NC(=CS5)C | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:26][cH:27][c:28]1-[c:29]1[cH:30][n:31][n:32]([CH3:33])[cH:34]1.Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[n:16][c:17]([CH3:18])[cH:19][s:20]1)[CH:21]([CH3:22])[N:23]([CH3:24])[CH2:25]2>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12... | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2Oc3nc(Cl)ccc3CN(C)C2C)n1 | COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)C(C)N(C)C3)ccc1-c1cnn(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1csc(C2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)cn4)nc3O2)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 73.35 | [{"value": 73.35, "product": "CC1C(OC2=C(CN1C)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=NC(=CS5)C", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.086 g, 0.42 mmol) in DME (3 mL) were 8-chloro-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.130 g, 0.42 mmol), cesium carbonate (0.205 g, 0.63 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.015 g, 0.04 mmol) and Palladium ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccncc1.c1cnc2c(c1)C[NH]CCO2.c1cscn1.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 110 | null | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2Oc3nc(Cl)ccc3CN(C)C2C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)C(C)N(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f5b45295d816488bbc3b0ba43fcc57fb | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC(=C1)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:20]2[o:21][c:22]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[cH:29][c:30](=[O:31])[c:32]2[cH:33]1.Br[c:13]1[cH:14][cH:15][cH:16][c:17]([F:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][N:12]... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 78.55 | [{"value": 78.55, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.33 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (121 mg, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (16.61 mg, 0.03 mmol), 1-bromo-3-fluorobenzene (0.047 ml, 0.42 mmol) and cesium carbonate (165 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bb0e774de3f94be78f90a0c79c7e9a7e | C1COCCN1.COC(=O)c1cc(Br)c(OC)cc1Cl>>COC(=O)c1cc(N2CCOCC2)c(OC)cc1Cl | COC1=C(C=C(C(=C1)Cl)C(=O)OC)Br.C1COCCN1>>COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2 | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:18]([Cl:19])[cH:17][c:14]1[O:15][CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([O:15][CH3:16])[cH:17][c:18]1[Cl:19] | C1COCCN1.COC(=O)c1cc(Br)c(OC)cc1Cl | COC(=O)c1cc(N2CCOCC2)c(OC)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 | 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](-[#8:8]):[c:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#8:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[#8:10]-[C:11]-[C:12]-1):[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6] | 79.91 | [{"value": 79.91, "product": "COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (0.040 g, 0.18 mmol), methyl 2-chloro-4-methoxy-5-morpholinobenzoate (2.042 g, 80 %), cesium carbonate (4.08 g, 12.52 mmol) and racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.223 g, 0.36 mmol) were mixed together in a round bottom flask and evacuated then purged with nitrogen. Morpholine ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | C1COCCN1.COC(=O)c1cc(Br)c(OC)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>COC(=O)c1cc(N2CCOCC2)c(OC)cc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ae9e42c4adac4ee7b754752b65453944 | C1COCCN1.COC(=O)c1cc(Br)c(OC)cc1Cl>>COC(=O)c1cc(N2CCOCC2)c(OC)cc1Cl | COC1=C(C=C(C(=C1)Cl)C(=O)OC)Br.C1COCCN1>>COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2 | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:18]([Cl:19])[cH:17][c:14]1[O:15][CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([O:15][CH3:16])[cH:17][c:18]1[Cl:19] | C1COCCN1.COC(=O)c1cc(Br)c(OC)cc1Cl | COC(=O)c1cc(N2CCOCC2)c(OC)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 | 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](-[#8:8]):[c:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#8:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[#8:10]-[C:11]-[C:12]-1):[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6] | 54.38 | [{"value": 54.38, "product": "COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Methyl 5-bromo-2-chloro-4-methoxybenzoate (1.486 g, 5.32 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.132 g, 0.21 mmol), palladium(II) acetate (0.024 g, 0.11 mmol) and cesium carbonate (2.425 g, 7.44 mmol) were mixed together and evacuated then purged with nitrogen. Toluene (10 mL) and morpholine (0.464 mL, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | C1COCCN1.COC(=O)c1cc(Br)c(OC)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>COC(=O)c1cc(N2CCOCC2)c(OC)cc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2610125450c14ea7bf8065e49fb7bdae | C1COCCN1.COC(=O)c1cc(Br)c(OC)cc1Cl>>COC(=O)c1cc(N2CCOCC2)c(OC)cc1Cl | COC1=C(C=C(C(=C1)Cl)C(=O)OC)Br.C1COCCN1>>COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2 | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:18]([Cl:19])[cH:17][c:14]1[O:15][CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([O:15][CH3:16])[cH:17][c:18]1[Cl:19] | C1COCCN1.COC(=O)c1cc(Br)c(OC)cc1Cl | COC(=O)c1cc(N2CCOCC2)c(OC)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 | 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](-[#8:8]):[c:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#8:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[#8:10]-[C:11]-[C:12]-1):[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6] | 78.74 | [{"value": 78.74, "product": "COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Cesium carbonate (3.78 g, 11.61 mmol), methyl 5-bromo-2-chloro-4-methoxybenzoate (2.317 g, 8.29 mmol), palladium(II) acetate (0.037 g, 0.17 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.206 g, 0.33 mmol) were combined and evacuated and purged with nitrogen (3 times). Degassed toluene (30 mL) and morpholine... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | C1COCCN1.COC(=O)c1cc(Br)c(OC)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>COC(=O)c1cc(N2CCOCC2)c(OC)cc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-75e934c9ac8c4736a342c35dfcb5f15c | COc1ccc([N+](=O)[O-])cc1Br.Nc1ncc(Cl)c(-c2cnn3ccccc23)n1>>COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2cnn3ccccc23)n1 | COC1=C(C=C(C=C1)[N+](=O)[O-])Br.C1=CC2=C(C=NN2C=C1)C3=NC(=NC=C3Cl)N>>COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=C4C=CC=CN4N=C3)Cl | Br[c:11]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10]1.[NH2:12][c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18](-[c:19]2[cH:20][n:21][n:22]3[cH:23][cH:24][cH:25][cH:26][c:27]23)[n:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[NH:12][c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18](... | COc1ccc([N+](=O)[O-])cc1Br.Nc1ncc(Cl)c(-c2cnn3ccccc23)n1 | COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2cnn3ccccc23)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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3cnn4ccccc34)n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[#8:5]-[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] | 4 | [{"value": 4.0, "product": "COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=C4C=CC=CN4N=C3)Cl", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | _Crude SM used_ 2-bromo-1-methoxy-4-nitrobenzene (0.029 g, 0.13 mmol), 5-chloro-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (0.031 g, 0.125 mmol) and cesium carbonate (0.057 g, 0.18 mmol) were suspended in dry dioxane (2 mL) the mixture degassed with nitrogen for 10 minutes. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccn2nccc2c1 | 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 | 150 | null | COc1ccc([N+](=O)[O-])cc1Br.Nc1ncc(Cl)c(-c2cnn3ccccc23)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>COc1ccc([N+... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d45c4d4f76fd453681edb48cc851d97a | COc1ccc([N+](=O)[O-])cc1Br.Nc1ncc(Cl)c(-c2cnn3ccccc23)n1>>COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2cnn3ccccc23)n1 | COC1=C(C=C(C=C1)[N+](=O)[O-])Br.C1=CC2=C(C=NN2C=C1)C3=NC(=NC=C3Cl)N>>COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=C4C=CC=CN4N=C3)Cl | Br[c:11]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10]1.[NH2:12][c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18](-[c:19]2[cH:20][n:21][n:22]3[cH:23][cH:24][cH:25][cH:26][c:27]23)[n:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[NH:12][c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18](... | COc1ccc([N+](=O)[O-])cc1Br.Nc1ncc(Cl)c(-c2cnn3ccccc23)n1 | COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2cnn3ccccc23)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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3cnn4ccccc34)n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[#8:5]-[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] | 4 | [{"value": 4.0, "product": "COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=C4C=CC=CN4N=C3)Cl", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | _Crude SM used_ 2-bromo-1-methoxy-4-nitrobenzene (0.029 g, 0.13 mmol), 5-chloro-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (0.031 g, 0.125 mmol) and cesium carbonate (0.057 g, 0.18 mmol) were suspended in dry dioxane (2 mL) the mixture degassed with nitrogen for 10 minutes. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccn2nccc2c1 | 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 | 150 | null | COc1ccc([N+](=O)[O-])cc1Br.Nc1ncc(Cl)c(-c2cnn3ccccc23)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>COc1ccc([N+... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-31e2f0a986f6432689bfa64e01da3c0f | CN(C)C(=O)Cc1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1>>CN(C)C(=O)Cc1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 | CN(C)C(=O)CC1=CC=C(C=C1)Br.C1C[C@@H](C2=NC(=NN2C1)N)C3=CC=C(C=C3)F>>CN(C)C(=O)CC1=CC=C(C=C1)NC2=NN3CCCC(C3=N2)C4=CC=C(C=C4)F | Br[c:10]1[cH:9][cH:8][c:7]([CH2:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:29][cH:28]1.[NH2:11][c:12]1[n:13][c:14]2[n:15]([n:16]1)[CH2:17][CH2:18][CH2:19][C@@H:20]2[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][c:14]3[n:15]([n:16]... | CN(C)C(=O)Cc1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1 | CN(C)C(=O)Cc1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc3n(n2)CCCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[NH2;D1;+0:10]):[#7;a:11]:[c:12]:1>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[#7;a:11]:[c:12]:1 | 32.03 | [{"value": 32.03, "product": "CN(C)C(=O)CC1=CC=C(C=C1)NC2=NN3CCCC(C3=N2)C4=CC=C(C=C4)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (94 mg, 0.40 mmol), 2-(4-bromophenyl)-N,N-dimethylacetamide (103 mg, 0.40 mmol), Cesium carbonate (198 mg, 0.61 mmol), Palladium(II) acetate (9.09 mg, 0.04 mmol) and 2-(Dicyclohexylphosphino)biphenyl (14.18 mg, 0.04 mmol) were added to a 0.5-2 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1nc2n(n1)CCCC2.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CN(C)C(=O)Cc1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)Cc1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bf7cf9ac04cd4fedb1f93e4a263e0d2f | CN1Cc2ccc(Cl)nc2OC(C2CC(F)(F)C2)C1.COc1nc(N)ccc1-c1cnn(C)c1>>COc1nc(Nc2ccc3c(n2)OC(C2CC(F)(F)C2)CN(C)C3)ccc1-c1cnn(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3CC(C3)(F)F.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5CC(C5)(F)F | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH:15]1[CH2:16][C:17]([F:18])([F:19])[CH2:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[c:28]1[cH:29][n:30][n:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O... | CN1Cc2ccc(Cl)nc2OC(C2CC(F)(F)C2)C1.COc1nc(N)ccc1-c1cnn(C)c1 | COc1nc(Nc2ccc3c(n2)OC(C2CC(F)(F)C2)CN(C)C3)ccc1-c1cnn(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.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OC(C2CCC2)CNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 69.57 | [{"value": 69.57, "product": "CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5CC(C5)(F)F", "details": "", "is_desired": true}] | 145 | CELSIUS | null | null | Palladium(II) acetate (0.019 g, 0.08 mmol) and 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.096 g, 0.17 mmol) were added to a degassed solution of 8-chloro-2-(3,3-difluorocyclobutyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.160 g, 0.55 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine ... | 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.C1CCC1.c1cn[nH]c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 145 | null | CN1Cc2ccc(Cl)nc2OC(C2CC(F)(F)C2)C1.COc1nc(N)ccc1-c1cnn(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.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1nc(Nc2ccc3c(n2)OC(C2CC(F)(F)C2)CN(C)C3)ccc1-c1cnn(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9455bd6f5eee4a2d8aef36cf7b2f19e8 | Clc1cccc(Cl)n1.N#Cc1ccc(Cl)cc1N>>N#Cc1ccc(Cl)cc1Nc1cccc(Cl)n1 | C1=CC(=NC(=C1)Cl)Cl.C1=CC(=C(C=C1Cl)N)C#N>>C1=CC(=NC(=C1)Cl)NC2=C(C=CC(=C2)Cl)C#N | Cl[c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[n:17]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[NH2:10]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[n:17]1 | Clc1cccc(Cl)n1.N#Cc1ccc(Cl)cc1N | N#Cc1ccc(Cl)cc1Nc1cccc(Cl)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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | 93.49 | [{"value": 93.49, "product": "C1=CC(=NC(=C1)Cl)NC2=C(C=CC(=C2)Cl)C#N", "details": "", "is_desired": true}] | 112 | CELSIUS | null | null | A mixture of 2,6-dichloropyridine (2 g, 13.51 mmol), 2-amino-4-chlorobenzonitrile (2.062 g, 13.51 mmol), PALLADIUM(II) ACETATE (0.303 g, 1.35 mmol), BINAP (1.683 g, 2.70 mmol) and potassium carbonate (5.60 g, 40.54 mmol) in toluene (100 mL) was stirred at reflux under N2 for 5hrs. LCMS detected major peak as desire pro... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | 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 | 112 | null | Clc1cccc(Cl)n1.N#Cc1ccc(Cl)cc1N>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>N#Cc1ccc(Cl)cc1Nc1cccc(Cl)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1d8bd79c0b354417a5f4e9ed2f70cdf8 | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N>>COc1c(Nc2ccc(S(C)(=O)=O)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 | CC(C)OC(=O)N1CCC(CC1)OC2=C(C(=NC=N2)Cl)OC.CC1=C(C=CC(=N1)S(=O)(=O)C)N>>CC1=C(C=CC(=N1)S(=O)(=O)C)NC2=C(C(=NC=N2)OC3CCN(CC3)C(=O)OC(C)C)OC | Cl[c:4]1[c:3]([O:2][CH3:1])[c:20]([O:21][CH:22]2[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][CH:29]([CH3:30])[CH3:31])[CH2:32][CH2:33]2)[n:19][cH:18][n:17]1.[NH2:5][c:6]1[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[n:14][c:15]1[CH3:16]>>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:1... | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N | COc1c(Nc2ccc(S(C)(=O)=O)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2cc(OC3CCNCC3)ncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[#8:8].[C;D1;H3:9]-[c:10](:[#7;a:11]:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:13](:[c:15]):[c:10](-[C;D1;H3:9]):[#7;a:11]:[c:12]):[c:7]:1-[#8:8] | 78.45 | [{"value": 78.45, "product": "CC1=C(C=CC(=N1)S(=O)(=O)C)NC2=C(C(=NC=N2)OC3CCN(CC3)C(=O)OC(C)C)OC", "details": "", "is_desired": true}] | 60 | CELSIUS | null | null | Bis[(2-diphenylphosphino)phenyl] ether (0.274 g, 0.51 mmol) was added in one portion to Palladium(II) acetate (0.057 g, 0.25 mmol) in toluene (5 mL) (degassed by bubbling N2 through it for 30 minutes) at 20°C under nitrogen (this mixture was also degassed by vacuum / N2 six times). After a few minutes a yellow suspensi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1.C1CC[NH]CC1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 60 | null | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1c(Nc2ccc(S(C)(=O)=O)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-69afe546f2d1404c8a01676e785a3836 | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N>>COc1c(Nc2ccc(S(C)(=O)=O)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 | CC(C)OC(=O)N1CCC(CC1)OC2=C(C(=NC=N2)Cl)OC.CC1=C(C=CC(=N1)S(=O)(=O)C)N>>CC1=C(C=CC(=N1)S(=O)(=O)C)NC2=C(C(=NC=N2)OC3CCN(CC3)C(=O)OC(C)C)OC | Cl[c:4]1[c:3]([O:2][CH3:1])[c:20]([O:21][CH:22]2[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][CH:29]([CH3:30])[CH3:31])[CH2:32][CH2:33]2)[n:19][cH:18][n:17]1.[NH2:5][c:6]1[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[n:14][c:15]1[CH3:16]>>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:1... | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N | COc1c(Nc2ccc(S(C)(=O)=O)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2cc(OC3CCNCC3)ncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[#8:8].[C;D1;H3:9]-[c:10](:[#7;a:11]:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:13](:[c:15]):[c:10](-[C;D1;H3:9]):[#7;a:11]:[c:12]):[c:7]:1-[#8:8] | 49.95 | [{"value": 49.95, "product": "CC1=C(C=CC(=N1)S(=O)(=O)C)NC2=C(C(=NC=N2)OC3CCN(CC3)C(=O)OC(C)C)OC", "details": "", "is_desired": true}] | 60 | CELSIUS | null | null | Bis[(2-diphenylphosphino)phenyl] ether (0.021 g, 0.04 mmol) was added in one portion to Palladium(II) acetate (4.33 mg, 0.02 mmol) in toluene (1 mL) (degassed by bubbling N2 through it for 30 minutes) at 20°C under nitrogen. After a few minutes a yellow suspension had formed. This added in one portion by pipette to a m... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1.C1CC[NH]CC1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 60 | null | COc1c(Cl)ncnc1OC1CCN(C(=O)OC(C)C)CC1.Cc1nc(S(C)(=O)=O)ccc1N>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1c(Nc2ccc(S(C)(=O)=O)nc2C)ncnc1OC1CCN(C(=O)OC(C)C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-db5f6efbde1f4ab4bc3688dd8d2a4d0e | Clc1ccnc(Cl)c1.NCc1ccccc1>>Clc1ccnc(NCc2ccccc2)c1 | C1=CN=C(C=C1Cl)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=NC=CC(=C2)Cl | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:15]1.[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1 | Clc1ccnc(Cl)c1.NCc1ccccc1 | Clc1ccnc(NCc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8]):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1=CC=C(C=C1)CNC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | palladium(II) acetate (0.018 g, 0.08 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (0.066 g, 0.12 mmol), sodium tert-butoxide (0.194 g, 2.02 mmol), phenylmethanamine (0.110 mL, 1.01 mmol) and 2,4-dichloropyridine (0.151 mL, 1.01 mmol) were suspended in DME (4 mL) and sealed into a m... | 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+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC | 80 | null | Clc1ccnc(Cl)c1.NCc1ccccc1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>Clc1ccnc(NCc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c8c1812487cb45a2983e445d322bb930 | Clc1ccnc(Cl)c1.NCc1ccccc1>>Clc1ccnc(NCc2ccccc2)c1 | C1=CN=C(C=C1Cl)Cl.C1=CC=C(C=C1)CN>>C1=CC=C(C=C1)CNC2=NC=CC(=C2)Cl | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:15]1.[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1 | Clc1ccnc(Cl)c1.NCc1ccccc1 | Clc1ccnc(NCc2ccccc2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8]):[#7;a:2]:[c:3] | 0 | [{"value": 0.0, "product": "C1=CC=C(C=C1)CNC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | phenylmethanamine (0.111 mL, 1.01 mmol), 2,4-dichloropyridine (0.151 mL, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in 1,4-dioxane (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Clc1ccnc(Cl)c1.NCc1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Clc1ccnc(NCc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ad988bfa2c604ea4b0ba123e57d761fa | CC(C)CN.Clc1ccnc(Cl)c1>>CC(C)CNc1cc(Cl)ccn1 | C1=CN=C(C=C1Cl)Cl.CC(C)CN>>CC(C)CNC1=NC=CC(=C1)Cl | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].Cl[c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][n:12]1 | CC(C)CN.Clc1ccnc(Cl)c1 | CC(C)CNc1cc(Cl)ccn1 | 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 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a: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](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CC(C)CNC1=NC=CC(=C1)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | palladium(II) acetate (0.018 g, 0.08 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (0.066 g, 0.12 mmol), sodium tert-butoxide (0.194 g, 2.02 mmol), 2-methylpropan-1-amine (0.100 mL, 1.01 mmol) and 2,4-dichloropyridine (0.151 mL, 1.01 mmol) were suspended in DME (4 mL) and sealed in... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | 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].COCCOC | 80 | null | CC(C)CN.Clc1ccnc(Cl)c1>CC(C)(C)[O-].[Na+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].COCCOC>CC(C)CNc1cc(Cl)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0addbbece6dc4ca2acdd8d8c9131d423 | Brc1cccc(OCc2ccccc2)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1>>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | C1=CC=C(C=C1)COC2=CC(=CC=C2)Br.CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F>>CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F | Br[c:16]1[cH:17][cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1.[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[nH:15]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[n:15]1-[c:16]1[cH:17][cH:... | Brc1cccc(OCc2ccccc2)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1 | Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 182cca01a9f197030c47a75855a36f35525847b56135a2d8de329e1d393e880c | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(COc2cccc(-n3ccc4ccccc43)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 59.07 | [{"value": 59.07, "product": "CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | EN04773-53, _Buchwald coupling, toluene and bromide_ The indole from 4773-25, 1-(benzyloxy)-3-bromobenzene,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 100 °C for 2h. Ca 60% conversion according to LCMS (product at 2.31 min). This conversion rate seemed faster than for the corresp... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | Brc1cccc(OCc2ccccc2)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1>CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f89f3a46444e42c0973a5acc34e50e60 | Brc1cccc(OCc2ccccc2)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1>>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | C1=CC=C(C=C1)COC2=CC(=CC=C2)Br.CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F>>CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F | Br[c:16]1[cH:17][cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1.[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[nH:15]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[n:15]1-[c:16]1[cH:17][cH:... | Brc1cccc(OCc2ccccc2)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1 | Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 182cca01a9f197030c47a75855a36f35525847b56135a2d8de329e1d393e880c | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(COc2cccc(-n3ccc4ccccc43)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 62.48 | [{"value": 62.48, "product": "CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | EN04773-54, _Buchwald coupling, toluene and bromide_ The indole from 4773-41, 1-(benzyloxy)-3-bromobenzene,Pd2(dba)3 (5mol%), JohnPhos (10mol%) and KOtBu (1.4eq) were dissolved in toluene. The mixture was warmed at 80 °C for 40 hours.* The reaction was carefully monitored and analysis data from 2h, 4, 16 and 40 h are ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 80 | null | Brc1cccc(OCc2ccccc2)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1>CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-23a7de6b0dd840ca8622691442279b4f | C1CNC1.N#Cc1ccc(Br)cc1>>N#Cc1ccc(N2CCC2)cc1 | C1=CC(=CC=C1C#N)Br.C1CNC1>>C1CN(C1)C2=CC=C(C=C2)C#N | [NH:7]1[CH2:8][CH2:9][CH2:10]1.Br[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:12][cH:11]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10]2)[cH:11][cH:12]1 | C1CNC1.N#Cc1ccc(Br)cc1 | N#Cc1ccc(N2CCC2)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 | acd899655e2b0e86ceef4a9d181b61426359f3e69c77ab85f60116fcc1919812 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 61.99 | [{"value": 61.99, "product": "C1CN(C1)C2=CC=C(C=C2)C#N", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 4-bromobenzonitrile (1.355 g, 7.44 mmol) and Sodium tert-butoxide (1.073 g, 11.17 mmol) were mixed in toluene (10 mL) and degassed by passing nitrogen for 5 min. Then Azetidine (1 mL, 14.89 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.172 g, 0.30 mmol) and Palladium(II) acetate (0.050 g, 0.22 mmol)were add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNC1.c1ccccc1 | c1ccccc1.C1C[NH]C1 | c1ccccc1.C1C[NH]C1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | C1CNC1.N#Cc1ccc(Br)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>N#Cc1ccc(N2CCC2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-316cf52c137541f4a2a9960bf7cb84d3 | CC(C)(C)OC(=O)N1CCNCC1.Cc1ncccc1Br>>Cc1ncccc1N1CCN(C(=O)OC(C)(C)C)CC1 | CC1=C(C=CC=N1)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC1=C(C=CC=N1)N2CCN(CC2)C(=O)OC(C)(C)C | [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[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[N: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 | CC(C)(C)OC(=O)N1CCNCC1.Cc1ncccc1Br | Cc1ncccc1N1CCN(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 | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1 | 92.54 | [{"value": 92.54, "product": "CC1=C(C=CC=N1)N2CCN(CC2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium acetate (65 mg, 0.29 mmol) and RuPhos (271mg, 0.58mmol) were dissolved in toluene (10 mL), degassed and purged with nitrogen and warmed to 50°C for 15 minutes. In a separate vessel, were mixed 3-bromo-2-methyl pyridine (1.00g, 5.81 mmol), BOC-piperazine (1.08g, 5.81mmol), sodium tertbutoxide and toluene (17 ... | 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 | 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.Cc1ncccc1Br>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>Cc1ncccc1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4147e405915e4ea7b4607546c536b535 | CC(C)(C)OC(=O)N1CCNCC1.Cc1ncccc1Br>>Cc1ncccc1N1CCN(C(=O)OC(C)(C)C)CC1 | CC1=C(C=CC=N1)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC1=C(C=CC=N1)N2CCN(CC2)C(=O)OC(C)(C)C | [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[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[N: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 | CC(C)(C)OC(=O)N1CCNCC1.Cc1ncccc1Br | Cc1ncccc1N1CCN(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 | 49ecdc6f3d334c1a9ca52eb9c498cab83041068035897d5c0adfa24457cda3f6 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1 | 82.86 | [{"value": 82.86, "product": "CC1=C(C=CC=N1)N2CCN(CC2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | RuPhos (0.543 g, 1.16 mmol) and palladium (II) acetate (0.131 g, 0.58 mmol) were suspended in toluene (15 mL) at ambient temperature. The resulting mixture was degassed and purged several times and warmed to 50°C under nitrogen for 20 mins. In a separate vessel were mixed 3-bromo-2-methylpyridine (2 g, 11.63 mmol), te... | 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 | 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.Cc1ncccc1Br>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>Cc1ncccc1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5f9307492f2b4cadaa0478f3250edc2b | COc1cccc(Br)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1>>COc1cccc(-n2c(C)cc3ccc(OC(F)(F)F)cc32)c1 | COC1=CC(=CC=C1)Br.CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F>>CC1=CC2=C(N1C3=CC(=CC=C3)OC)C=C(C=C2)OC(F)(F)F | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23]1.[nH:8]1[c:9]([CH3:10])[cH:11][c:12]2[cH:13][cH:14][c:15]([O:16][C:17]([F:18])([F:19])[F:20])[cH:21][c:22]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[n:8]2[c:9]([CH3:10])[cH:11][c:12]3[cH:13][cH:14][c:15]([O:16][C:17]([F:18])([F:19])[F:20])[cH:21][c:22]23)[cH:23]... | COc1cccc(Br)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1 | COc1cccc(-n2c(C)cc3ccc(OC(F)(F)F)cc32)c1 | CC(C)(C)[O-].[Na+] | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 182cca01a9f197030c47a75855a36f35525847b56135a2d8de329e1d393e880c | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 65.49 | [{"value": 65.49, "product": "CC1=CC2=C(N1C3=CC(=CC=C3)OC)C=C(C=C2)OC(F)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | EN04773-51, _Buchwald coupling,_ ** _J. Med. Chem. 2009, page 3846-3854 (exactly same reaction)._** The indole from 4773-41, 1-bromo-3-methoxybenzenee,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 120 °C for 1h and ~65% conversion was observed on NMR*(see attached NMR). Reaction s... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2cc[nH]c2c1 | c1ccccc1.c1ccc2cc[nH]c2c1 | HBr | CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 120 | null | COc1cccc(Br)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1>CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1cccc(-n2c(C)cc3ccc(OC(F)(F)F)cc32)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-76b900b67381471d89fef9247f442cb0 | Brc1ccc(I)cc1.C[C@@H]1CNC[C@H](C)N1>>C[C@@H]1CN(c2ccc(Br)cc2)C[C@H](C)N1 | C1=CC(=CC=C1Br)I.C[C@@H]1CNC[C@@H](N1)C>>C[C@@H]1CN(C[C@@H](N1)C)C2=CC=C(C=C2)Br | I[c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:12][C@@H:13]([CH3:14])[NH:15]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[CH2:12][C@H:13]([CH3:14])[NH:15]1 | Brc1ccc(I)cc1.C[C@@H]1CNC[C@H](C)N1 | C[C@@H]1CN(c2ccc(Br)cc2)C[C@H](C)N1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d7148bc7995d5dfa1607e72989e75c64b789e6aafbd2cc3ab6637dcd843b0985 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | I-[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] | 61.61 | [{"value": 61.61, "product": "C[C@@H]1CN(C[C@@H](N1)C)C2=CC=C(C=C2)Br", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | sodium 2-methylpropan-2-olate (4.08 g, 42.42 mmol) was added to (2R,6S)-2,6-dimethylpiperazine (4.84 g, 42.42 mmol) in dioxane (300 mL) at 21°C under nitrogen. Stirred for 5 mins. 1-bromo-4-iodobenzene (8 g, 28.28 mmol) added, followed by diacetoxypalladium (0.635 g, 2.83 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCCN1 | C1CNCC[NH]1.c1ccccc1 | C1CNCC[NH]1.c1ccccc1 | 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].C1COCCO1 | 90 | null | Brc1ccc(I)cc1.C[C@@H]1CNC[C@H](C)N1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>C[C@@H]1CN(c2ccc(Br)cc2)C[C@H](C)N1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-609b92e7f381461a936ff9653aaca797 | Brc1ccc(I)cc1.C[C@@H]1CNC[C@H](C)N1>>C[C@@H]1CN(c2ccc(Br)cc2)C[C@H](C)N1 | C1=CC(=CC=C1Br)I.C[C@@H]1CNC[C@@H](N1)C>>C[C@@H]1CN(C[C@@H](N1)C)C2=CC=C(C=C2)Br | I[c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:12][C@@H:13]([CH3:14])[NH:15]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[CH2:12][C@H:13]([CH3:14])[NH:15]1 | Brc1ccc(I)cc1.C[C@@H]1CNC[C@H](C)N1 | C[C@@H]1CN(c2ccc(Br)cc2)C[C@H](C)N1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d7148bc7995d5dfa1607e72989e75c64b789e6aafbd2cc3ab6637dcd843b0985 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | I-[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] | 44.14 | [{"value": 44.14, "product": "C[C@@H]1CN(C[C@@H](N1)C)C2=CC=C(C=C2)Br", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | sodium 2-methylpropan-2-olate (0.510 g, 5.30 mmol) was added to (2R,6S)-2,6-dimethylpiperazine (0.605 g, 5.30 mmol) in dioxane (40 mL) at 21°C under nitrogen. Stirred for 5 mins. 1-bromo-4-iodobenzene (1 g, 3.53 mmol) added, followed by diacetoxypalladium (0.079 g, 0.35 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCCN1 | C1CNCC[NH]1.c1ccccc1 | C1CNCC[NH]1.c1ccccc1 | 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].C1COCCO1 | 90 | null | Brc1ccc(I)cc1.C[C@@H]1CNC[C@H](C)N1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>C[C@@H]1CN(c2ccc(Br)cc2)C[C@H](C)N1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c3293297b4c643b7b38f6be28fe8ecb0 | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cccc(F)c1-c1ccc(Br)cc1>>C[C@H](CNc1ccc(-c2c(F)cccc2F)cc1)O[Si](C)(C)C(C)(C)C | C1=CC(=C(C(=C1)F)C2=CC=C(C=C2)Br)F.C[C@H](CN)O[Si](C)(C)C(C)(C)C>>C[C@H](CNC1=CC=C(C=C1)C2=C(C=CC=C2F)F)O[Si](C)(C)C(C)(C)C | [CH3:1][C@H:2]([CH2:3][NH2:4])[O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26].Br[c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]2[F:16])[cH:17][cH:18]1>>[CH3:1][C@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]2[F:16])[cH:17][cH:18]1... | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cccc(F)c1-c1ccc(Br)cc1 | C[C@H](CNc1ccc(-c2c(F)cccc2F)cc1)O[Si](C)(C)C(C)(C)C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 59.39 | [{"value": 59.39, "product": "C[C@H](CNC1=CC=C(C=C1)C2=C(C=CC=C2F)F)O[Si](C)(C)C(C)(C)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | PdOAc2 (0.030 g, 0.13 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.064 g, 0.13 mmol) were added in one portion to a degassed solution of 4'-bromo-2,6-difluorobiphenyl (0.36 g, 1.34 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.355 g, 1.87 mmol) and cesium carbonate (0.654 g, 2.01... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cccc(F)c1-c1ccc(Br)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>C[C@H](CNc1ccc(-c2c(F)cccc2F)cc1)O[Si](C)(C)C(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9f41dcdcc0414ae7bc18304ff07e7d77 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 66.17 | [{"value": 66.17, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.020 g, 0.09 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (0.8g, 2.23 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.110 g, 0.19 mmol), 1-bromo-3,5-difluorobenzene (0.321 ml, 2.79 mmol) and cesium carbonate (1.0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-49d23b5c1f9b4ddcb11fd7200ac09018 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 71.91 | [{"value": 71.91, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.13 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (125 mg, 0.35 mmol), 1-bromo-3,5-difluorobenzene (0.044 ml, 0.38 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.15 mg, 0.03 mmol) and cesium carbonate (... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c8e3d8ddd10a4c0eb4a987f93f56cea7 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 67.33 | [{"value": 67.33, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.033 g, 0.15 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (1.326 g, 3.7 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.182 g, 0.31 mmol), 1-bromo-3,5-difluorobenzene (0.533 ml, 4.63 mmol) and cesium carbonate (1... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e061647f5f0c433f84efb82229734131 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 52.18 | [{"value": 52.18, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (6.26 mg, 0.03 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (200 mg, 0.56 mmol), 1-bromo-3,5-difluorobenzene (0.080 ml, 0.70 mmol) and cesium carbonate (273 mg, 0.84 mmol) dissolved in 1,4-dioxane (8 ml). The resulting suspension was ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e9a88816e360448bba740f2afb6125ad | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 65.89 | [{"value": 65.89, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (6.26 mg, 0.03 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (200 mg, 0.56 mmol), 1-bromo-3,5-difluorobenzene (0.080 ml, 0.70 mmol) and cesium carbonate (273 mg, 0.84 mmol) dissolved in 1,4-dioxane (8 ml). The resulting suspension was ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d28f2c89dd6e4f20843405febc9c45d8 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 67.04 | [{"value": 67.04, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.028 g, 0.13 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (0.9 g, 2.51 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.145 g, 0.25 mmol), 1-bromo-3,5-difluorobenzene (0.361 ml, 3.14 mmol) and cesium carbonate (1.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-14e85d02574d4d47b1620f5ef17dbbe5 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][c:15]([F:16])[cH:17][c:18]([F:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 56.04 | [{"value": 56.04, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.439 g, 1.95 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (14 g, 39.06 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.260 g, 3.91 mmol), 1-bromo-3,5-difluorobenzene (5.62 ml, 48.83 mmol) and cesium carbonate (19... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-232b7429c3f0450bb3d4836c8a002e13 | Cc1cc2ccc(OC(F)(F)F)cc2[nH]1.Ic1cccc(OCc2ccccc2)c1>>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | C1=CC=C(C=C1)COC2=CC(=CC=C2)I.CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F>>CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F | [CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[nH:15]1.I[c:16]1[cH:17][cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[n:15]1-[c:16]1[cH:17][cH:1... | Cc1cc2ccc(OC(F)(F)F)cc2[nH]1.Ic1cccc(OCc2ccccc2)c1 | Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)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 | OtherReaction | 182cca01a9f197030c47a75855a36f35525847b56135a2d8de329e1d393e880c | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(COc2cccc(-n3ccc4ccccc43)c2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 40.17 | [{"value": 40.17, "product": "CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | EN04773-50, _Buchwald coupling,_ ** _J. Med. Chem. 2009, page 3846-3854 (changed: solvent to dioxane and bromide to iodide)._** The indole from 4773-41, 1-(benzyloxy)-3-iodobenzene, Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 120 °C for 1h and ~40% conversion was observed on NMR... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1.c1ccccc1 | HI | CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)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 | 120 | null | Cc1cc2ccc(OC(F)(F)F)cc2[nH]1.Ic1cccc(OCc2ccccc2)c1>CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)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>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-055c0d9926684c29963cad751105f26e | Cc1cc2ccc(OC(F)(F)F)cc2[nH]1.Ic1cccc(OCc2ccccc2)c1>>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | C1=CC=C(C=C1)COC2=CC(=CC=C2)I.CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F>>CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F | [CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[nH:15]1.I[c:16]1[cH:17][cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[n:15]1-[c:16]1[cH:17][cH:1... | Cc1cc2ccc(OC(F)(F)F)cc2[nH]1.Ic1cccc(OCc2ccccc2)c1 | Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 | CC(C)(C)[O-].[Na+] | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 182cca01a9f197030c47a75855a36f35525847b56135a2d8de329e1d393e880c | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(COc2cccc(-n3ccc4ccccc43)c2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 10.45 | [{"value": 10.45, "product": "CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | EN04773-52, _Buchwald coupling, toluene and iodide_ The indole from 4773-25, 1-(benzyloxy)-3-iodobenzene,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 120 °C for 1h and 50% conversion was observed on NMR*(see attached NMR). The mixture was warmed further 15h at 120°C, still starti... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1.c1ccccc1 | HI | CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 120 | null | Cc1cc2ccc(OC(F)(F)F)cc2[nH]1.Ic1cccc(OCc2ccccc2)c1>CC(C)(C)[O-].[Na+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a21f7feeefae4ebba3375572e56f8ed0 | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cncc(Br)c1>>CC(C)(C)OC(=O)N1CC2CC1CN2c1cncc(C(F)(F)F)c1 | C1=C(C=NC=C1Br)C(F)(F)F.CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2>>CC(C)(C)OC(=O)N1CC2CC1CN2C3=CN=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][n: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][n:17][cH:18][c:19]([C:20]... | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cncc(Br)c1 | CC(C)(C)OC(=O)N1CC2CC1CN2c1cncc(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 | dfd0196214703888573680f39152bc1a6030b7a7909a66c487cf532b7436ad32 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CC3CC2CN3)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[C@@H;D3;+0:16]2-[C:17]-[C:18]-1-[C:19]-[NH;D2;+0:20]-2>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:13])-[#7:14]1-[C:15]-[CH;D3;+0:16]2-[C:17]-[... | 82.28 | [{"value": 82.28, "product": "CC(C)(C)OC(=O)N1CC2CC1CN2C3=CN=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 (225 mg, 0.36 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (138 mg, 0.15 mmol) dissolved in 1,4-dioxane (7.500 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 3-bromo-5-(trifluoromethyl)pyridine (340 mg, 1.50 mmol) f... | 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]C2C[NH]C1C2.c1ccncc1 | C1[NH]C2C[NH]C1C2.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].C1COCCO1 | 80 | null | CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2.FC(F)(F)c1cncc(Br)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC(C)(C)OC(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9b1d1f242a294d85b376889807570e77 | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cncc(Br)c1>>CC(C)(C)OC(=O)N1CCN(c2cncc(C(F)(F)F)c2)CC1 | C1=C(C=NC=C1Br)C(F)(F)F.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC(=C2)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.Br[c:12]1[cH:13][n:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH: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][n:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]2)[CH... | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cncc(Br)c1 | CC(C)(C)OC(=O)N1CCN(c2cncc(C(F)(F)F)c2)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] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c: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]:[#7;a:3]:[c:4]:[c:5]:[c:6]:2)-[C:11]-[C:12]-1 | 85.94 | [{"value": 85.94, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC(=C2)C(F)(F)F", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | A 100 ml round bottom equipped with stir bar was charged with (S)-BINAP (331 mg, 0.53 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (203 mg, 0.22 mmol) dissolved in 1,4-dioxane (10.700 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 3-bromo-5-(trifluoromethyl)pyridine (500 mg, 2.21 m... | 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 | 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)N1CCNCC1.FC(F)(F)c1cncc(Br)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC(C)(C)OC(=O)N1CCN(c2c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-45a7a9da12934ab5ab153542a819eb23 | CCNCC.N#Cc1ccc(Br)cc1>>CCN(CC)c1ccc(C#N)cc1 | C1=CC(=CC=C1C#N)Br.CCNCC>>CCN(CC)C1=CC=C(C=C1)C#N | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].Br[c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1 | CCNCC.N#Cc1ccc(Br)cc1 | CCN(CC)c1ccc(C#N)cc1 | C(=O)([O-])[O-].[K+].[K+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC#N | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C;D1;H3:10]>>[C;D1;H3:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C;D1;H3:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 39.17 | [{"value": 39.17, "product": "CCN(CC)C1=CC=C(C=C1)C#N", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | 4-Bromobenzonitrile (2.000 g, 10.99 mmol), diethylamine (3.41 mL, 32.96 mmol) and POTASSIUM CARBONATE (4.56 g, 32.96 mmol) were mixed in dry acetonitrile (10 mL) under argon in a microwave vial. The vial was sealed and heated with microvawes for 60 minutes at 160°C. Added diethylamine (3.41 mL, 32.96 mmol) and heated ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(=O)([O-])[O-].[K+].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC#N | 160 | null | CCNCC.N#Cc1ccc(Br)cc1>C(=O)([O-])[O-].[K+].[K+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC#N>CCN(CC)c1ccc(C#N)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-17225e99c02b4548adfeb78156e8b3d5 | Clc1cnccn1.Nc1cccc(S(N)(=O)=O)c1>>NS(=O)(=O)c1cccc(Nc2cnccn2)c1 | C1=CN=C(C=N1)Cl.C1=CC(=CC(=C1)S(=O)(=O)N)N>>C1=CC(=CC(=C1)S(=O)(=O)N)NC2=NC=CN=C2 | Cl[c:11]1[cH:12][n:13][cH:14][cH:15][n:16]1.[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:17]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][n:13][cH:14][cH:15][n:16]2)[cH:17]1 | Clc1cnccn1.Nc1cccc(S(N)(=O)=O)c1 | NS(=O)(=O)c1cccc(Nc2cnccn2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d8d76a4347a32a5acf79894f48887cf8d745ba4ca5f91e54084ebdbe25f43c75 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | 42.34 | [{"value": 42.34, "product": "C1=CC(=CC(=C1)S(=O)(=O)N)NC2=NC=CN=C2", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | A mixture of 3-aminobenzenesulfonamide (130mg, 0.75 mmol), 2-chloropyrazine (0.067 mL, 0.75 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (34.9 mg, 0.06 mmol), diacetoxypalladium (6.78 mg, 0.03 mmol) and cesium carbonate (295 mg, 0.91 mmol) in degassed DMA (2.1 mL) was heated **_in the microwave_** fo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 130 | null | Clc1cnccn1.Nc1cccc(S(N)(=O)=O)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>NS(=O)(=O)c1cccc(Nc2cnccn2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f980d50ac3ae43a58ddfe2efc500c048 | Brc1cncnc1.Nc1cccc(S(N)(=O)=O)c1>>NS(=O)(=O)c1cccc(Nc2cncnc2)c1 | C1=C(C=NC=N1)Br.C1=CC(=CC(=C1)S(=O)(=O)N)N>>C1=CC(=CC(=C1)S(=O)(=O)N)NC2=CN=CN=C2 | Br[c:11]1[cH:12][n:13][cH:14][n:15][cH:16]1.[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:17]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][n:13][cH:14][n:15][cH:16]2)[cH:17]1 | Brc1cncnc1.Nc1cccc(S(N)(=O)=O)c1 | NS(=O)(=O)c1cccc(Nc2cncnc2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cncnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | 18.77 | [{"value": 18.77, "product": "C1=CC(=CC(=C1)S(=O)(=O)N)NC2=CN=CN=C2", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | A mixture of 3-aminobenzenesulfonamide (110mg, 0.64 mmol), 5-bromopyrimidine (102 mg, 0.64 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.6 mg, 0.05 mmol), diacetoxypalladium (5.74 mg, 0.03 mmol) and cesium carbonate (250 mg, 0.77 mmol) in degassed DMA (1.9 mL) was heated **_in the microwave_** for... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 130 | null | Brc1cncnc1.Nc1cccc(S(N)(=O)=O)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>NS(=O)(=O)c1cccc(Nc2cncnc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8b74efad6e6646bdaf4fdb6de38026cc | N#CCc1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1>>N#CCc1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 | C1=CC(=CC=C1CC#N)Br.C1C[C@@H](C2=NC(=NN2C1)N)C3=CC=C(C=C3)F>>C1CC(C2=NC(=NN2C1)NC3=CC=C(C=C3)CC#N)C4=CC=C(C=C4)F | Br[c:7]1[cH:6][cH:5][c:4]([CH2:3][C:2]#[N:1])[cH:26][cH:25]1.[NH2:8][c:9]1[n:10][c:11]2[n:12]([n:13]1)[CH2:14][CH2:15][CH2:16][C@@H:17]2[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]3[n:12]([n:13]2)[CH2:14][CH2:15][CH2:16][CH:17]3[c:18]2[cH:19][cH:... | N#CCc1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1 | N#CCc1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4 | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc3n(n2)CCCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[NH2;D1;+0:10]):[#7;a:11]:[c:12]:1>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[#7;a:11]:[c:12]:1 | 42.09 | [{"value": 42.09, "product": "C1CC(C2=NC(=NN2C1)NC3=CC=C(C=C3)CC#N)C4=CC=C(C=C4)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (98 mg, 0.42 mmol), 2-(4-bromophenyl)acetonitrile (83 mg, 0.42 mmol), Cesium carbonate (206 mg, 0.63 mmol), Palladium(II) acetate (9.47 mg, 0.04 mmol) and 2-(Dicyclohexylphosphino)biphenyl (14.79 mg, 0.04 mmol) were added to a 2-5 mL microwave ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1nc2n(n1)CCCC2.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1COCCO1 | 120 | null | N#CCc1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1COCCO1>N#CCc1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2784ae4fbb2641c38c53b79f14f3e80f | CN1CCC[C@@H]1COc1ccc(N)nc1.Clc1cc(-n2cnc3ccccc32)ncn1>>CN1CCC[C@@H]1COc1ccc(Nc2cc(-n3cnc4ccccc43)ncn2)nc1 | C1=CC=C2C(=C1)N=CN2C3=CC(=NC=N3)Cl.CN1CCC[C@@H]1COC2=CN=C(C=C2)N>>CN1CCC[C@@H]1COC2=CN=C(C=C2)NC3=CC(=NC=N3)N4C=NC5=CC=CC=C54 | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]1[CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[n:29][cH:30]1.Cl[c:14]1[cH:15][c:16](-[n:17]2[cH:18][n:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]23)[n:26][cH:27][n:28]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]1[CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH:13][c:14]2[cH:15][... | CN1CCC[C@@H]1COc1ccc(N)nc1.Clc1cc(-n2cnc3ccccc32)ncn1 | CN1CCC[C@@H]1COc1ccc(Nc2cc(-n3cnc4ccccc43)ncn2)nc1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(c1)ncn2-c1cc(Nc2ccc(OC[C@H]3CCCN3)cn2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7;a:6]):[c:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[#7;a:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:7]:1 | 14.09 | [{"value": 14.09, "product": "CN1CCC[C@@H]1COC2=CN=C(C=C2)NC3=CC(=NC=N3)N4C=NC5=CC=CC=C54", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (31.6 mg, 0.03 mmol) was added to (R)-5-((1-methylpyrrolidin-2-yl)methoxy)pyridin-2-amine (143 mg, 0.69 mmol), 1-(6-chloropyrimidin-4-yl)-1H-benzo[d]imidazole (159 mg, 0.69 mmol), sodium t-butoxide (99 mg, 1.03 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CC[NH]C1.c1ccncc1.c1cncnc1.c1ccc2[nH]cnc2c1 | HCl | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CN1CCC[C@@H]1COc1ccc(N)nc1.Clc1cc(-n2cnc3ccccc32)ncn1>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>CN1CCC[C@@H]1COc1cc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7ce32a5d4abb4826b07e10a8720e8cf8 | C1CC2(CCN1)OCCO2.COc1cncc(Br)c1>>COc1cncc(N2CCC3(CC2)OCCO3)c1 | COC1=CC(=CN=C1)Br.C1CNCCC12OCCO2>>COC1=CN=CC(=C1)N2CCC3(CC2)OCCO3 | [NH:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[O:14][CH2:15][CH2:16][O:17]2.Br[c:7]1[cH:6][n:5][cH:4][c:3]([O:2][CH3:1])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][C:11]3([CH2:12][CH2:13]2)[O:14][CH2:15][CH2:16][O:17]3)[cH:18]1 | C1CC2(CCN1)OCCO2.COc1cncc(Br)c1 | COc1cncc(N2CCC3(CC2)OCCO3)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] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 98501ed119dbc1fd4801d293f69e3d6501dd1371a251bfd1836b1cb54df9f3d3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCC3(CC2)OCCO3)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1)-[C:10]-[C:11] | 75.12 | [{"value": 75.12, "product": "COC1=CN=CC(=C1)N2CCC3(CC2)OCCO3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 11/05 2011 07:58:54 +0200 A mixture of 3-bromo-5-methoxypyridine (1.5 g, 7.98 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (1.023 ml, 7.98 mmol), palladium(II) acetate (0.107 g, 0.48 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.228 g, 0.48 mmol) in toluene (38.3 ml) and tBuOH (7.65 ml) was evacuat... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CC2(CCN1)OCCO2.c1ccncc1 | c1ccncc1.C1CC2(CC[NH]1)OCCO2 | c1ccncc1.C1CC2(CC[NH]1)OCCO2 | 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 | 100 | null | C1CC2(CCN1)OCCO2.COc1cncc(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].CC1=CC=CC=C1>COc1cncc(N2CCC3(CC2)OCCO3)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-acf9860e722c4b4598d1b2c19d9e27a1 | Brc1cccnc1.Nc1cccnc1>>c1cncc(Nc2cccnc2)c1 | C1=CC(=CN=C1)Br.C1=CC(=CN=C1)N>>C1=CC(=CN=C1)NC2=CN=CC=C2 | Br[c:5]1[cH:4][n:3][cH:2][cH:1][cH:13]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[cH:1]1[cH:2][n:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[cH:13]1 | Brc1cccnc1.Nc1cccnc1 | c1cncc(Nc2cccnc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2cccnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[c:12]:[#7;a:11]:[c:10]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:9] | 9.97 | [{"value": 9.97, "product": "C1=CC(=CN=C1)NC2=CN=CC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Stock solution: 2.43 M solution of CyPF-tBu/Pd(OAc)2 (1:1) in DME. pyridin-3-amine (3.57 g, 37.98 mmol) was dissolved in DME (10 mL). To the mixture was added 10 mL of stock solution, and sodium tert-butoxide (4.26 g, 44.30 mmol). 5 min later, to the mixtue was added a solution of 3-bromopyridine (3.05 mL, 31.65 mmol)... | 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 | 100 | null | Brc1cccnc1.Nc1cccnc1>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>c1cncc(Nc2cccnc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8d4927e597524dbea6e64f777b1f4296 | Brc1cccnc1.Nc1cccnc1>>c1cncc(Nc2cccnc2)c1 | C1=CC(=CN=C1)Br.C1=CC(=CN=C1)N>>C1=CC(=CN=C1)NC2=CN=CC=C2 | Br[c:5]1[cH:4][n:3][cH:2][cH:1][cH:13]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[cH:1]1[cH:2][n:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[cH:13]1 | Brc1cccnc1.Nc1cccnc1 | c1cncc(Nc2cccnc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2cccnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[c:12]:[#7;a:11]:[c:10]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:9] | 3.62 | [{"value": 3.62, "product": "C1=CC(=CN=C1)NC2=CN=CC=C2", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Stock solution: 2.43 M solution of CyPF-tBu/Pd(OAc)2 (1:1) in DME. 3-bromopyridine (0.482 mL, 5.00 mmol) was dissolved in DME (10 mL). To the solution was added 2mL of stock solution, and sodium tert-butoxide (0.673 g, 7.00 mmol). To the mixture was added a solution of pyridin-3-amine (0.565 g, 6.00 mmol) in DME (10 m... | 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.Nc1cccnc1>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>c1cncc(Nc2cccnc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d32527b9fef34013a5ae697e40e160a3 | Brc1cccnc1.Nc1cccnc1>>c1cncc(Nc2cccnc2)c1 | C1=CC(=CN=C1)Br.C1=CC(=CN=C1)N>>C1=CC(=CN=C1)NC2=CN=CC=C2 | Br[c:5]1[cH:4][n:3][cH:2][cH:1][cH:13]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[cH:1]1[cH:2][n:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[cH:13]1 | Brc1cccnc1.Nc1cccnc1 | c1cncc(Nc2cccnc2)c1 | CC(C)(C)[O-].[Na+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2cccnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[c:12]:[#7;a:11]:[c:10]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:9] | 12.19 | [{"value": 12.19, "product": "C1=CC(=CN=C1)NC2=CN=CC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Stock solution: 2.43 M solution of CyPF-tBu/Pd(OAc)2 (1:1) in DME. 3-bromopyridine (6 mL, 62.28 mmol) was dissolved in DME (10 mL). To the solution was added 10 mL of stock solution, and sodium tert-butoxide (8.38 g, 87.19 mmol). To the mixture was added a solution of pyridin-3-amine (7.03 g, 74.74 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 | 100 | null | Brc1cccnc1.Nc1cccnc1>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>c1cncc(Nc2cccnc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-700c6d20880044119041252f015d9cec | CN(C)C(=O)c1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1>>CN(C)C(=O)c1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 | CN(C)C(=O)C1=CC=C(C=C1)Br.C1C[C@@H](C2=NC(=NN2C1)N)C3=CC=C(C=C3)F>>CN(C)C(=O)C1=CC=C(C=C1)NC2=NN3CCCC(C3=N2)C4=CC=C(C=C4)F | Br[c:9]1[cH:8][cH:7][c:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:28][cH:27]1.[NH2:10][c:11]1[n:12][c:13]2[n:14]([n:15]1)[CH2:16][CH2:17][CH2:18][C@@H:19]2[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]3[n:14]([n:15]2)[CH2:16][CH2:1... | CN(C)C(=O)c1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1 | CN(C)C(=O)c1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc3n(n2)CCCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[NH2;D1;+0:10]):[#7;a:11]:[c:12]:1>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[#7;a:11]:[c:12]:1 | 40.91 | [{"value": 40.91, "product": "CN(C)C(=O)C1=CC=C(C=C1)NC2=NN3CCCC(C3=N2)C4=CC=C(C=C4)F", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (101 mg, 0.43 mmol), 4-bromo-N,N-dimethylbenzamide (100 mg, 0.44 mmol), Cesium carbonate (211 mg, 0.65 mmol), Palladium(II) acetate (9.8 mg, 0.04 mmol) and 2-(Dicyclohexylphosphino)biphenyl (15.8 mg, 0.05 mmol) were added to a microwave vial. T... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1nc2n(n1)CCCC2.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CN(C)C(=O)c1ccc(Br)cc1.Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1ccc(Nc2nc3n(n2)CCCC3c2ccc(F)cc2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-16d84022ddba418d9531ecea75eeae83 | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.N#Cc1cc(F)cc(Br)c1>>CN(C)C(=O)c1cc(C2CCCN2c2cc(F)cc(C#N)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=C(C=C(C=C1F)Br)C#N.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)C#N)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:23]2[o:24][c:25]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[cH:32][c:33](=[O:34])[c:35]2[cH:36]1.Br[c:14]1[cH:15][c:16]([F:17])[cH:18][c:19]([C:20]#[N:21])[cH:22]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.N#Cc1cc(F)cc(Br)c1 | CN(C)C(=O)c1cc(C2CCCN2c2cc(F)cc(C#N)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 52.42 | [{"value": 52.42, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)C#N)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.93 mg, 0.02 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (130 mg, 0.35 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.25 mg, 0.03 mmol), 3-bromo-5-fluorobenzonitrile (88 mg, 0.44 mmol) and cesium carbona... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.N#Cc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2cc(F)cc(C#N)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2ff1a1a6512d42c193b559390cdb44ba | Brc1ccccc1.CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1>>CN(C)C(=O)c1cc(C2CCCN2c2ccccc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC=C(C=C1)Br.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=CC=C4)OC(=CC2=O)N5CCOCC5 | Br[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:20]2[o:21][c:22]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[cH:29][c:30](=[O:31])[c:32]2[cH:33]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][... | Brc1ccccc1.CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1 | CN(C)C(=O)c1cc(C2CCCN2c2ccccc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 37.67 | [{"value": 37.67, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=CC=C4)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.93 mg, 0.02 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (130 mg, 0.35 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.25 mg, 0.03 mmol), bromobenzene (0.046 ml, 0.44 mmol) and cesium carbonate (171 mg, 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Brc1ccccc1.CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2ccccc2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d0512d6367704fadb75940a278af6036 | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC=C1F)Br.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][C... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1 | CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 15 | [{"value": 15.0, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (7.56 mg, 0.03 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (250 mg, 0.67 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (38.9 mg, 0.07 mmol), 1-bromo-4-fluorobenzene (0.092 ml, 0.84 mmol) and cesium carbonate ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a63ed86656ab46e9b98fdae5bdec4fe4 | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC=C1F)Br.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][C... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1 | CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 19.15 | [{"value": 19.15, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.756 mg, 3.37 µmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (25 mg, 0.07 mmol), [Reactants], 1-bromo-4-fluorobenzene (9.24 µl, 0.08 mmol) and cesium carbonate (32.9 mg, 0.10 mmol) dissolved in 1,4-dioxane (1.5 ml). The resultin... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3af268f385e348b58c53e9a70feadd8e | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC=C1F)Br.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][C... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1 | CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 49.47 | [{"value": 49.47, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (7.56 mg, 0.03 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (250 mg, 0.67 mmol), biphenyl-2-yldicyclohexylphosphine (23.59 mg, 0.07 mmol), 1-bromo-4-fluorobenzene (0.092 ml, 0.84 mmol) and cesium carbonate (329 mg, 1.01 mmol) di... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-02be984aa68b424aad9a285d9b990afb | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC=C1F)Br.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][C... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1 | CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 15.96 | [{"value": 15.96, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (1.511 mg, 6.73 µmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (50 mg, 0.13 mmol), biphenyl-2-yldicyclohexylphosphine (4.72 mg, 0.01 mmol), 1-bromo-4-fluorobenzene (0.018 ml, 0.17 mmol) and cesium carbonate (65.8 mg, 0.20 mmol) di... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3e57a399433c4f5aa6087180dd878e52 | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC=C1F)Br.CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[CH2:10][C... | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1 | CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 19.03 | [{"value": 19.03, "product": "CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.93 mg, 0.02 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (130 mg, 0.35 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.25 mg, 0.03 mmol), 1-bromo-4-fluorobenzene (0.048 ml, 0.44 mmol) and cesium carbonate... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CN(C)C(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1ccc(Br)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CN(C)C(=O)c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a7df51f0be0a4af98f3bfe87d6600255 | CCOC(=O)CN.Nc1cc(F)cnc1Br>>CCOC(=O)CNc1ncc(F)cc1N | C1=C(C=NC(=C1N)Br)F.CCOC(=O)CN.Cl>>CCOC(=O)CNC1=C(C=C(C=N1)F)N | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH2:7].Br[c:8]1[n:9][cH:10][c:11]([F:12])[cH:13][c:14]1[NH2:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][c:8]1[n:9][cH:10][c:11]([F:12])[cH:13][c:14]1[NH2:15] | CCOC(=O)CN.Nc1cc(F)cnc1Br | CCOC(=O)CNc1ncc(F)cc1N | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[NH2;D1;+0:12]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6] | 0 | [{"value": 0.0, "product": "CCOC(=O)CNC1=C(C=C(C=N1)F)N", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | In a 50 mL round-bottomed flask 2-bromo-5-fluoropyridin-3-amine (500 mg, 2.62 mmol) ethyl 2-aminoacetate hydrochloride (731 mg, 5.24 mmol) BINAP (163 mg, 0.26 mmol) palladium(II) acetate (58.8 mg, 0.26 mmol) CESIUM CARBONATE (2559 mg, 7.85 mmol) were taken.The solids were mixed well and degassed.The toluene was taken i... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CCOC(=O)CN.Nc1cc(F)cnc1Br>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)CNc1ncc(F)cc1N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-74ae5f362208460ebf2f7ad1b936b06b | CC(N)c1ccccc1.Clc1cnccn1>>CC(Nc1cnccn1)c1ccccc1 | C1=CN=C(C=N1)Cl.CC(C1=CC=CC=C1)N>>CC(C1=CC=CC=C1)NC2=NC=CN=C2 | [CH3:1][CH:2]([NH2:3])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.Cl[c:4]1[cH:5][n:6][cH:7][cH:8][n:9]1>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][n:6][cH:7][cH:8][n:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(N)c1ccccc1.Clc1cnccn1 | CC(Nc1cnccn1)c1ccccc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d8d76a4347a32a5acf79894f48887cf8d745ba4ca5f91e54084ebdbe25f43c75 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[C:8](-[NH2;D1;+0:9])-[c:10]>>[C;D1;H3:7]-[C:8](-[c:10])-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 42.54 | [{"value": 42.54, "product": "CC(C1=CC=CC=C1)NC2=NC=CN=C2", "details": "", "is_desired": true}] | 70 | CELSIUS | null | null | To a solution of 1-phenylethanamine (212 mg, 1.75 mmol) and 2-chloropyrazine (200 mg, 1.75 mmol) in toluene (10 mL) while bubbling N2 was added binap (141 mg, 0.23 mmol), sodium tert-butoxide (235 mg, 2.44 mmol) and palladium(II) acetate (51.0 mg, 0.23 mmol). The reaction mixure was heated at 70 oC for 3 hours. The rea... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnccn1 | c1cnccn1 | c1cnccn1.c1ccccc1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 70 | null | CC(N)c1ccccc1.Clc1cnccn1>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>CC(Nc1cnccn1)c1ccccc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0a36562a530a4f6bb99c0bf4c44fc018 | CS(=O)(=O)c1ccc(N)cc1.Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1>>Cc1ccc(Oc2ccnc(Nc3ccc(S(C)(=O)=O)cc3)c2)c(C)n1 | CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C.CS(=O)(=O)C1=CC=C(C=C1)N>>CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)C)C | [NH2:12][c:13]1[cH:14][cH:15][c:16]([S:17]([CH3:18])(=[O:19])=[O:20])[cH:21][cH:22]1.Cl[c:11]1[n:10][cH:9][cH:8][c:7]([O:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:26][c:24]2[CH3:25])[cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([S:17]([CH3:18])(=[O:19])=[O:20... | CS(=O)(=O)c1ccc(N)cc1.Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1 | Cc1ccc(Oc2ccnc(Nc3ccc(S(C)(=O)=O)cc3)c2)c(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Oc3cccnc3)ccn2)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] | 50.82 | [{"value": 50.82, "product": "CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 10 mL microwave reactor 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (100 mg, 0.43 mmol) and 4-(methylsulfonyl)aniline (73.0 mg, 0.43 mmol) were dissolved in DMA (3 mL) to give a tan solution.To the resultant solution Cesium carbonate (0.068 mL, 0.85 mmol) was added and sparged with nitrogen for 1 minute. Then... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | 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].CC(=O)N(C)C | 150 | null | CS(=O)(=O)c1ccc(N)cc1.Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Cc1ccc(Oc2ccnc(Nc3ccc(S(C)(=O)=O)cc3)c2)c(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7897aa67f78748769844b414acdceeae | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(=O)(=O)NCCN2CCOCC2)cc1>>Cc1ccc(Oc2ccnc(Nc3ccc(S(=O)(=O)NCCN4CCOCC4)cc3)c2)c(C)n1 | CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C.C1COCCN1CCNS(=O)(=O)C2=CC=C(C=C2)N>>CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)NCCN4CCOCC4)C | Cl[c:11]1[n:10][cH:9][cH:8][c:7]([O:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:34][c:32]2[CH3:33])[cH:31]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([S:17](=[O:18])(=[O:19])[NH:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[cH:29][cH:30]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:1... | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(=O)(=O)NCCN2CCOCC2)cc1 | Cc1ccc(Oc2ccnc(Nc3ccc(S(=O)(=O)NCCN4CCOCC4)cc3)c2)c(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=S(=O)(NCCN1CCOCC1)c1ccc(Nc2cc(Oc3cccnc3)ccn2)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] | 60.66 | [{"value": 60.66, "product": "CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)NCCN4CCOCC4)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 10 mL microwave reactor 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (100 mg, 0.43 mmol) and 4-amino-N-(2-morpholinoethyl)benzenesulfonamide (122 mg, 0.43 mmol) were dissolved in DMA (5 mL) to give a tan solution.To the resultant solution Cesium carbonate (0.068 mL, 0.85 mmol) was added and sparged with nitrog... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1ccccc1.C1COCC[NH]1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 150 | null | Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1.Nc1ccc(S(=O)(=O)NCCN2CCOCC2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>Cc1ccc(Oc2ccnc(Nc3ccc(S(=O)(=O)NCCN4CCOCC4)cc3)c2)c(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-067637c197bb4672875d64a38b7940ee | COCC(C)NS(=O)(=O)c1ccc(N)cc1.Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1>>COCC(C)NS(=O)(=O)c1ccc(Nc2cc(Oc3ccc(C)nc3C)ccn2)cc1 | CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C.CC(COC)NS(=O)(=O)C1=CC=C(C=C1)N>>CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)NC(C)COC)C | [CH3:1][O:2][CH2:3][CH:4]([CH3:5])[NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:30][cH:31]1.Cl[c:15]1[cH:16][c:17]([O:18][c:19]2[cH:20][cH:21][c:22]([CH3:23])[n:24][c:25]2[CH3:26])[cH:27][cH:28][n:29]1>>[CH3:1][O:2][CH2:3][CH:4]([CH3:5])[NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([NH:14... | COCC(C)NS(=O)(=O)c1ccc(N)cc1.Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1 | COCC(C)NS(=O)(=O)c1ccc(Nc2cc(Oc3ccc(C)nc3C)ccn2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Oc3cccnc3)ccn2)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] | 51.97 | [{"value": 51.97, "product": "CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)NC(C)COC)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 10 mL microwave reactor 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (100 mg, 0.43 mmol) and 4-amino-N-(1-methoxypropan-2-yl)benzenesulfonamide (104 mg, 0.43 mmol) were dissolved in DMA (3 mL) to give a brown solution.To the resultant solution Cesium carbonate (0.068 mL, 0.85 mmol) was added and sparged with n... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C | 150 | null | COCC(C)NS(=O)(=O)c1ccc(N)cc1.Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC(=O)N(C)C>COCC(C)NS(=O)(=O)c1ccc(Nc2cc(Oc3ccc(C)nc3C)ccn2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bbf1fab9fbf9435cba74991837eb9bf4 | COc1ccc(I)cc1Br.NCC1CCOCC1>>COc1ccc(NCC2CCOCC2)cc1Br | COC1=C(C=C(C=C1)I)Br.C1COCCC1CN>>COC1=C(C=C(C=C1)NCC2CCOCC2)Br | I[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]([Br:17])[cH:15]1.[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][c:16]1[Br:17] | COc1ccc(I)cc1Br.NCC1CCOCC1 | COc1ccc(NCC2CCOCC2)cc1Br | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2CCOCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 10.42 | [{"value": 10.42, "product": "COC1=C(C=C(C=C1)NCC2CCOCC2)Br", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Palladium (II) acetate (0.032 g, 0.14 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.179 g, 0.29 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 2-bromo-4-iodo-1-methoxybenzene (0.6 g, 1.92 mmol), (tetrahydro-2H-pyr... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCOCC1 | HI | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | COc1ccc(I)cc1Br.NCC1CCOCC1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1ccc(NCC2CCOCC2)cc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6117c2ee846f49c3a77484ecf172e880 | COc1ccc(I)cc1Br.NCC1CCOCC1>>COc1ccc(NCC2CCOCC2)cc1Br | COC1=C(C=C(C=C1)I)Br.C1COCCC1CN>>COC1=C(C=C(C=C1)NCC2CCOCC2)Br | I[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]([Br:17])[cH:15]1.[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][c:16]1[Br:17] | COc1ccc(I)cc1Br.NCC1CCOCC1 | COc1ccc(NCC2CCOCC2)cc1Br | 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] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2CCOCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "COC1=C(C=C(C=C1)NCC2CCOCC2)Br", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Palladium (II) acetate (0.075 g, 0.34 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.223 g, 0.36 mmol) were suspended in dioxane (5mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 2-bromo-4-iodo-1-methoxybenzene (1.4 g, 4.47 mmol), (tetrahydro-2H-pyra... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCOCC1 | HI | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | COc1ccc(I)cc1Br.NCC1CCOCC1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(NCC2CCOCC2)cc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5211120ee16b4ae79338b46c711839b3 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C1=CC(=CC(=C1)Br)F.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:20]2[o:21][c:22]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[cH:29][c:30](=[O:31])[c:32]2[cH:33]1.Br[c:13]1[cH:14][cH:15][cH:16][c:17]([F:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][N:12]... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 70.85 | [{"value": 70.85, "product": "COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (0.045 g, 0.20 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (1.8 g, 5.02 mmol), methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (1.8 g, 5.02 mmol) and cesium carbonate (2.455 g, 7.53 mmol) dissolved in 1,4-diox... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.Fc1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cccc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-62d2a6fe53094d4f9d23ca6c92514364 | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.COc1cccc(Br)c1>>COC(=O)c1cc(C2CCCN2c2cccc(OC)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | COC1=CC(=CC=C1)Br.COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4>>COC1=CC=CC(=C1)N2CCCC2C3=CC(=CC4=C3OC(=CC4=O)N5CCOCC5)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[c:21]2[o:22][c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31](=[O:32])[c:33]2[cH:34]1.Br[c:13]1[cH:14][cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:1... | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.COc1cccc(Br)c1 | COC(=O)c1cc(C2CCCN2c2cccc(OC)c2)c2oc(N3CCOCC3)cc(=O)c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(N2CCOCC2)oc2c(C3CCCN3c3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 55.55 | [{"value": 55.55, "product": "COC1=CC=CC(=C1)N2CCCC2C3=CC(=CC4=C3OC(=CC4=O)N5CCOCC5)C(=O)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (3.13 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (125 mg, 0.35 mmol), 1-bromo-3-methoxybenzene (0.049 ml, 0.38 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.15 mg, 0.03 mmol) and cesium carbonate (170... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1.COc1cccc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(C2CCCN2c2cccc(OC)c2)c2oc(N3CCOCC3)cc(=O)c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cf737b8f3d9340aca6130b04f75e7c21 | Brc1ccc(Br)cc1.COC(=O)CN1CCNCC1>>COC(=O)CN1CCN(c2ccc(Br)cc2)CC1 | C1=CC(=CC=C1Br)Br.COC(=O)CN1CCNCC1>>COC(=O)CN1CCN(CC1)C2=CC=C(C=C2)Br | Br[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][NH:9][CH2:17][CH2:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | Brc1ccc(Br)cc1.COC(=O)CN1CCNCC1 | COC(=O)CN1CCN(c2ccc(Br)cc2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | 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": "COC(=O)CN1CCN(CC1)C2=CC=C(C=C2)Br", "details": "", "is_desired": true}] | 85 | CELSIUS | null | null | In a reaction vial, 1,4-dibromobenzene (0.373 g, 1.58 mmol), methyl 2-(piperazin-1-yl)acetate (0.100 g, 0.63 mmol), CS2CO3 (0.309 g, 0.95 mmol), and BINAP (0.024 g, 0.04 mmol) were taken up in 1,4-dioxane (1.5 ml). Argon was bubbled through the solution for 1 minute. Pd2(dba)3 (0.012 g, 0.01 mmol) was added, followed b... | 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 | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 85 | null | Brc1ccc(Br)cc1.COC(=O)CN1CCNCC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>COC(=O)CN1CCN(c2ccc(Br)cc2... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-498c0c75d66a47609408cbfbddaef8e5 | COC(=O)C1CCNCC1.Cc1cc(Br)ccc1F>>COC(=O)C1CCN(c2ccc(F)c(C)c2)CC1 | CC1=C(C=CC(=C1)Br)F.COC(=O)C1CCNCC1>>CC1=C(C=CC(=C1)N2CCC(CC2)C(=O)OC)F | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][NH:8][CH2:17][CH2:18]1.Br[c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([CH3:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([CH3:15])[cH:16]2)[CH2:17][CH2:18]1 | COC(=O)C1CCNCC1.Cc1cc(Br)ccc1F | COC(=O)C1CCN(c2ccc(F)c(C)c2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 0 | [{"value": 0.0, "product": "CC1=C(C=CC(=C1)N2CCC(CC2)C(=O)OC)F", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | In a 100 mL round-bottomed flask methyl piperidine-4-carboxylate (2.2 g, 15.36 mmol),4-bromo-1-fluoro-2-methylbenzene (1.954 mL, 15.36 mmol),Pd2(dba)3 (0.521 g, 0.57 mmol),BINAP (0.574 g, 0.92 mmol) and sodium tert-butoxide (4.43 g, 46.09 mmol) was taken in toluene (10 mL) under N2.The resulting reaction was stirred at... | 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 | 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 | COC(=O)C1CCNCC1.Cc1cc(Br)ccc1F>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COC(=O)C1CCN(c2ccc(F)c(C)c2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ce627b9c98e74957a0959e5bb6499f88 | CC(C)(C)OC(=O)N1CCNCC1.CN1Cc2ccc(Br)cc2C1=O>>CN1Cc2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2C1=O | CN1CC2=C(C1=O)C=C(C=C2)Br.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC3=C(CN(C3=O)C)C=C2 | [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]2[c:22]([cH:21]1)[C:23](=[O:24])[N:2]([CH3:1])[CH2:3]2>>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]... | CC(C)(C)OC(=O)N1CCNCC1.CN1Cc2ccc(Br)cc2C1=O | CN1Cc2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2C1=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 | Ullmann-Goldberg Substitution amine | efe95ec4c413493be875dc512aab69a44738654b4e62597e286ea7eb8b5ca48f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C1NCc2ccc(N3CCNCC3)cc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[#7:6]):[c:7]:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7:6]-[C:4](=[O;D1;H0:5])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[#7:9]-[C:10]-[C:11]-1):[c:7]:[c:8] | 57.03 | [{"value": 57.03, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC3=C(CN(C3=O)C)C=C2", "details": "", "is_desired": true}] | 60 | CELSIUS | null | null | In an oven-dried RB flask was added Tris(dibenzylideneacetone)dipalladium(0) (0.046 g, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.062 g, 0.10 mmol). The flask was evacuated and back-filled with nitrogen. Anhydrous toluene (3 mL) was added and the mixture was stirred at rt for 10 min to give a pur... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1C[NH]CC[NH]1 | c1ccc2c(c1)C[NH]C2.C1C[NH]CC[NH]1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 60 | null | CC(C)(C)OC(=O)N1CCNCC1.CN1Cc2ccc(Br)cc2C1=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>CN1Cc2ccc(N3CCN(C(=... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b1c7bfb9b1414262b689b975ba465d86 | C1COCCN1.Clc1ccc(Br)c(Cl)n1>>Clc1ccc(N2CCOCC2)c(Cl)n1 | C1=CC(=NC(=C1Br)Cl)Cl.C1COCCN1>>C1COCCN1C2=C(N=C(C=C2)Cl)Cl | [NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.Br[c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:14][c:12]1[Cl:13]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[c:12]([Cl:13])[n:14]1 | C1COCCN1.Clc1ccc(Br)c(Cl)n1 | Clc1ccc(N2CCOCC2)c(Cl)n1 | 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] | CC(C)(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1 | 0 | [{"value": 0.0, "product": "C1COCCN1C2=C(N=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 25 | CELSIUS | null | null | 2011-05-18 r1 was checked by NMR and LC/MS: Vial a: 3-bromo-2,6-dichloropyridine (0.023 g, .1 mmol), morpholine (9.15 µl, 0.11 mmol), Pd2dba3 (1.831 mg, 2.00 µmol),4-(2,6-dichloropyridin-3-yl)morpholine (0.00 µg) were mixed in tBuOH (0.241 ml) in microwave vial. The vial was flushed with N2 and sealed and the mix wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].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].CC(C)(C)O | 25 | null | C1COCCN1.Clc1ccc(Br)c(Cl)n1>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].CC(C)(C)O>Clc1ccc(N2CCOCC2)c(Cl)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7a326b6af66842839478f845f091880c | C1COCCN1.Clc1ccc(Br)c(Cl)n1>>Clc1ccc(N2CCOCC2)c(Cl)n1 | C1=CC(=NC(=C1Br)Cl)Cl.C1COCCN1>>C1COCCN1C2=C(N=C(C=C2)Cl)Cl | [NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.Br[c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:14][c:12]1[Cl:13]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[c:12]([Cl:13])[n:14]1 | C1COCCN1.Clc1ccc(Br)c(Cl)n1 | Clc1ccc(N2CCOCC2)c(Cl)n1 | CC(C)(C)[O-].[Na+] | 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] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1 | 0 | [{"value": 0.0, "product": "C1COCCN1C2=C(N=C(C=C2)Cl)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | sodium tert-butoxide (0.012 g, 0.13 mmol), were transfered to a microwave vial. Pd2dba3 (0.916 mg, 1.00 µmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.933 mg, 2.00 µmol), (2-DICYCLOHEXYLPHOSPHINO-2',6'-DIISOPROPYL-1,1'-BIPHENYL)[2-(2-AMINOETHYL)PHENYL]PALLADIUM(II) (0.729 mg, 1.00 µmol) were added.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].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].C1CCOC1 | 100 | null | C1COCCN1.Clc1ccc(Br)c(Cl)n1>CC(C)(C)[O-].[Na+].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].C1CCOC1>Clc1ccc(N2CCOCC2)c(Cl)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-74d98b785957480d946a0d3ab89bccf5 | C1CC2(CCN1)OCCO2.COc1cccc(Br)n1>>COc1cccc(N2CCC3(CC2)OCCO3)n1 | COC1=NC(=CC=C1)Br.C1CNCCC12OCCO2>>COC1=CC=CC(=N1)N2CCC3(CC2)OCCO3 | [NH:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[O:14][CH2:15][CH2:16][O:17]2.Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[n:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][C:11]3([CH2:12][CH2:13]2)[O:14][CH2:15][CH2:16][O:17]3)[n:18]1 | C1CC2(CCN1)OCCO2.COc1cccc(Br)n1 | COc1cccc(N2CCC3(CC2)OCCO3)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.CC(=O)O.CC(=O)O.[Pd] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 98501ed119dbc1fd4801d293f69e3d6501dd1371a251bfd1836b1cb54df9f3d3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCC3(CC2)OCCO3)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 69.11 | [{"value": 69.11, "product": "COC1=CC=CC(=N1)N2CCC3(CC2)OCCO3", "details": "", "is_desired": true}] | null | CELSIUS | null | null | The same procedure as EN03653-93-01. | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CC2(CCN1)OCCO2.c1ccncc1 | c1ccncc1.C1CC2(CC[NH]1)OCCO2 | c1ccncc1.C1CC2(CC[NH]1)OCCO2 | 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] | null | null | C1CC2(CCN1)OCCO2.COc1cccc(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.CC(=O)O.CC(=O)O.[Pd]>COc1cccc(N2CCC3(CC2)OCCO3)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c6d710180f5249588ab02dc546a2ae67 | COC(=O)c1cc(Br)cc(Br)c1.Nc1ccccc1>>COC(=O)c1cc(Br)cc(Nc2ccccc2)c1 | COC(=O)C1=CC(=CC(=C1)Br)Br.C1=CC=C(C=C1)N>>COC(=O)C1=CC(=CC(=C1)Br)NC2=CC=CC=C2 | Br[c:10]1[cH:9][c:7]([Br:8])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | COC(=O)c1cc(Br)cc(Br)c1.Nc1ccccc1 | COC(=O)c1cc(Br)cc(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.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:[c:8] | 0 | [{"value": 0.0, "product": "COC(=O)C1=CC(=CC(=C1)Br)NC2=CC=CC=C2", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | aniline (0.380 g, 4.08 mmol), methyl 3,5-dibromobenzoate (1.000 g, 3.40 mmol), Pd(OAc)2 (0.076 g, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.295 g, 0.51 mmol) and CESIUM CARBONATE (1.663 g, 5.10 mmol) were stirred in toluene (10 mL) and degassed with nitrogen for 15 minutes. The mixture wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | COC(=O)c1cc(Br)cc(Br)c1.Nc1ccccc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=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>COC(=O)c1cc(Br)cc(Nc2ccccc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e2f4bb7b7a8a4f84a94e64c143c99234 | COC(=O)c1ccc(Br)cc1.NCc1cc(F)cc(F)c1>>COC(=O)c1ccc(NCc2cc(F)cc(F)c2)cc1 | COC(=O)C1=CC=C(C=C1)Br.C1=C(C=C(C=C1F)F)CN>>COC(=O)C1=CC=C(C=C1)NCC2=CC(=CC(=C2)F)F | Br[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20][cH:19]1.[NH2:9][CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]2)[cH:19][cH:20]1 | COC(=O)c1ccc(Br)cc1.NCc1cc(F)cc(F)c1 | COC(=O)c1ccc(NCc2cc(F)cc(F)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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "COC(=O)C1=CC=C(C=C1)NCC2=CC(=CC(=C2)F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | methyl 4-bromobenzoate (1 g, 4.65 mmol), (3,5-difluorophenyl)methanamine (1.100 mL, 9.30 mmol) and Cesium carbonate (1.515 g, 4.65 mmol) were mixed in toluene (4 mL) and degassed by bubbling nitrogen through solution. Palladium acetate (0.052 g, 0.23 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.203 g, 0... | 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+].C1=CC=C(C=C1)P(C2=CC=CC=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 | COC(=O)c1ccc(Br)cc1.NCc1cc(F)cc(F)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COC(=O)c1ccc(NCc2cc(F)cc(F)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a50a848eea9042a19d3b9efbefd39662 | COC(=O)c1ccc(Br)cc1.NCc1cc(F)cc(F)c1>>COC(=O)c1ccc(NCc2cc(F)cc(F)c2)cc1 | COC(=O)C1=CC=C(C=C1)Br.C1=C(C=C(C=C1F)F)CN>>COC(=O)C1=CC=C(C=C1)NCC2=CC(=CC(=C2)F)F | Br[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20][cH:19]1.[NH2:9][CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]2)[cH:19][cH:20]1 | COC(=O)c1ccc(Br)cc1.NCc1cc(F)cc(F)c1 | COC(=O)c1ccc(NCc2cc(F)cc(F)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 | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "COC(=O)C1=CC=C(C=C1)NCC2=CC(=CC(=C2)F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | methyl 4-bromobenzoate (1.8 g, 8.37 mmol), (3,5-difluorophenyl)methanamine (1.980 mL, 16.74 mmol) and Cesium carbonate (2.73 g, 8.37 mmol) were mixed in toluene (4 mL) and degassed by bubbling nitrogen through solution. Palladium acetate (0.094 g, 0.42 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.365 g,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=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 | COC(=O)c1ccc(Br)cc1.NCc1cc(F)cc(F)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COC(=O)c1ccc(NCc2cc(F)cc(F)c2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d7ba527a2d2d4d7591368f0e50bee26a | COC(=O)c1ccc(Br)cc1.c1ccc2c(c1)CCNC2>>COC(=O)c1ccc(N2CCc3ccccc3C2)cc1 | COC(=O)C1=CC=C(C=C1)Br.C1CNCC2=CC=CC=C21>>COC(=O)C1=CC=C(C=C1)N2CCC3=CC=CC=C3C2 | Br[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20][cH:19]1.[NH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH2:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH2:18]2)[cH:19][cH:20]1 | COC(=O)c1ccc(Br)cc1.c1ccc2c(c1)CCNC2 | COC(=O)c1ccc(N2CCc3ccccc3C2)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 | 591571868c9d18da479269f364adcad64546c6d5dee00603a0cda86be0f16f6e | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc3C2)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] | 0 | [{"value": 0.0, "product": "COC(=O)C1=CC=C(C=C1)N2CCC3=CC=CC=C3C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | methyl 4-bromobenzoate (100 mg, 0.47 mmol), [Reactants] and Cesium carbonate (152 mg, 0.47 mmol) were mixed in toluene (4 mL) and degassed by bubbling nitrogen through solution. Palladium acetate (5.22 mg, 0.02 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (20.27 mg, 0.03 mmol) were added and the vial was c... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CCNC2 | c1ccccc1.c1ccc2c(c1)CC[NH]C2 | c1ccccc1.c1ccc2c(c1)CC[NH]C2 | 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 | COC(=O)c1ccc(Br)cc1.c1ccc2c(c1)CCNC2>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COC(=O)c1ccc(N2CCc3ccccc3C2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b03de5e7ee154175b8ccb76d7202e229 | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Nc1ccc(-n2ccnc2)cc1>>CN1CC(c2ccccc2)Oc2nc(Nc3ccc(-n4ccnc4)cc3)ccc2C1=O | CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3.C1=CC(=CC=C1N)N2C=CN=C2>>CN1CC(OC2=C(C1=O)C=CC(=N2)NC3=CC=C(C=C3)N4C=CN=C4)C5=CC=CC=C5 | Cl[c:14]1[n:13][c:12]2[c:29]([cH:28][cH:27]1)[C:30](=[O:31])[N:2]([CH3:1])[CH2:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[O:11]2.[NH2:15][c:16]1[cH:17][cH:18][c:19](-[n:20]2[cH:21][cH:22][n:23][cH:24]2)[cH:25][cH:26]1>>[CH3:1][N:2]1[CH2:3][CH:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[O:11][c:12]2[n:13][c:14]([NH... | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Nc1ccc(-n2ccnc2)cc1 | CN1CC(c2ccccc2)Oc2nc(Nc3ccc(-n4ccnc4)cc3)ccc2C1=O | 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] | 37.83 | [{"value": 37.83, "product": "CN1CC(OC2=C(C1=O)C=CC(=N2)NC3=CC=C(C=C3)N4C=CN=C4)C5=CC=CC=C5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (115 mg, 0.40 mmol), 4-(1H-imidazol-1-yl)aniline (95 mg, 0.60 mmol), PdOAc2 (8.94 mg, 0.04 mmol), biphenyl-2-yldicyclohexylphosphine (13.96 mg, 0.04 mmol) and CS2CO3 (389 mg, 1.19 mmol) were placed in a microwave vial equipped with a stirring ba... | 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.Nc1ccc(-n2ccnc2)cc1>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>CN1CC(c2ccccc2)Oc2nc(Nc3ccc(-n4ccnc4)cc3)ccc2C1=O |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f93da8755d504800bf04ba573750bf86 | C1COCCN1.COC(=O)c1cc(Br)cc2c1nc(C)n2Cc1cccc(C(F)(F)F)c1C>>COC(=O)c1cc(N2CCOCC2)cc2c1nc(C)n2Cc1cccc(C(F)(F)F)c1C | CC1=C(C=CC=C1C(F)(F)F)CN2C(=NC3=C(C=C(C=C32)Br)C(=O)OC)C.C1COCCN1>>CC1=C(C=CC=C1C(F)(F)F)CN2C(=NC3=C(C=C(C=C32)N4CCOCC4)C(=O)OC)C | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:16]2[c:15]([cH:14]1)[n:20]([CH2:21][c:22]1[cH:23][cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[c:31]1[CH3:32])[c:18]([CH3:19])[n:17]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13... | C1COCCN1.COC(=O)c1cc(Br)cc2c1nc(C)n2Cc1cccc(C(F)(F)F)c1C | COC(=O)c1cc(N2CCOCC2)cc2c1nc(C)n2Cc1cccc(C(F)(F)F)c1C | CC(C)(C)[O-].[K+] | CCCCP(CCCC)CCCC.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad72a931ae26909440432ecfbc99a97aacd5588f6be724598dc2f1340b152551 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Cn2cnc3ccc(N4CCOCC4)cc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:2:[c:9](-[C:10](-[#8:11])=[O;D1;H0:12]):[c:13]:1.[#8:14]1-[C:15]-[C:16]-[NH;D2;+0:17]-[C:18]-[C:19]-1>>[#8:11]-[C:10](=[O;D1;H0:12])-[c:9]1:[c:13]:[c;H0;D3;+0:1](-[N;H0;D3;+0:17]2-[C:18]-[C:19]-[#8:14]-[C:15]-[C:16]-2):[c:2]:[c:3]2:[#7;a:4](-[C:5]):[... | 0 | [{"value": 0.0, "product": "CC1=C(C=CC=C1C(F)(F)F)CN2C(=NC3=C(C=C(C=C32)N4CCOCC4)C(=O)OC)C", "details": "", "is_desired": true}] | null | CELSIUS | null | null | methyl 6-bromo-2-methyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazole-4-carboxylate (441 mg, 1.00 mmol) was taken up with morpholine (435 µl, 5.00 mmol), potassium tert-butoxide (449 mg, 4.00 mmol), tri-n-butylphosphine (49.3 µl, 0.2 mmol) and palladium(II) acetate (22.44 mg, 0.10 mmol) in dioxane (10ml) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccc2nc[nH]c2c1 | C1COCC[NH]1.c1ccc2[nH]cnc2c1 | C1COCC[NH]1.c1ccc2[nH]cnc2c1.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].CCCCP(CCCC)CCCC.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | null | null | C1COCCN1.COC(=O)c1cc(Br)cc2c1nc(C)n2Cc1cccc(C(F)(F)F)c1C>CC(C)(C)[O-].[K+].CCCCP(CCCC)CCCC.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COC(=O)c1cc(N2CCOCC2)cc2c1nc(C)n2Cc1cccc(C(F)(F)F)c1C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-006fb353766e418abd7ffca7f96dda71 | CCOC(=O)c1cnc(N)o1.FC(F)(F)c1cccc(Cl)n1>>CCOC(=O)c1cnc(Nc2cccc(C(F)(F)F)n2)o1 | C1=CC(=NC(=C1)Cl)C(F)(F)F.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=CC=CC(=N2)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][cH:14][c:15]([C:16]([F:17])([F:18])[F: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][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20]2)[o:21]1 | CCOC(=O)c1cnc(N)o1.FC(F)(F)c1cccc(Cl)n1 | CCOC(=O)c1cnc(Nc2cccc(C(F)(F)F)n2)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 | 67.78 | [{"value": 67.78, "product": "CCOC(=O)C1=CN=C(O1)NC2=CC=CC(=N2)C(F)(F)F", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: To test substrate scope in 5-ester substituted 2-aminooxazole coupling. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol), cesium carbonate (651 mg, 2.00 mmol), ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol... | 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)c1cccc(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>CCOC(=O)c1cnc(Nc2cccc(C(F)(F... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8c2a9ba6590649f9b70909d38908193a | CCOC(=O)c1cnc(N)o1.N#Cc1ccnc(Cl)c1>>CCOC(=O)c1cnc(Nc2cc(C#N)ccn2)o1 | C1=CN=C(C=C1C#N)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)C#N | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:19]1.Cl[c:11]1[cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17][n:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17][n:18]2)[o:19]1 | CCOC(=O)c1cnc(N)o1.N#Cc1ccnc(Cl)c1 | CCOC(=O)c1cnc(Nc2cc(C#N)ccn2)o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncco2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH2;D1;+0:12]):[#7;a:13]:[c:14]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#8;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:13]:[c:14]:1 | 60.08 | [{"value": 60.08, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)C#N", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: To test substrate scope in 5-ester substituted 2-aminooxazole coupling. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol), cesium carbonate (651 mg, 2.00 mmol), ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol... | 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.N#Cc1ccnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cnc(Nc2cc(C#N)ccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-43f679e964f04e22b49e850c529e3849 | CCOC(=O)c1cnc(N)o1.Clc1ccccn1>>CCOC(=O)c1cnc(Nc2ccccn2)o1 | C1=CC=NC(=C1)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=CC=CC=N2 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:17]1.Cl[c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]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][cH:14][cH:15][n:16]2)[o:17]1 | CCOC(=O)c1cnc(N)o1.Clc1ccccn1 | CCOC(=O)c1cnc(Nc2ccccn2)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 | 37.77 | [{"value": 37.77, "product": "CCOC(=O)C1=CN=C(O1)NC2=CC=CC=N2", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: To test the substrate scope in 5-ester substituted 2-aminooxazole coupling. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol), cesium carbonate (651 mg, 2.00 mmol), ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 ... | 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.Clc1ccccn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=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(Nc2ccccn2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-99625d03cee6403dbb604294d8ab8a9b | CCOC(=O)c1cnc(N)o1.O=[N+]([O-])c1ccc(Cl)nc1>>CCOC(=O)c1cnc(Nc2ccc([N+](=O)[O-])cn2)o1 | C1=CC(=NC=C1[N+](=O)[O-])Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC=C(C=C2)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:20]1.Cl[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][n:19]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]([N+:15](=[O:16])[O-:17])[cH:18][n:19]2)[o:20]1 | CCOC(=O)c1cnc(N)o1.O=[N+]([O-])c1ccc(Cl)nc1 | CCOC(=O)c1cnc(Nc2ccc([N+](=O)[O-])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 | 85.62 | [{"value": 85.62, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC=C(C=C2)[N+](=O)[O-]", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Objective: Test of substrate scope in couple of ester substituted aminooxazole To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol) 2-chloro-5-nitropyridine (158 mg, 1.00 mm... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cocn1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 160 | null | CCOC(=O)c1cnc(N)o1.O=[N+]([O-])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([N+... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-daeef600c38146b5994b548902e1f20b | Fc1ccc(Br)cc1.O=C(c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1)N1CCOCC1>>O=C(c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1)N1CCOCC1 | C1=CC(=CC=C1F)Br.C1CC(NC1)C2=CC(=CC3=C2OC(=CC3=O)N4CCOCC4)C(=O)N5CCOCC5>>C1CC(N(C1)C2=CC=C(C=C2)F)C3=CC(=CC4=C3OC(=CC4=O)N5CCOCC5)C(=O)N6CCOCC6 | Br[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1.[O:1]=[C:2]([c:3]1[cH:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][NH:10]2)[c:18]2[o:19][c:20]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[cH:27][c:28](=[O:29])[c:30]2[cH:31]1)[N:32]1[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1>>[O:1]=[C:2]([c:3]1[cH:4][c:5]([CH:6]2[CH2:7][CH... | Fc1ccc(Br)cc1.O=C(c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1)N1CCOCC1 | O=C(c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1)N1CCOCC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1cc(C2CCCN2c2ccccc2)c2oc(N3CCOCC3)cc(=O)c2c1)N1CCOCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[#8;a:6]:[c:7]:[c:8]-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 45.62 | [{"value": 45.62, "product": "C1CC(N(C1)C2=CC=C(C=C2)F)C3=CC(=CC4=C3OC(=CC4=O)N5CCOCC5)C(=O)N6CCOCC6", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | diacetoxypalladium (6.79 mg, 0.03 mmol) was added to a stirred mixture of 6-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one (250 mg, 0.60 mmol), biphenyl-2-yldicyclohexylphosphine (21.19 mg, 0.06 mmol), 1-bromo-4-fluorobenzene (0.083 ml, 0.76 mmol) and cesium carbonate (296 mg, 0.91 mmol) diss... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Fc1ccc(Br)cc1.O=C(c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1)N1CCOCC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>O=C(c1cc(C2CCCN2c2ccc(F)cc2)c2oc(N3CCOCC3)cc(=O)c2c1)N1CCOCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7137664b914247a99384dbf76411ea05 | CCOC(=O)c1ccc(Cl)nc1.CCOC(=O)c1cnc(N)o1>>CCOC(=O)c1ccc(Nc2ncc(C(=O)OCC)o2)nc1 | CCOC(=O)C1=CN=C(C=C1)Cl.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(C=C1)NC2=NC=C(O2)C(=O)OCC | Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:22][n:21]1.[NH2:10][c:11]1[n:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[o:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[o:20]2)[n:21][cH:22]1 | CCOC(=O)c1ccc(Cl)nc1.CCOC(=O)c1cnc(N)o1 | CCOC(=O)c1ccc(Nc2ncc(C(=O)OCC)o2)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 | 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 | 67.21 | [{"value": 67.21, "product": "CCOC(=O)C1=CN=C(C=C1)NC2=NC=C(O2)C(=O)OCC", "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), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(di... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cocn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 160 | null | CCOC(=O)c1ccc(Cl)nc1.CCOC(=O)c1cnc(N)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>CCOC(=O)c1ccc(Nc2ncc(C(=O)OC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0b0035404bff4099a5e08c9ac05b0329 | CCOC(=O)c1cnc(N)o1.N#Cc1cncc(Cl)n1>>CCOC(=O)c1cnc(Nc2cncc(C#N)n2)o1 | C1=C(N=C(C=N1)Cl)C#N.CCOC(=O)C1=CN=C(O1)N>>CCOC(=O)C1=CN=C(O1)NC2=NC(=CN=C2)C#N | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[o:19]1.Cl[c:11]1[cH:12][n:13][cH:14][c:15]([C:16]#[N:17])[n:18]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][n:13][cH:14][c:15]([C:16]#[N:17])[n:18]2)[o:19]1 | CCOC(=O)c1cnc(N)o1.N#Cc1cncc(Cl)n1 | CCOC(=O)c1cnc(Nc2cncc(C#N)n2)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 | d8d76a4347a32a5acf79894f48887cf8d745ba4ca5f91e54084ebdbe25f43c75 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc(Nc2ncco2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[#8;a:11]:[c:12](-[NH2;D1;+0:13]):[#7;a:14]:[c:15]:1>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[#8;a:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2):[#7;a:14]:[c:15]:1 | 46.72 | [{"value": 46.72, "product": "CCOC(=O)C1=CN=C(O1)NC2=NC(=CN=C2)C#N", "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), 6-chloropyrazine-2-carbonitrile (139 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnccn1 | c1cnccn1 | c1cocn1.c1cnccn1 | 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.N#Cc1cncc(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>CCOC(=O)c1cnc(Nc2cncc(C#N)n2)o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-57458b4fbe4c490eb3a4dddc522d1ef4 | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1>>Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 | CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NC=CN1C2=CC=C(C=C2)N>>CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C | Cl[c:12]1[cH:13][cH:14][c:15]2[c:16]([n:17]1)[O:18][CH:19]([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[CH2:26][N:27]([CH3:28])[C:29]2=[O:30].[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:31][cH:32]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14]... | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1 | Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 | 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] | 41.13 | [{"value": 41.13, "product": "CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (173 mg, 0.60 mmol), 4-(2-methyl-1H-imidazol-1-yl)aniline (125 mg, 0.72 mmol), PdOAc2 (13.47 mg, 0.06 mmol), biphenyl-2-yldicyclohexylphosphine (21.03 mg, 0.06 mmol) and cesium carbonate (489 mg, 1.50 mmol) were placed in a microwave vial equipp... | 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 | c1ncc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1>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>Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1df95b34548d48fe94a49234436e46e5 | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1>>Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 | CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NC=CN1C2=CC=C(C=C2)N>>CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C | Cl[c:12]1[cH:13][cH:14][c:15]2[c:16]([n:17]1)[O:18][CH:19]([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[CH2:26][N:27]([CH3:28])[C:29]2=[O:30].[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:31][cH:32]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14]... | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1 | Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 | 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] | 42.31 | [{"value": 42.31, "product": "CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C", "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) was added via a syringe and the mixture was heated to 100°C in a microwave apparatus for 1h. The reaction mixture was filtered, the solvent was evaporated and the residue was purified by HPLC to give 53 ... | 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 | c1ncc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1>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>Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b66bb670a88e49d4a4b3a67904494b50 | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1>>Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 | CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NC=CN1C2=CC=C(C=C2)N>>CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C | Cl[c:12]1[cH:13][cH:14][c:15]2[c:16]([n:17]1)[O:18][CH:19]([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[CH2:26][N:27]([CH3:28])[C:29]2=[O:30].[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:31][cH:32]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14]... | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1 | Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 | 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] | 74.93 | [{"value": 74.93, "product": "CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Not continued. | 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 | c1ncc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1>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>Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1e88fef4eebd41feb29f461d3c9c5a57 | COc1cc(F)ccc1-c1nc(Cl)ncc1F.CS(=O)(=O)Cc1cccc(N)c1>>COc1cc(F)ccc1-c1nc(Nc2cccc(CS(C)(=O)=O)c2)ncc1F | COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)Cl.CS(=O)(=O)CC1=CC(=CC=C1)N>>COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)NC3=CC=CC(=C3)CS(=O)(=O)C | Cl[c:12]1[n:11][c:10](-[c:9]2[c:3]([O:2][CH3:1])[cH:4][c:5]([F:6])[cH:7][cH:8]2)[c:27]([F:28])[cH:26][n:25]1.[NH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][S:20]([CH3:21])(=[O:22])=[O:23])[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1-[c:10]1[n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18](... | COc1cc(F)ccc1-c1nc(Cl)ncc1F.CS(=O)(=O)Cc1cccc(N)c1 | COc1cc(F)ccc1-c1nc(Nc2cccc(CS(C)(=O)=O)c2)ncc1F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 50.64 | [{"value": 50.64, "product": "COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)NC3=CC=CC(=C3)CS(=O)(=O)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (0.25 g, 0.97 mmol), 3-((methylsulfonyl)methyl)aniline (0.180 g, 0.97 mmol), cesium carbonate (1.270 g, 3.90 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.141 g, 0.24 mmol)and Pd2(dba)3 (0.178 g, 0.19 mmol) were suspended in degassed 1,4-dio... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | COc1cc(F)ccc1-c1nc(Cl)ncc1F.CS(=O)(=O)Cc1cccc(N)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>COc1cc(F)ccc1-c1n... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d5d09a4967464981aba1493aa54fbd9b | C1COCCN1.OCc1ccc(Br)cn1>>OCc1ccc(N2CCOCC2)cn1 | C1=CC(=NC=C1Br)CO.C1COCCN1>>C1COCCN1C2=CN=C(C=C2)CO | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.Br[c:6]1[cH:5][cH:4][c:3]([CH2:2][OH:1])[n:14][cH:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][n:14]1 | C1COCCN1.OCc1ccc(Br)cn1 | OCc1ccc(N2CCOCC2)cn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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 | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[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 | 19.36 | [{"value": 19.36, "product": "C1COCCN1C2=CN=C(C=C2)CO", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | In a 10 mL Microwave vial was (5-bromopyridin-2-yl)methanol (500 mg, 2.66 mmol), morpholine (0.233 mL, 2.66 mmol),cesium carbonate (2166 mg, 6.65 mmol), Pd2(dba)3 (60.9 mg, 0.07 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (115 mg, 0.20 mmol) in dioxane (10 mL) () to give a brown suspension. The ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | C1COCCN1.OCc1ccc(Br)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=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>OCc1ccc(N2CCOCC2)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5ffc5c4a730b4c9fa67430c9657da268 | C[C@@H]1CNCCN1.Fc1ccc(Br)c(C(F)(F)F)c1>>C[C@@H]1CN(c2ccc(F)cc2C(F)(F)F)CCN1 | C1=CC(=C(C=C1F)C(F)(F)F)Br.C[C@@H]1CNCCN1>>C[C@@H]1CN(CCN1)C2=C(C=C(C=C2)F)C(F)(F)F | [CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:16][CH2:17][NH:18]1.Br[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[CH2:16][CH2:17][NH:18]1 | C[C@@H]1CNCCN1.Fc1ccc(Br)c(C(F)(F)F)c1 | C[C@@H]1CN(c2ccc(F)cc2C(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 | d7148bc7995d5dfa1607e72989e75c64b789e6aafbd2cc3ab6637dcd843b0985 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1):[c:2]:[c:3] | 59 | [{"value": 59.0, "product": "C[C@@H]1CN(CCN1)C2=C(C=C(C=C2)F)C(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (5 g, 20.58 mmol), (R)-2-methylpiperazine (2.164 g, 21.61 mmol), sodium tert-butoxide (3.95 g, 41.15 mmol) and BINAP (0.512 g, 0.82 mmol) in anhydrous toluene (60 mL) was degassed under vacuum with inlet of nitrogen. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.377 g, 0.41 mmo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | C1CNCC[NH]1.c1ccccc1 | C1CNCC[NH]1.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 | 100 | null | C[C@@H]1CNCCN1.Fc1ccc(Br)c(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].CC1=CC=CC=C1>C[C@@H]1CN(c2ccc(F)cc2C(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d91c4f300cee41c898f5dc5506a9a9f7 | C[C@@H]1CNCCN1.Fc1ccc(Br)c(C(F)(F)F)c1>>C[C@@H]1CN(c2ccc(F)cc2C(F)(F)F)CCN1 | C1=CC(=C(C=C1F)C(F)(F)F)Br.C[C@@H]1CNCCN1>>C[C@@H]1CN(CCN1)C2=C(C=C(C=C2)F)C(F)(F)F | [CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:16][CH2:17][NH:18]1.Br[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[CH2:16][CH2:17][NH:18]1 | C[C@@H]1CNCCN1.Fc1ccc(Br)c(C(F)(F)F)c1 | C[C@@H]1CN(c2ccc(F)cc2C(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 | d7148bc7995d5dfa1607e72989e75c64b789e6aafbd2cc3ab6637dcd843b0985 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1):[c:2]:[c:3] | 59 | [{"value": 59.0, "product": "C[C@@H]1CN(CCN1)C2=C(C=C(C=C2)F)C(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (10 g, 41.15 mmol), (R)-2-methylpiperazine (4.33 g, 43.21 mmol), sodium tert-butoxide (7.91 g, 82.31 mmol) and BINAP (1.025 g, 1.65 mmol) in anhydrous toluene (100 mL) was degassed under vacuum with inlet of nitrogen. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.754 g, 0.82 mm... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | C1CNCC[NH]1.c1ccccc1 | C1CNCC[NH]1.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 | 100 | null | C[C@@H]1CNCCN1.Fc1ccc(Br)c(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].CC1=CC=CC=C1>C[C@@H]1CN(c2ccc(F)cc2C(... |
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