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-c31cb9b44c404c10ba3aa533aa079e2b | ord-6adc145dc9574a5abe15a17244a23aab | CCC(=O)C1CCOC1.Nc1ccc([N+](=O)[O-])cn1>>Cc1c(C2CCOC2)nc2ccc([N+](=O)[O-])cn12 | O1CC(CC1)C(CC)=O.NC1=NC=C(C=C1)[N+](=O)[O-]>>CC1=C(N=C2N1C=C(C=C2)[N+](=O)[O-])C2COCC2 | O=[C:3]([CH2:2][CH3:1])[CH:4]1[CH2:5][CH2:6][O:7][CH2:8]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6][O:7][CH2:8]2)[n:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]12 | CCC(=O)C1CCOC1.Nc1ccc([N+](=O)[O-])cn1 | Cc1c(C2CCOC2)nc2ccc([N+](=O)[O-])cn12 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | cbc7e6c5e0a09d2e514fd60fb099adf259bb478395dbd8e339a49821fedd9120 | 8182c33d66a1c51620dac2e3d5b839c3fec60d5b5668262efc6be8b10c115a58 | c1ccn2cc(C3CCOC3)nc2c1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;D1;H3:3])-[C:4](-[C:5])-[C:6]-[#8:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[#8:7]-[C:6]-[C:4](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c:9](:[c:10]):[n;H0;D3;+0:11](:[c:12]:[c:13]):[c;H0;D3;+0:2]:1-[C;D1;H3:3])-[C:5] | null | [] | null | null | null | null | Operations similar to Production Example 1-(1) were conducted using 1-tetrahydro-3-furanyl-1-propanone in place of 3-methyl-2-butanone, and successively those of Production Example 1-(2) were conducted using 2-amino-5-nitropyridine. The resulting solid was suspended in ethyl acetate, washed with saturated aqueous sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | C1CCOC1.c1ccn2ccnc2c1 | HO- | C(C)(=O)OCC | null | null | CCC(=O)C1CCOC1.Nc1ccc([N+](=O)[O-])cn1>C(C)(=O)OCC>Cc1c(C2CCOC2)nc2ccc([N+](=O)[O-])cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c35de7734a0408eaf9404625f6f2ad4 | Nc1ccc([N+](=O)[O-])cn1.O=C1CCCCC1Cl>>O=[N+]([O-])c1ccc2nc3c(n2c1)CCCC3 | ClC1C(CCCC1)=O.NC1=NC=C(C=C1)[N+](=O)[O-]>>[N+](=O)([O-])C=1C=CC2=NC3=C(N2C1)CCCC3 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[n:11][cH:12]1.O=[C:9]1[CH:10](Cl)[CH2:13][CH2:14][CH2:15][CH2:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]3[c:10]([n:11]2[cH:12]1)[CH2:13][CH2:14][CH2:15][CH2:16]3 | Nc1ccc([N+](=O)[O-])cn1.O=C1CCCCC1Cl | O=[N+]([O-])c1ccc2nc3c(n2c1)CCCC3 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 7b133ee0fb2f2591e32fd58418cd7b700f192a61eeb5c67e6d9e3075dc440d37 | 235fd48cd394ba1137abde2ba7484c051be6ffcae187060d6065fe5adf0e90a3 | c1ccn2c3c(nc2c1)CCCC3 | Cl-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6]-1=O.[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[c:12]:[c:11]:[n;H0;D3;+0:10]1:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]2:[c;H0;D3;+0:1]:1-[C:2]-[C:3]-[C:4]-[C:5]-2 | null | [] | null | null | null | null | Operations similar to Production Example 1-(2) were conducted using 2-chlorocyclohexanone and 2-amino-5-nitropyridine. The resulting solid was suspended in ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to provid... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Primary amine | null | c1ccncc1.C1CCCCC1 | c1ccn2c3c(nc2c1)CCCC3 | c1ccn2c3c(nc2c1)CCCC3 | HCl | C(C)(=O)OCC | null | null | Nc1ccc([N+](=O)[O-])cn1.O=C1CCCCC1Cl>C(C)(=O)OCC>O=[N+]([O-])c1ccc2nc3c(n2c1)CCCC3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5ba5118e66d4f648c4af2bcf4b47e4c | Cc1ccc(S(=O)(=O)Cl)cc1.Nc1ccc([N+](=O)[O-])cn1>>Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cn2)cc1 | N1=CC=CC=C1.NC1=NC=C(C=C1)[N+](=O)[O-].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CC1=CC=C(C=C1)S(=O)(=O)NC1=NC=C(C=C1)[N+](=O)[O-] | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1)(=[O:7])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]2)[cH:19][cH:20]1 | Cc1ccc(S(=O)(=O)Cl)cc1.Nc1ccc([N+](=O)[O-])cn1 | Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cn2)cc1 | null | null | O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 84f0a2c480e4021adb28613388cdf35ca03a8bd65bbdad356e160a1b94684976 | 2988afdf4a13d931f021994343ac8648c6e63ca3a4c0ba598a4b99bbffc001c8 | O=S(=O)(Nc1ccccn1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11])-[c:4](:[c:5]):[c:6] | 79.4 | [{"value": 79.4, "product": "CC1=CC=C(C=C1)S(=O)(=O)NC1=NC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A pyridine suspension (40 ml) containing 2-amino-5-nitropyridine (4.0 g) and p-toluenesulfonyl chloride (5.7 g) was stirred for a day and night at 100° C. The reaction liquid was poured in water (200 ml), the precipitated solid was recovered by filtration, and successively washed with water and diethyl ether by the ord... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccncc1 | HCl | O | 100 | null | Cc1ccc(S(=O)(=O)Cl)cc1.Nc1ccc([N+](=O)[O-])cn1>O>Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8faafe0a96540189e61256568c08fed | FC(F)(F)c1ccc(Br)cc1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | BrC1=CC=C(C=C1)C(F)(F)F.C(=O)(O)C1=CC=C(C=C1)B(O)O>>FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F | Br[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:19][cH:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | FC(F)(F)c1ccc(Br)cc1.O=C(O)c1ccc(B(O)O)cc1 | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 71 | [{"value": 71.0, "product": "FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a mixed solution of ethylene glycol dimethyl ether (400 ml)-2M aqueous sodium carbonate solution (80 ml), 4-bromobenzotrifluoride (5.0 g), 4-carboxyphenylboronic acid (3.9 g) and tetrakistriphenylphosphinepalladium (2.5 g) were added and stirred at 100° C. for a day and night. Concentrating the reaction liquid under... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | 100 | null | FC(F)(F)c1ccc(Br)cc1.O=C(O)c1ccc(B(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-75fa72349d064702bc2f10d81a0d521d | Cc1cc(C(=O)O)ccc1Br.OB(O)c1ccc(C(F)(F)F)cc1>>Cc1cc(C(=O)O)ccc1-c1ccc(C(F)(F)F)cc1 | FC(C1=CC=C(C=C1)B(O)O)(F)F.BrC1=C(C=C(C=C1)C(=O)O)C>>CC1=C(C=CC(=C1)C(=O)O)C1=CC=C(C=C1)C(F)(F)F | Br[c:10]1[c:2]([CH3:1])[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1 | Cc1cc(C(=O)O)ccc1Br.OB(O)c1ccc(C(F)(F)F)cc1 | Cc1cc(C(=O)O)ccc1-c1ccc(C(F)(F)F)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | Production Example 14 was repeated except that 4-(trifluoromethyl)phenylboronic acid and 4-bromo-3-methylbenzenecarboxylic acid were used, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | null | null | null | Cc1cc(C(=O)O)ccc1Br.OB(O)c1ccc(C(F)(F)F)cc1>>Cc1cc(C(=O)O)ccc1-c1ccc(C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c01d2bd09a234c93973e07e594693927 | O=C(O)c1ccc(Br)cc1F.OB(O)c1ccc(C(F)(F)F)cc1>>O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1F | FC(C1=CC=C(C=C1)B(O)O)(F)F.BrC1=CC(=C(C=C1)C(=O)O)F>>FC=1C=C(C=CC1C(=O)O)C1=CC=C(C=C1)C(F)(F)F | Br[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[c:19]([F:20])[cH:18]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]1[F:20] | O=C(O)c1ccc(Br)cc1F.OB(O)c1ccc(C(F)(F)F)cc1 | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1F | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | Production Example 14 was repeated except that 4-(trifluoromethyl)phenylboronic acid and 4-bromo-2-fluorobenzenecarboxylic acid were used, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | null | null | null | O=C(O)c1ccc(Br)cc1F.OB(O)c1ccc(C(F)(F)F)cc1>>O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-273cf6a0dc324d5bb169ee6b263492f1 | Brc1ccccn1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(-c2ccccn2)cc1 | C(=O)(O)C1=CC=C(C=C1)B(O)O.BrC1=NC=CC=C1>>N1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)O | Br[c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1.OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:15][cH:14]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[cH:14][cH:15]1 | Brc1ccccn1.O=C(O)c1ccc(B(O)O)cc1 | O=C(O)c1ccc(-c2ccccn2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | Production Example 14 was repeated except that 4-carboxyphenylboronic acid and 2-bromopyridine were used, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | null | null | null | Brc1ccccn1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(-c2ccccn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-219a172ed1f541e9964bc63f0fbf5490 | COC(=O)c1ccc(B(O)O)cc1.Cc1ccc(Br)nc1>>COC(=O)c1ccc(-c2ccc(C)cn2)cc1 | COC(=O)C1=CC=C(C=C1)B(O)O.BrC1=NC=C(C=C1)C>>CC=1C=CC(=NC1)C1=CC=C(C(=O)OC)C=C1 | OB(O)[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][cH:16]1.Br[c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][n:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[cH:14][n:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(B(O)O)cc1.Cc1ccc(Br)nc1 | COC(=O)c1ccc(-c2ccc(C)cn2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | Repeating the operations of Production Example 14 using 4-(methoxycarbonyl)phenylboronic acid and 2-bromo-5-methylpyridine, methyl 4-(5-methyl-2-pyridyl)benzoate was obtained. Hydrolyzing the same with 5N aqueous sodium hydroxide solution, the title compound was obtained as white solid.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | null | null | null | COC(=O)c1ccc(B(O)O)cc1.Cc1ccc(Br)nc1>>COC(=O)c1ccc(-c2ccc(C)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa062152557a40419e3d9d16e682ccd0 | COC(=O)c1ccc(B(O)O)cc1.Clc1ccc(Cl)nc1>>COC(=O)c1ccc(-c2ccc(Cl)cn2)cc1 | COC(=O)C1=CC=C(C=C1)B(O)O.ClC1=NC=C(C=C1)Cl>>ClC=1C=CC(=NC1)C1=CC=C(C(=O)OC)C=C1 | OB(O)[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][cH:16]1.Cl[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][n:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][n:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(B(O)O)cc1.Clc1ccc(Cl)nc1 | COC(=O)c1ccc(-c2ccc(Cl)cn2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | Repeating the operations of Production Example 14 using 4-(methoxycarbonyl)phenylboronic acid and 2,5-dichloropyridine, methyl 4-(5-chloro-2-pyridyl)benzoate was obtained. Hydrolyzing the same with 5N aqueous sodium hydroxide solution, the title compound was obtained as white solid.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HCl.B | null | null | null | COC(=O)c1ccc(B(O)O)cc1.Clc1ccc(Cl)nc1>>COC(=O)c1ccc(-c2ccc(Cl)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6e20f7995304c27b8b041e69c372c87 | COC(=O)c1ccc(B(O)O)cc1.COc1ccc(Br)nc1>>COC(=O)c1ccc(-c2ccc(OC)cn2)cc1 | COC(=O)C1=CC=C(C=C1)B(O)O.BrC1=NC=C(C=C1)OC>>COC=1C=CC(=NC1)C1=CC=C(C(=O)OC)C=C1 | OB(O)[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][cH:17]1.Br[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][n:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][n:16]2)[cH:17][cH:18]1 | COC(=O)c1ccc(B(O)O)cc1.COc1ccc(Br)nc1 | COC(=O)c1ccc(-c2ccc(OC)cn2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | Repeating the operations of Production Example 14 using 4-(methoxycarbonyl)phenylboronic acid and 2-bromo-5-methoxypyridine, methyl 4-(5-methoxy-2-pyridyl)benzoate was obtained. Hydrolyzing the same with 5N aqueous sodium hydroxide solution, the title compound was obtained as white solid.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | null | null | null | COC(=O)c1ccc(B(O)O)cc1.COc1ccc(Br)nc1>>COC(=O)c1ccc(-c2ccc(OC)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-813bc511fa8c488fbc2de6d165096ca0 | FC(F)c1ccc(Br)cn1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(-c2ccc(C(F)F)nc2)cc1 | C(=O)(O)C1=CC=C(C=C1)B(O)O.BrC=1C=CC(=NC1)C(F)F>>FC(C1=CC=C(C=N1)C1=CC=C(C=C1)C(=O)O)F | Br[c:8]1[cH:9][cH:10][c:11]([CH:12]([F:13])[F:14])[n:15][cH:16]1.OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:18][cH:17]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([CH:12]([F:13])[F:14])[n:15][cH:16]2)[cH:17][cH:18]1 | FC(F)c1ccc(Br)cn1.O=C(O)c1ccc(B(O)O)cc1 | O=C(O)c1ccc(-c2ccc(C(F)F)nc2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1):[c:10]:[c:11] | null | [] | null | null | null | null | Operations similar to those of Production Example 14 were conducted using 4-carboxyphenylboronic acid and 5-bromo-2-(difluoromethyl)pyridine, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | null | null | null | FC(F)c1ccc(Br)cn1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(-c2ccc(C(F)F)nc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b62752ee596f4f8c86b7587014a8b2bd | FC(F)Oc1ccc(Br)nc1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(-c2ccc(OC(F)F)cn2)cc1 | C(=O)(O)C1=CC=C(C=C1)B(O)O.BrC1=NC=C(C=C1)OC(F)F>>FC(OC=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O)F | Br[c:8]1[cH:9][cH:10][c:11]([O:12][CH:13]([F:14])[F:15])[cH:16][n:17]1.OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:19][cH:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH:13]([F:14])[F:15])[cH:16][n:17]2)[cH:18][cH:19]1 | FC(F)Oc1ccc(Br)nc1.O=C(O)c1ccc(B(O)O)cc1 | O=C(O)c1ccc(-c2ccc(OC(F)F)cn2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | Operations similar to those of Production Example 14 were conducted using 4-carboxyphenylboronic acid and 2-bromo-5-(difluoromethoxy)pyridine, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | null | null | null | FC(F)Oc1ccc(Br)nc1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(-c2ccc(OC(F)F)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d32d41c62af2483c8f0d709efb1581f4 | O=C(O)c1ccc(Cl)nc1.OB(O)c1ccc(F)cc1>>O=C(O)c1ccc(-c2ccc(F)cc2)nc1 | ClC1=NC=C(C(=O)O)C=C1.FC1=CC=C(C=C1)B(O)O>>FC1=CC=C(C=C1)C1=NC=C(C(=O)O)C=C1 | Cl[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:16][n:15]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15][cH:16]1 | O=C(O)c1ccc(Cl)nc1.OB(O)c1ccc(F)cc1 | O=C(O)c1ccc(-c2ccc(F)cc2)nc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | Operations similar to those of Production Example 14 were conducted using 6-chloronicotinic acid and 4-fluorophenylboronic acid, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HCl.B | null | null | null | O=C(O)c1ccc(Cl)nc1.OB(O)c1ccc(F)cc1>>O=C(O)c1ccc(-c2ccc(F)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb7c899b325548aa861fe8f1f8dc9983 | O=C(O)c1ccc(Br)cn1.OB(O)c1ccc(F)cc1>>O=C(O)c1ccc(-c2ccc(F)cc2)cn1 | BrC=1C=CC(=NC1)C(=O)O.FC1=CC=C(C=C1)B(O)O>>FC1=CC=C(C=C1)C=1C=CC(=NC1)C(=O)O | Br[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[n:16][cH:15]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:15][n:16]1 | O=C(O)c1ccc(Br)cn1.OB(O)c1ccc(F)cc1 | O=C(O)c1ccc(-c2ccc(F)cc2)cn1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:9]:[c:8]:1 | null | [] | null | null | null | null | Operations similar to those of Production Example 14 were conducted using 5-bromo-2-pyridinecarboxylic acid and 4-fluorophenylboronic acid, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.B | null | null | null | O=C(O)c1ccc(Br)cn1.OB(O)c1ccc(F)cc1>>O=C(O)c1ccc(-c2ccc(F)cc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4c9e6e11d9449da9308875330f71e1e | Nc1cnc(Br)cn1.OB(O)c1ccc(F)cc1>>Nc1cnc(-c2ccc(F)cc2)cn1 | NC1=NC=C(N=C1)Br.FC1=CC=C(C=C1)B(O)O>>NC1=NC=C(N=C1)C1=CC=C(C=C1)F | Br[c:5]1[n:4][cH:3][c:2]([NH2:1])[n:14][cH:13]1.OB(O)[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[NH2:1][c:2]1[cH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[cH:13][n:14]1 | Nc1cnc(Br)cn1.OB(O)c1ccc(F)cc1 | Nc1cnc(-c2ccc(F)cc2)cn1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | f4f2599a1f2d23f122d9e68430d5dc3c8a9f800f7adcc4136d8b17b1c1c7d091 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cnccn2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10]:[c:11] | null | [] | null | null | null | null | Conducting the operations similar to those of Production Example 14 using 2-amino-5-bromopyrazine (2.7 g) and 4-fluorophenylboronic acid (3.4 g), 2-amino-5-(4-fluorophenyl)pyrazine was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cnccn1.c1ccccc1 | c1cnccn1.c1ccccc1 | c1cnccn1.c1ccccc1 | HBr.B | null | null | null | Nc1cnc(Br)cn1.OB(O)c1ccc(F)cc1>>Nc1cnc(-c2ccc(F)cc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5a303d6deb74c0b93190cb64720a986 | O=C(O)c1ncc(Br)cn1.OB(O)c1ccccc1>>O=C(O)c1ncc(-c2ccccc2)cn1 | BrC=1C=NC(=NC1)C(=O)O.C1(=CC=CC=C1)B(O)O>>C1(=CC=CC=C1)C=1C=NC(=NC1)C(=O)O | Br[c:7]1[cH:6][n:5][c:4]([C:2](=[O:1])[OH:3])[n:15][cH:14]1.OB(O)[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][n:15]1 | O=C(O)c1ncc(Br)cn1.OB(O)c1ccccc1 | O=C(O)c1ncc(-c2ccccc2)cn1 | null | null | null | C-C Coupling | Suzuki | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cncnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[#7;a:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:9]:[#7;a:8]:1 | null | [] | null | null | null | null | Conducting the operations similar to those of Production Example 14 using 5-bromopyrimidine-2-carboxylic acid and phenylboronic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr.B | null | null | null | O=C(O)c1ncc(Br)cn1.OB(O)c1ccccc1>>O=C(O)c1ncc(-c2ccccc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b274ef78305f4bec9deccbe1812eac39 | O=C(O)c1ncc(Br)cn1.OB(O)c1ccc(F)cc1>>O=C(O)c1ncc(-c2ccc(F)cc2)cn1 | BrC=1C=NC(=NC1)C(=O)O.FC1=CC=C(C=C1)B(O)O>>FC1=CC=C(C=C1)C=1C=NC(=NC1)C(=O)O | Br[c:7]1[cH:6][n:5][c:4]([C:2](=[O:1])[OH:3])[n:16][cH:15]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:15][n:16]1 | O=C(O)c1ncc(Br)cn1.OB(O)c1ccc(F)cc1 | O=C(O)c1ncc(-c2ccc(F)cc2)cn1 | null | null | null | C-C Coupling | Suzuki | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cncnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[#7;a:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:9]:[#7;a:8]:1 | null | [] | null | null | null | null | Conducting the operations similar to those of Production Example 14 using 5-bromopyrimidine-2-carboxylic acid and 4-fluorophenylboronic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr.B | null | null | null | O=C(O)c1ncc(Br)cn1.OB(O)c1ccc(F)cc1>>O=C(O)c1ncc(-c2ccc(F)cc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f119b61d4c9409ea3a8cfb2e1e3c18d | O=C(O)c1ncc(Br)cn1.OB(O)c1ccc(F)nc1>>O=C(O)c1ncc(-c2ccc(F)nc2)cn1 | BrC=1C=NC(=NC1)C(=O)O.FC1=CC=C(C=N1)B(O)O>>FC1=CC=C(C=N1)C=1C=NC(=NC1)C(=O)O | Br[c:7]1[cH:6][n:5][c:4]([C:2](=[O:1])[OH:3])[n:16][cH:15]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([F:12])[n:13][cH:14]1>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[n:13][cH:14]2)[cH:15][n:16]1 | O=C(O)c1ncc(Br)cn1.OB(O)c1ccc(F)nc1 | O=C(O)c1ncc(-c2ccc(F)nc2)cn1 | null | null | null | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[#7;a:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:2):[c:9]:[#7;a:8]:1 | null | [] | null | null | null | null | Conducting the operations similar to those of Production Example 14 using 5-bromopyrimidine-2-carboxylic acid and 6-fluoro-3-pyridineboronic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | null | null | null | O=C(O)c1ncc(Br)cn1.OB(O)c1ccc(F)nc1>>O=C(O)c1ncc(-c2ccc(F)nc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77e5cd59cb334e53be89678974c2cb6b | CC(C)c1cn2cc([N+](=O)[O-])ccc2n1>>CC(C)c1cn2cc(N)ccc2n1 | [H][H].Br.C(C)(C)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1>>Br.NC=1C=CC=2N(C1)C=C(N2)C(C)C | O=[N+:10]([O-])[c:9]1[cH:8][n:7]2[cH:6][c:5]([CH:3]([CH3:2])[CH3:4])[n:14][c:13]2[cH:12][cH:11]1>>[CH3:2][CH:3]([CH3:4])[c:5]1[cH:6][n:7]2[cH:8][c:9]([NH2:10])[cH:11][cH:12][c:13]2[n:14]1 | CC(C)c1cn2cc([N+](=O)[O-])ccc2n1 | CC(C)c1cn2cc(N)ccc2n1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccn2ccnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 99.7 | [{"value": 99.7, "product": "Br.NC=1C=CC=2N(C1)C=C(N2)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a methanol solution (20 ml) containing 2-isopropyl-6-nitroimidazo[1,2-a]pyridine hydrobromide (280 mg), 10% palladium-on-carbon (30 mg) was added, and inside the reaction system was substituted with hydrogen, followed by an hour's stirring at room temperature. The reaction liquid was filtered through Celite™. Concen... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccn2ccnc2c1 | Other | [Pd].CO | null | null | CC(C)c1cn2cc([N+](=O)[O-])ccc2n1>[Pd].CO>CC(C)c1cn2cc(N)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d377743f8c224d618db6e7cc8d9e42ca | CC(C)c1cn2cc([N+](=O)[O-])ccc2n1.O=C(O)c1ccc(-c2ccc(F)cc2)cc1>>CC(C)c1cn2cc(NC(=O)c3ccc(-c4ccc(F)cc4)cc3)ccc2n1 | Br.C(C)(C)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1.FC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O>>FC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)NC=1C=CC=2N(C1)C=C(N2)C(C)C | O=[N+:9]([O-])[c:8]1[cH:7][n:6]2[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:28][c:27]2[cH:26][cH:25]1.O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[cH:23][cH:24]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][n:6]2[cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]3[cH:13][cH:14][c:15](-[c:16]4[c... | CC(C)c1cn2cc([N+](=O)[O-])ccc2n1.O=C(O)c1ccc(-c2ccc(F)cc2)cc1 | CC(C)c1cn2cc(NC(=O)c3ccc(-c4ccc(F)cc4)cc3)ccc2n1 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nccn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-isopropyl-6-nitroimidazo[1,2-a]pyridine hydrobromide and 4′-fluoro[1,1′-biphenyl]-4-carboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)c1cn2cc([N+](=O)[O-])ccc2n1.O=C(O)c1ccc(-c2ccc(F)cc2)cc1>>CC(C)c1cn2cc(NC(=O)c3ccc(-c4ccc(F)cc4)cc3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a69300b5d7a74e068179e9b4bf9f57aa | Cc1nc2ccc([N+](=O)[O-])cn2c1C.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>Cc1nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn2c1C | CC=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F>>CC=1N=C2N(C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(F)(F)F)C1C | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:4]2[n:3][c:2]([CH3:1])[c:29]([CH3:30])[n:28]2[cH:27]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[cH:25][cH:26]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14](-[c:15]... | Cc1nc2ccc([N+](=O)[O-])cn2c1C.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | Cc1nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn2c1C | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nccn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2,3-dimethyl-6-nitroimidazo[1,2-a]pyridine and 4′-(trifluoromethyl)-[1,1′-biphenyl]-4-carboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | Cc1nc2ccc([N+](=O)[O-])cn2c1C.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>Cc1nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa58958213264d5881885ba6b7704af5 | Cc1cnc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>Cc1cnc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 | CC1=CN=C2N1C=C(C=C2)[N+](=O)[O-].FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F>>CC1=CN=C2N1C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(F)(F)F | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]2[n:4][cH:3][c:2]([CH3:1])[n:29]2[cH:28]1.O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]2)[cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]3[cH:13][cH:14][c:15](-[c:16]4[... | Cc1cnc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | Cc1cnc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nccn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 3-methyl-6-nitroimidazo[1,2-a]pyridine and 4′-(trifluoromethyl)-[1,1′-biphenyl]-4-carboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | Cc1cnc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>Cc1cnc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c23d63b115b4e2c8c297b0fec9a09d8 | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1.O=[N+]([O-])c1ccc2nc3c(n2c1)CCCC3>>O=C(Nc1ccc2nc3c(n2c1)CCCC3)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | [N+](=O)([O-])C=1C=CC2=NC3=C(N2C1)CCCC3.FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F>>C1=C(C=CC2=NC3=C(N21)CCCC3)NC(=O)C3=CC=C(C=C3)C3=CC=C(C=C3)C(F)(F)F | O[C:2](=[O:1])[c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]2)[cH:31][cH:32]1.O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]3[c:10]([n:11]2[cH:12]1)[CH2:13][CH2:14][CH2:15][CH2:16]3>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]3[c:10]([n:11]2[cH:12]1)[CH2:... | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1.O=[N+]([O-])c1ccc2nc3c(n2c1)CCCC3 | O=C(Nc1ccc2nc3c(n2c1)CCCC3)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc3c(n2c1)CCCC3)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-nitro-6,7,8,9-tetrahydropyrido[1,2-a]benzimidazole and 4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2c3c(nc2c1)CCCC3.c1ccccc1.c1ccccc1 | Other | null | null | null | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1.O=[N+]([O-])c1ccc2nc3c(n2c1)CCCC3>>O=C(Nc1ccc2nc3c(n2c1)CCCC3)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67a716d4480145e18f502b905ad0f4c3 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(F)(F)F)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:32]2[cH:31]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]2)[cH:29][cH:30]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12]... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under re... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42e9fc4380bc4881991ed9fcabf600a7 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cn4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(C=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O)(F)F.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C2=NC=C(C=C2)C(F)(F)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:32]2[cH:31]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][n:28]2)[cH:29][cH:30]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cn2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cn4)cc3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-[5-(trifluoromethyl)-2-pyridyl]benzenecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cn2)cc1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cn4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-471546c6ac364d7c96d3d1386dc55f67 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)nc2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)nc4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(C1=CC=C(C=N1)C1=CC=C(C=C1)C(=O)O)(F)F.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C=2C=NC(=CC2)C(F)(F)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:32]2[cH:31]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[n:27][cH:28]2)[cH:29][cH:30]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)nc2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)nc4)cc3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2cccnc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-[6-(trifluoromethyl)-3-pyridyl]benzenecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)nc2)cc1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)nc4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-faeec0217aca4bbd90470800dbe0ea2c | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)nc2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)nc4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC1=CC=C(C=N1)C1=CC=C(C=C1)C(=O)O.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C=2C=NC(=CC2)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([F:23])[n:24][cH:25]2)[cH:26][cH:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)nc2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)nc4)cc3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2cccnc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-(6-fluoro-3-pyridyl)benzenecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)nc2)cc1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)nc4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddfe61d417f14693b2cea5cbaec64845 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(Cl)cn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(Cl)cn4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.ClC=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O>>ClC=1C=CC(=NC1)C1=CC=C(C(=O)NC=2C=CC=3N(C2)C(=C(N3)C3CC3)C)C=C1 | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][n:25]2)[cH:26][cH:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(Cl)cn2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(Cl)cn4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-(5-chloro-2-pyridyl)benzenecarboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(Cl)cn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(Cl)cn4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64c476b744b54932a8fec493085dd830 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ncc(-c2ccc(F)cc2)cn1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ncc(-c4ccc(F)cc4)cn3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC1=CC=C(C=C1)C=1C=NC(=NC1)C(=O)O.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=NC=C(C=N2)C2=CC=C(C=C2)F)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[n:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[cH:26][n:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[n... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ncc(-c2ccc(F)cc2)cn1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ncc(-c4ccc(F)cc4)cn3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ncc(-c2ccccc2)cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7].O=[N+;H0;D3:8](-[O-])-[c:9](:[c:10]):[c:11]:[#7;a:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:1)-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 5-(4-fluorophenyl)-2-pyrimidinecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under reduced pressure. The title compound was obtained as white solid.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1cncnc1.c1ccccc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ncc(-c2ccc(F)cc2)cn1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ncc(-c4ccc(F)cc4)cn3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7fa36e4a61548c682686ce652ecc4d0 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ncc(-c2cccc(F)c2)cn1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ncc(-c4cccc(F)c4)cn3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC=1C=C(C=CC1)C=1C=NC(=NC1)C(=O)O.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=NC=C(C=N2)C2=CC(=CC=C2)F)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[n:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]2)[cH:26][n:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[n... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ncc(-c2cccc(F)c2)cn1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ncc(-c4cccc(F)c4)cn3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ncc(-c2ccccc2)cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7].O=[N+;H0;D3:8](-[O-])-[c:9](:[c:10]):[c:11]:[#7;a:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:1)-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 5-(3-fluorophenyl)-2-pyrimidinecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1cncnc1.c1ccccc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ncc(-c2cccc(F)c2)cn1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ncc(-c4cccc(F)c4)cn3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5893d9713992467291546c5e764751aa | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1cnc(-c2ccc(F)cc2)cn1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3cnc(-c4ccc(F)cc4)cn3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC1=CC=C(C=C1)C=1N=CC(=NC1)C(=O)O.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=NC=C(N=C2)C2=CC=C(C=C2)F)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[cH:16][n:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[cH:26][n:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[c... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1cnc(-c2ccc(F)cc2)cn1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3cnc(-c4ccc(F)cc4)cn3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1cnc(-c2ccccc2)cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.O=[N+;H0;D3:9](-[O-])-[c:10](:[c:11]):[c:12]:[#7;a:13]1:[c:14]:[c:15]:[#7;a:16]:[c:17]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]1:[c:14]:[c:15]:[#7;a:16]:[c:17]:1)-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1 | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 5-(4-fluorophenyl)-2-pyrazinecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1cnccn1.c1ccccc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1cnc(-c2ccc(F)cc2)cn1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3cnc(-c4ccc(F)cc4)cn3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ac85a5ef6bb47a99958880427975d44 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)cc2)cn1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)cc4)cn3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC1=CC=C(C=C1)C=1C=CC(=NC1)C(=O)O.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=NC=C(C=C2)C2=CC=C(C=C2)F)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[cH:26][n:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)cc2)cn1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)cc4)cn3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccc2)cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].O=[N+;H0;D3:7](-[O-])-[c:8](:[c:9]):[c:10]:[#7;a:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 5-(4-fluorophenyl)-2-pyridinecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccncc1.c1ccccc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)cc2)cn1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)cc4)cn3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3d8e3b51cb34b638d44b7ce49ebfd54 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)cc2)nc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)cc4)nc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC1=CC=C(C=C1)C1=NC=C(C(=O)O)C=C1.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CN=C(C=C2)C2=CC=C(C=C2)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[n:26][cH:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)cc2)nc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)cc4)nc3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccc2)nc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].O=[N+;H0;D3:8](-[O-])-[c:9](:[c:10]):[c:11]:[#7;a:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:1)-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 6-(4-fluorophenyl)nicotinic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate solution and concentration under reduced pressure. The t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccncc1.c1ccccc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(F)cc2)nc1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)cc4)nc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78f3a0969f734ff0bb0c3bcd6300676e | Cc1c(C2CCOC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cn2)cc1>>Cc1c(C2CCOC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cn4)cc3)cn12 | CC1=C(N=C2N1C=C(C=C2)[N+](=O)[O-])C2COCC2.FC(C=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O)(F)F>>CC1=C(N=C2N1C=C(C=C2)NC(C2=CC=C(C=C2)C2=NC=C(C=C2)C(F)(F)F)=O)C2COCC2 | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]2[n:9][c:3]([CH:4]3[CH2:5][CH2:6][O:7][CH2:8]3)[c:2]([CH3:1])[n:34]2[cH:33]1.O[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][n:30]2)[cH:31][cH:32]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6][O:7][CH2:8]2)[n:9][c:10]2[... | Cc1c(C2CCOC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cn2)cc1 | Cc1c(C2CCOC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cn4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CCOC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 3-methyl-6-nitro-2-tetrahydro-3-furanylimidazo[1,2-a]pyridine and 4-[5-(trifluoromethyl)-2-pyridyl]benzenecarboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CCOC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | null | null | null | Cc1c(C2CCOC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cn2)cc1>>Cc1c(C2CCOC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cn4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5705660825af490f91854d7019e6ba9d | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccccn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccccn4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.N1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)O.Cl.C(C)(=O)OCC>>Cl.C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C2=NC=CC=C2)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:28]2[cH:27]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[cH:25][cH:26]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[cH:16][... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccccn2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccccn4)cc3)cn12 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | The title compound was obtained as white solid by conducting the operations similar to those of Example 1, using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-(2-pyridyl)benzenecarboxylic acid. The resulting solid was dissolved in ethyl acetate, followed by addition of 4N hydrochloric acid-ethyl acetate so... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | C(C)(=O)OCC | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccccn2)cc1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccccn4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68a0db620496425fa19765d6d6a62c4a | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)CCc1ccc(C(F)(F)F)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)CCc3ccc(C(F)(F)F)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(C1=CC=C(C=C1)CCC(=O)O)(F)F>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(CCC2=CC=C(C=C2)C(F)(F)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:28]2[cH:27]1.O[C:13](=[O:14])[CH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][CH2:1... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)CCc1ccc(C(F)(F)F)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)CCc3ccc(C(F)(F)F)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(CCc1ccccc1)Nc1ccc2nc(C3CC3)cn2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]:[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:1 | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 3-[4-(trifluoromethyl)phenyl]propionic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)CCc1ccc(C(F)(F)F)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)CCc3ccc(C(F)(F)F)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d92e00a2dc54f048bb7884db64f9ae2 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)CCc1ccc(C(F)(F)F)nc1>>Cc1c(C2CC2)nc2ccc(NC(=O)CCc3ccc(C(F)(F)F)nc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(C1=CC=C(C=N1)CCC(=O)O)(F)F>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(CCC=2C=NC(=CC2)C(F)(F)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:28]2[cH:27]1.O[C:13](=[O:14])[CH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[n:25][cH:26]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][CH2:16... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)CCc1ccc(C(F)(F)F)nc1 | Cc1c(C2CC2)nc2ccc(NC(=O)CCc3ccc(C(F)(F)F)nc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(CCc1cccnc1)Nc1ccc2nc(C3CC3)cn2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]:[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:1 | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 3-[6-(trifluoromethyl)-3-pyridyl]propionic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccncc1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)CCc1ccc(C(F)(F)F)nc1>>Cc1c(C2CC2)nc2ccc(NC(=O)CCc3ccc(C(F)(F)F)nc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cee137feb6da4ccf9328aa7dec8e873c | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(OC(F)F)cn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(OC(F)F)cn4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(OC=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O)F>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C2=NC=C(C=C2)OC(F)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:32]2[cH:31]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([O:23][CH:24]([F:25])[F:26])[cH:27][n:28]2)[cH:29][cH:30]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(OC(F)F)cn2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(OC(F)F)cn4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-[5-(difluoromethoxy)-2-pyridyl]benzenecarboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(OC(F)F)cn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(OC(F)F)cn4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1e9d625d2be4c0bb5d8523a66c12da0 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)F)nc2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)F)nc4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC(C1=CC=C(C=N1)C1=CC=C(C=C1)C(=O)O)F>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C=2C=NC(=CC2)C(F)F)=O)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:31]2[cH:30]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([CH:23]([F:24])[F:25])[n:26][cH:27]2)[cH:28][cH:29]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)F)nc2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)F)nc4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2cccnc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-[6-(difluoromethyl)-3-pyridyl]benzenecarboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccncc1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)F)nc2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)F)nc4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b566a84903c24897bebab23fb36e3eff | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1F>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3F)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.FC=1C=C(C=CC1C(=O)O)C1=CC=C(C=C1)C(F)(F)F>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=C(C=C(C=C2)C2=CC=C(C=C2)C(F)(F)F)F)C1C | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:33]2[cH:32]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]2)[cH:29][c:30]1[F:31]>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([N... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1F | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3F)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 3-fluoro-4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1F>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3F)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b05bc350b84b43b582635aa0845d7bf0 | CS(=O)(=O)c1ccc(-c2ccc(C(=O)O)cc2)cc1.Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(S(C)(=O)=O)cc4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.CS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)S(=O)(=O)C)C1C | O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27][cH:28]2)[cH:29][cH:30]1.O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:32]2[cH:31]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH... | CS(=O)(=O)c1ccc(-c2ccc(C(=O)O)cc2)cc1.Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(S(C)(=O)=O)cc4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Conducting the operations similar to those of Example 1 using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4′-(methylsulfonyl)[1,1′-biphenyl]-4-carboxylic acid, the title compound was obtained as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | CS(=O)(=O)c1ccc(-c2ccc(C(=O)O)cc2)cc1.Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(S(C)(=O)=O)cc4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-535d476dad0143fa8e4b3d3235b1f036 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(Cl)nn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(Cl)nn4)cc3)cn12 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.ClC1=CC=C(N=N1)C1=CC=C(C=C1)C(=O)O>>ClC1=CC=C(N=N1)C1=CC=C(C(=O)NC=2C=CC=3N(C2)C(=C(N3)C3CC3)C)C=C1 | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:3]([CH:4]3[CH2:5][CH2:6]3)[c:2]([CH3:1])[n:29]2[cH:28]1.O[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([Cl:23])[n:24][n:25]2)[cH:26][cH:27]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]3[... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(Cl)nn2)cc1 | Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(Cl)nn4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2cccnn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-(6-chloro-3-pyridazinyl)benzenecarboxylic acid, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | C1CC1.c1ccn2ccnc2c1.c1ccccc1.c1ccnnc1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(Cl)nn2)cc1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(Cl)nn4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-617b41c59b904c528d3936db5b9d1ae4 | COc1ccc(-c2ccc(C(=O)O)cc2)nc1.Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12>>COc1ccc(-c2ccc(C(=O)Nc3ccc4nc(C5CC5)c(C)n4c3)cc2)nc1 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.COC=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C2=NC=C(C=C2)OC)=O)C1C | O[C:11]([c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][n:29]2)[cH:28][cH:27]1)=[O:12].O=[N+:13]([O-])[c:14]1[cH:15][cH:16][c:17]2[n:18][c:19]([CH:20]3[CH2:21][CH2:22]3)[c:23]([CH3:24])[n:25]2[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]3[cH:... | COc1ccc(-c2ccc(C(=O)O)cc2)nc1.Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12 | COc1ccc(-c2ccc(C(=O)Nc3ccc4nc(C5CC5)c(C)n4c3)cc2)nc1 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-(5-methoxy-2-pyridyl)benzenecarboxylic acid, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccncc1.c1ccccc1.c1ccn2ccnc2c1.C1CC1 | Other | null | null | null | COc1ccc(-c2ccc(C(=O)O)cc2)nc1.Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12>>COc1ccc(-c2ccc(C(=O)Nc3ccc4nc(C5CC5)c(C)n4c3)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-936628b1b56b4a2fa90f81010c84e676 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.Cc1ccc(-c2ccc(C(=O)O)cc2)nc1>>Cc1ccc(-c2ccc(C(=O)Nc3ccc4nc(C5CC5)c(C)n4c3)cc2)nc1 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C.CC=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(C2=CC=C(C=C2)C2=NC=C(C=C2)C)=O)C1C | O=[N+:12]([O-])[c:13]1[cH:14][cH:15][c:16]2[n:17][c:18]([CH:19]3[CH2:20][CH2:21]3)[c:22]([CH3:23])[n:24]2[cH:25]1.O[C:10]([c:9]1[cH:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:29][n:28]2)[cH:27][cH:26]1)=[O:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]3[cH:14][cH:15][c... | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.Cc1ccc(-c2ccc(C(=O)O)cc2)nc1 | Cc1ccc(-c2ccc(C(=O)Nc3ccc4nc(C5CC5)c(C)n4c3)cc2)nc1 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to Example 1 were conducted using 2-cyclopropyl-3-methyl-6-nitroimidazo[1,2-a]pyridine and 4-(5-methyl-2-pyridyl)benzenecarboxylic acid, to provide the title compound as white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccncc1.c1ccccc1.c1ccn2ccnc2c1.C1CC1 | Other | null | null | null | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.Cc1ccc(-c2ccc(C(=O)O)cc2)nc1>>Cc1ccc(-c2ccc(C(=O)Nc3ccc4nc(C5CC5)c(C)n4c3)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7374e82fce514343986cd10121234652 | CCOC(=O)c1cn2cc([N+](=O)[O-])ccc2n1.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>CCOC(=O)c1cn2cc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)ccc2n1 | [N+](=O)([O-])C=1C=CC=2N(C1)C=C(N2)C(=O)OCC.FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F>>FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)NC=1C=CC=2N(C1)C=C(N2)C(=O)OCC)(F)F | O=[N+:11]([O-])[c:10]1[cH:9][n:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:33][c:32]2[cH:31][cH:30]1.O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]2)[cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]2[cH:9][c:10]([NH:11][C:12](... | CCOC(=O)c1cn2cc([N+](=O)[O-])ccc2n1.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | CCOC(=O)c1cn2cc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)ccc2n1 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nccn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | 31.1 | [{"value": 31.1, "product": "FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)NC=1C=CC=2N(C1)C=C(N2)C(=O)OCC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Operations similar to Example 1 were conducted using ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate (600 mg) and 4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid (700 mg), to provide ethyl 6-({[4′-(trifluoromethyl)[1,1′-biphenyl]-4-yl]carbonyl}-amino)imidazo[1,2-a]pyridine-2-carboxylate (360 mg) as white solid.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCOC(=O)c1cn2cc([N+](=O)[O-])ccc2n1.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>CCOC(=O)c1cn2cc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35e34d64bc5c4d9e8fe81e0963413302 | COC(=O)c1nc2ccc([N+](=O)[O-])cn2c1C.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>COC(=O)c1nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn2c1C | CC1=C(N=C2N1C=C(C=C2)[N+](=O)[O-])C(=O)OC.FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F>>CC1=C(N=C2N1C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(F)(F)F)C(=O)OC | O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:7]2[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:32]([CH3:33])[n:31]2[cH:30]1.O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]2)[cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=... | COC(=O)c1nc2ccc([N+](=O)[O-])cn2c1C.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | COC(=O)c1nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn2c1C | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nccn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using methyl 3-methyl-6-nitroimidazo[1,2-a]pyridine-2-carboxylate and 4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid, to provide methyl 3-methyl-6-({[4′-(trifluoromethyl)[1,1′-biphenyl]-4-yl]-carbonyl}amino)-imidazo[1,2-a]pyridine-2-carboxylate as white sol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | COC(=O)c1nc2ccc([N+](=O)[O-])cn2c1C.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>COC(=O)c1nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c68a44aad67a41719d3f49522f7f6d59 | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1.O=[N+]([O-])c1ccc2nc(C3CC3)cn2c1>>O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | Br.C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1.FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F>>C1(CC1)C=1N=C2N(C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(F)(F)F)C1 | O[C:2](=[O:1])[c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]2)[cH:30][cH:31]1.O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12]3)[cH:13][n:14]2[cH:15]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12]3)[cH:13][n:... | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1.O=[N+]([O-])c1ccc2nc(C3CC3)cn2c1 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-6-nitroimidazo[1,2-a]pyridine hydrobromide and 4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid, to provide N-(2-cyclopropylimidazo[1,2-a]pyridin-6-yl)-4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxamide as white solid.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.C1CC1.c1ccccc1.c1ccccc1 | Other | null | null | null | O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1.O=[N+]([O-])c1ccc2nc(C3CC3)cn2c1>>O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fac5f2b041624d1c8c5de8b4c0b5b93e | O=C(O)c1ccc(-c2ccc(Cl)cn2)cc1.O=[N+]([O-])c1ccc2nc(C3CC3)cn2c1>>O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccc(Cl)cn2)cc1 | C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1.ClC=1C=CC(=NC1)C1=CC=C(C=C1)C(=O)O>>ClC=1C=CC(=NC1)C1=CC=C(C(=O)NC=2C=CC=3N(C2)C=C(N3)C3CC3)C=C1 | O[C:2](=[O:1])[c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]2)[cH:27][cH:28]1.O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12]3)[cH:13][n:14]2[cH:15]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12]3)[cH:13][n:14]2[cH:15]1)[c:16]1[c... | O=C(O)c1ccc(-c2ccc(Cl)cn2)cc1.O=[N+]([O-])c1ccc2nc(C3CC3)cn2c1 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccc(Cl)cn2)cc1 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Operations similar to those of Example 1 were conducted using 2-cyclopropyl-6-nitroimidazo[1,2-a]pyridine and 4-(5-chloro-2-pyridyl)benzenecarboxylic acid, to provide 4-(5-chloro-2-pyridyl)-N-(2-cyclopropylimidazo[1,2-a]pyridine-6-yl)benzamide as white solid. Further treating the resulting compound in the manner simila... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.C1CC1.c1ccccc1.c1ccncc1 | Other | null | null | null | O=C(O)c1ccc(-c2ccc(Cl)cn2)cc1.O=[N+]([O-])c1ccc2nc(C3CC3)cn2c1>>O=C(Nc1ccc2nc(C3CC3)cn2c1)c1ccc(-c2ccc(Cl)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f235ba78a7b243babcbba2117626aae8 | Cc1c(N(C)C(=O)C(F)(F)F)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>Cc1c(N(C)C(=O)C(F)(F)F)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 | FC(C(=O)N(C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C)C)(F)F.FC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)(F)F>>CC1=C(N=C2N1C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(F)(F)F)N(C(C(F)(F)F)=O)C | O=[N+:17]([O-])[c:16]1[cH:15][cH:14][c:13]2[n:12][c:3]([N:4]([CH3:5])[C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[c:2]([CH3:1])[n:37]2[cH:36]1.O[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23](-[c:24]2[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]2)[cH:34][cH:35]1>>[CH3:1][c:2]1[c:3]([N:4]([CH3:5])[C:6](=[O:7])... | Cc1c(N(C)C(=O)C(F)(F)F)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | Cc1c(N(C)C(=O)C(F)(F)F)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 | null | null | null | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Nc1ccc2nccn2c1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[c:3](:[c:4]):[c:5] | 61.2 | [{"value": 61.2, "product": "CC1=C(N=C2N1C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(F)(F)F)N(C(C(F)(F)F)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Operations similar to Example 1 were conducted using 2,2,2-trifluoro-N-methyl-N-(3-methyl-6-nitroimidazo[1,2-a]pyridin-2-yl)acetamide (580 mg) and 4′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid (510 mg), to provide N-{3-methyl-2-[methyl(2,2,2-trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl}-4′(trifluoromethyl)-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | Other | null | null | null | Cc1c(N(C)C(=O)C(F)(F)F)nc2ccc([N+](=O)[O-])cn12.O=C(O)c1ccc(-c2ccc(C(F)(F)F)cc2)cc1>>Cc1c(N(C)C(=O)C(F)(F)F)nc2ccc(NC(=O)c3ccc(-c4ccc(C(F)(F)F)cc4)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-367f9957fbe3451b925fcad46fbcfe08 | CC1(C)OCC(CO)O1.CCCCCCCCCCCCCCCCBr>>CCCCCCCCCCCCCCCCOCC(O)CO | [OH-].[K+].C(CCCCCCCCCCCCCCC)Br.CC1(OCC(O1)CO)C>>C(CCCCCCCCCCCCCCC)OCC(O)CO | CC1(C)[O:17][CH2:18][CH:19]([CH2:21][OH:22])[O:20]1.Br[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH:19]([OH:... | CC1(C)OCC(CO)O1.CCCCCCCCCCCCCCCCBr | CCCCCCCCCCCCCCCCOCC(O)CO | null | null | C1=CC=CC=C1.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 52d9a9d601c7b22ee50eec30dd99222029787a08b6512bd1185a59a4beaa83df | 7c129380d3b6717e6dab4e7b3072bb9c9efc6e13cceeaeae34b29769460ca1a3 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C1(-C)-[O;H0;D2;+0:4]-[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[C:5]-[C:6](-[C:7])-[OH;D1;+0:8] | 77.2 | [{"value": 77.2, "product": "C(CCCCCCCCCCCCCCC)OCC(O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | D-Acetone glycerol (4 grams) for synthesis of L-ALLE or L-Acetone glycerol for synthesis of D-ALLE, powdered potassium hydroxide (approximately 10 grams) and hexadecyl bromide (9.3 grams) in benzene (100 ml) were stirred and refluxed for 5 hours, while removing the water formed by azeotropic distillation (compare W. J.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether | Ether.Secondary alcohol | C1COCO1 | null | null | HBr | C1=CC=CC=C1.CCOCC | null | null | CC1(C)OCC(CO)O1.CCCCCCCCCCCCCCCCBr>C1=CC=CC=C1.CCOCC>CCCCCCCCCCCCCCCCOCC(O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d290d528d94d46f3887291aa8600b3e6 | O=[N+]([O-])c1ccc(F)cc1>>O=[N+]([O-])c1ccccc1 | [N+](=O)([O-])C1=CC=C(C=C1)F.C(=O)(O)COC1=C(C=CC=C1)O.[O-]CCCC.[K+]>>[N+](=O)([O-])C1=CC=CC=C1 | F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:9][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | O=[N+]([O-])c1ccc(F)cc1 | O=[N+]([O-])c1ccccc1 | null | null | CC(=O)N(C)C | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5] | null | [] | null | null | null | null | 4-nitro-fluorobenzene and 2-(carboxymethoxy)phenol were reacted together in DMA in the presence of potassium butoxide for 2 hours at 150° C. to yield 4-(2-carboxymethoxy)-phenoxy)nitrobenzene.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CC(=O)N(C)C | null | null | O=[N+]([O-])c1ccc(F)cc1>CC(=O)N(C)C>O=[N+]([O-])c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bad3801cbdd44d1e820687480b1b160f | O=C(O)COc1ccccc1O.O=[N+]([O-])c1ccc(F)cc1>>O=C(O)COc1ccccc1Oc1ccc([N+](=O)[O-])cc1 | [N+](=O)([O-])C1=CC=C(C=C1)F.C(=O)(O)COC1=C(C=CC=C1)O.[O-]CCCC.[K+]>>C(=O)(O)COC1=C(OC2=CC=C(C=C2)[N+](=O)[O-])C=CC=C1 | [O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12].F[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[O:12][c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1 | O=C(O)COc1ccccc1O.O=[N+]([O-])c1ccc(F)cc1 | O=C(O)COc1ccccc1Oc1ccc([N+](=O)[O-])cc1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | null | null | null | null | 4-nitro-fluorobenzene and 2-(carboxymethoxy)phenol were reacted together in DMA in the presence of potassium butoxide for 2 hours at 150° C. to yield 4-(2-carboxymethoxy-phenoxy)nitrobenzene, intermediate 1.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CC(=O)N(C)C | null | null | O=C(O)COc1ccccc1O.O=[N+]([O-])c1ccc(F)cc1>CC(=O)N(C)C>O=C(O)COc1ccccc1Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e820eadf4754ff9a253078911dc2753 | COc1ccc2c(c1)C=CCN2>>COc1ccc2ncccc2c1 | COC=1C=C2C=CCNC2=CC1.P(=O)(Cl)(Cl)Cl>>COC=1C=C2C=CC=NC2=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:11]([cH:12]1)[CH:10]=[CH:9][CH2:8][NH:7]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1 | COc1ccc2c(c1)C=CCN2 | COc1ccc2ncccc2c1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 7ffe3cebf575efbc523acf75ea06ed0a5206dc9a6b0e18ee1d47ba78967e3a74 | 949c4079d4cfdc9fe16404f504e221120066c0603ac761a9f7931fdd0e4dbc8b | c1ccc2ncccc2c1 | [c:1]:[c:2]1:[c:3](:[c:4])-[NH;D2;+0:5]-[CH2;D2;+0:6]-[CH;D2;+0:7]=[CH;D2;+0:8]-1>>[c:1]:[c:2]1:[cH;D2;+0:8]:[cH;D2;+0:7]:[cH;D2;+0:6]:[n;H0;D2;+0:5]:[c:3]:1:[c:4] | 97 | [{"value": 97.0, "product": "COC=1C=C2C=CC=NC2=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-cyano, 4-oxo, 6-methoxy dihydroquinoline was reacted with phosphorus oxychloride in acetonitrile at 85° C. for 5 hr to give 3-cyano, 4-chloro, 6-methoxy quinoline 97% purity by HPLC
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | null | C1=Cc2ccccc2NC1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | C(C)#N | null | null | COc1ccc2c(c1)C=CCN2>C(C)#N>COc1ccc2ncccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e59939bc5984fb29736b4935ff5f651 | O=C(O)COc1ccccc1O.O=[N+]([O-])c1ccc(F)cc1>>O=C(O)COc1ccccc1Oc1ccc([N+](=O)[O-])cc1 | FC1=CC=C(C=C1)[N+](=O)[O-].OC1=C(OCC(=O)O)C=CC=C1.CC(C)([O-])C.[K+].CC(=O)N(C)C>>[N+](=O)([O-])C1=CC=C(OC2=C(OCC(=O)O)C=CC=C2)C=C1 | [O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12].F[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[O:12][c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1 | O=C(O)COc1ccccc1O.O=[N+]([O-])c1ccc(F)cc1 | O=C(O)COc1ccccc1Oc1ccc([N+](=O)[O-])cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | null | null | null | null | 4-(fluoro)nitrobenzene was reacted with 2-(2-hydroxyphenoxy)acetic acid in the presence of potassium t-butoxide/DMA at 150° C. for 2 hrs to give 2-[(2-(4-nitrophenoxy)phenoxy] acetic acid. The product was purified by chromatography.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | null | null | null | O=C(O)COc1ccccc1O.O=[N+]([O-])c1ccc(F)cc1>>O=C(O)COc1ccccc1Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e378f173bb444b7aee359cc610c6e24 | COc1ccnc(Cl)c1.Nc1ccc(O)cc1>>COc1ccnc(Oc2ccc(N)cc2)c1 | NC1=CC=C(C=C1)O.COC1=CC(=NC=C1)Cl.CC(C)(C)[O-].[K+]>>NC1=CC=C(OC2=NC=CC(=C2)OC)C=C1 | Cl[c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16]1.[OH:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]2)[cH:16]1 | COc1ccnc(Cl)c1.Nc1ccc(O)cc1 | COc1ccnc(Oc2ccc(N)cc2)c1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | null | null | null | null | 4-Aminophenol was reacted with 4-methoxy-2-chloropyridine in the presence of KOtBu/8-Crown-6/DMA at 150° C. for 5 hrs to give 2-(4-aminophenoxy)-4-methoxypyridine. The product was purified by chromatography.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | CC(=O)N(C)C | null | null | COc1ccnc(Cl)c1.Nc1ccc(O)cc1>CC(=O)N(C)C>COc1ccnc(Oc2ccc(N)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3d3340515b549119f073eff5ec74b45 | Nc1ccc(C(=O)O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1>>O=C(O)c1ccc2[nH]c(-c3ccc(Oc4ccccc4)cc3)nc2c1 | FC1=CC=C(OC2=CC=C(C=O)C=C2)C=C1.NC=1C=C(C(=O)O)C=CC1N.NC=1C=C(C(=O)N)C=CC1N>>O(C1=CC=CC=C1)C1=CC=C(C=C1)C1=NC2=C(N1)C=CC(=C2)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:24]([NH2:23])[cH:25]1.O=[CH:9][c:10]1[cH:11][cH:12][c:13]([O:14][c:15]2[cH:16][cH:17][c:18](F)[cH:19][cH:20]2)[cH:21][cH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([O:14][c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[cH:2... | Nc1ccc(C(=O)O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1 | O=C(O)c1ccc2[nH]c(-c3ccc(Oc4ccccc4)cc3)nc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f4ad6a1d90ab5bd0bba8c0e178876500d65d3160b8ab7cc88185242ee3258127 | 92b3cf8c078f72830f19960a989555674686a3e49e4dfd835e29457519e1be13 | c1ccc(Oc2ccc(-c3nc4ccccc4[nH]3)cc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=[CH;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:6]1:[n;H0;D2;+0:12]:[c:13](:[c:14]):[c:15](:[c:17]):[nH;D2;+0:16]:1):[c:10]:[c:11].[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c... | null | [] | null | null | null | null | This compound was prepared according to the methods described in Example 22 and Scheme 3, substituting 4-phenoxybenzaldehyde for 4-(4-fluoro-phenoxy)-benzaldehyde, and 3,4-diaminobenzoic acid for 3,4-diaminobenzoic acid amide.
Conditions: See reaction.notes.procedure_details.
Workup: This compound was prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Primary amine.Primary amine | null | c1ccccc1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1 | HF | null | null | null | Nc1ccc(C(=O)O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1>>O=C(O)c1ccc2[nH]c(-c3ccc(Oc4ccccc4)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc1638d34b704af28d1bf1ec97a8d690 | Nc1ccc(S(N)(=O)=O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1>>NS(=O)(=O)c1ccc2[nH]c(-c3ccc(Oc4ccccc4)cc3)nc2c1 | FC1=CC=C(OC2=CC=C(C=O)C=C2)C=C1.NC=1C=C(C=CC1N)S(=O)(=O)N.NC=1C=C(C(=O)N)C=CC1N>>O(C1=CC=CC=C1)C1=CC=C(C=C1)C1=NC2=C(N1)C=CC(=C2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:25]([NH2:24])[cH:26]1.O=[CH:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19](F)[cH:20][cH:21]2)[cH:22][cH:23]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[nH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][c:16]4[cH:17][cH:18][cH:19][... | Nc1ccc(S(N)(=O)=O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1 | NS(=O)(=O)c1ccc2[nH]c(-c3ccc(Oc4ccccc4)cc3)nc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f4ad6a1d90ab5bd0bba8c0e178876500d65d3160b8ab7cc88185242ee3258127 | 92b3cf8c078f72830f19960a989555674686a3e49e4dfd835e29457519e1be13 | c1ccc(Oc2ccc(-c3nc4ccccc4[nH]3)cc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=[CH;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:6]1:[n;H0;D2;+0:12]:[c:13](:[c:14]):[c:15](:[c:17]):[nH;D2;+0:16]:1):[c:10]:[c:11].[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c... | null | [] | null | null | null | null | This compound was prepared according to the methods described in Example 22 and Scheme 3, substituting 4-phenoxybenzaldehyde for 4-(4-fluoro-phenoxy)-benzaldehyde, and 3,4-diaminobenzene sulfonamide for 3,4-diaminobenzoic acid amide.
Conditions: See reaction.notes.procedure_details.
Workup: This compound was prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Primary amine.Primary amine | null | c1ccccc1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1 | HF | null | null | null | Nc1ccc(S(N)(=O)=O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1>>NS(=O)(=O)c1ccc2[nH]c(-c3ccc(Oc4ccccc4)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5acdadaf666d404ca4234f7ce496ba9b | Nc1ccc(C=O)cc1.O=S(=O)(Cl)c1ccc(Cl)c(Cl)c1>>O=Cc1ccc(NS(=O)(=O)c2ccc(Cl)c(Cl)c2)cc1 | NC1=CC=C(C=O)C=C1.N1=CC=CC=C1.ClC=1C=C(C=CC1Cl)S(=O)(=O)Cl.[N+](=O)([O-])C=1C=C(C=CC1)C1=NC2=C(N1)C=CC(=C2)C(=O)N>>ClC=1C=C(C=CC1Cl)S(=O)(=O)NC1=CC=C(C=C1)C=O | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:19][cH:20]1.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]2)[cH:19][cH:20]1 | Nc1ccc(C=O)cc1.O=S(=O)(Cl)c1ccc(Cl)c(Cl)c1 | O=Cc1ccc(NS(=O)(=O)c2ccc(Cl)c(Cl)c2)cc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 72 | [{"value": 72.0, "product": "ClC=1C=C(C=CC1Cl)S(=O)(=O)NC1=CC=C(C=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 2-(3-Nitro-phenyl)-1H-benzoimidazole-5-carboxylic acid amide. To a flask containing crude 4-amino-benzaldehyde (100 mg, 0.82 mmol), pyridine (0.15 mL, 1.87 mmol) and CH2Cl2 (4 mL), was added 3,4-dichlorobenzenesulfonyl chloride (184 mg, 0.75 mmol). The mixture was stirred for 16 h at room temperature, and was then cool... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 16 | Nc1ccc(C=O)cc1.O=S(=O)(Cl)c1ccc(Cl)c(Cl)c1>C(Cl)Cl>O=Cc1ccc(NS(=O)(=O)c2ccc(Cl)c(Cl)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1191f8a6159b4c1689edac52db4be715 | COc1ccc([N+](=O)[O-])c(N)n1.Nc1nc(Br)ccc1[N+](=O)[O-]>>Br.Nc1nc(O)ccc1[N+](=O)[O-] | BrC1=CC=C(C(=N1)N)[N+](=O)[O-].COC1=CC=C(C(=N1)N)[N+](=O)[O-]>>Br.NC1=C(C=CC(=N1)O)[N+](=O)[O-] | C[O:6][c:5]1[n:4][c:3]([NH2:2])[c:9]([N+:10](=[O:11])[O-:12])[cH:8][cH:7]1.Nc1nc([Br:1])ccc1[N+](=O)[O-]>>[BrH:1].[NH2:2][c:3]1[n:4][c:5]([OH:6])[cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12] | COc1ccc([N+](=O)[O-])c(N)n1.Nc1nc(Br)ccc1[N+](=O)[O-] | Br.Nc1nc(O)ccc1[N+](=O)[O-] | null | null | Br.C(C)(=O)O | Miscellaneous | OtherReaction | fd244eb0624fa384b510733d5e039f55f706479d2f18b9df581e8f92d9bb1fa0 | 3121ad2041919c6e76386d177bdfc4d5d056f74749761519904b3ec281c20584 | c1ccncc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].N-c1:n:c(-[Br;H0;D1;+0:6]):c:c:c:1-[N+](=O)-[O-]>>[BrH;D0;+0:6].[OH;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 95 | [{"value": 95.0, "product": "Br.NC1=C(C=CC(=N1)O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 6-Bromo-3-nitro-pyridin-2-ylamine. To a glass pressure vessel containing 6-methoxy-3-nitro-pyridin-2-ylamine (5.0 g, 29.5 mmol) was added 30% hydrogen bromide/acetic acid (60 mL). The vessel was sealed, and the contents were heated to 60° C. for 24 h. The reaction mixture was cooled, and the solvent was removed in vacu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Nitro group.Primary amine | Aromatic alcohol | c1ccncc1 | null | c1ccncc1 | HO- | Br.C(C)(=O)O | 60 | null | COc1ccc([N+](=O)[O-])c(N)n1.Nc1nc(Br)ccc1[N+](=O)[O-]>Br.C(C)(=O)O>Br.Nc1nc(O)ccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c6e0c3e1bcd45b8adc124b33ba845ca | N#Cc1ccc([N+](=O)[O-])c(N)n1>>N#Cc1ccc(N)c(N)n1 | ClC=1C=C(OC2=CC=C(C=C2)C=2NC=3C(=NC(=CC3)C(=O)N)N2)C=CC1Cl.NC1=C(C=CC(=N1)C#N)[N+](=O)[O-]>>NC=1C=CC(=NC1N)C#N | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[n:10][c:8]1[NH2:9]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([NH2:9])[n:10]1 | N#Cc1ccc([N+](=O)[O-])c(N)n1 | N#Cc1ccc(N)c(N)n1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[N;D1;H2:5]):[#7;a:6]:[c:7]>>[N;D1;H2:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 3 | HOUR | 2-[4-(3,4-Dichloro-phenoxy)-phenyl]-1H-imidazo[4,5-b]pyridine-5-carboxylic acid amide. A flask containing 6-amino-5-nitro-pyridine-2-carbonitrile (67 mg, 0.40 mmol), 10% palladium on carbon (catalytic) and ethanol (2.0 mL) was put under an atmosphere of H2 using a balloon. The mixture was stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | [Pd].C(C)O | null | 3 | N#Cc1ccc([N+](=O)[O-])c(N)n1>[Pd].C(C)O>N#Cc1ccc(N)c(N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ae7c85dcc914422a8b0b8fde6dc8647 | N#Cc1ccc2[nH]c(-c3ccc(Oc4ccc(Cl)c(Cl)c4)cc3)nc2n1.O=Cc1ccc(Oc2ccc(Cl)c(Cl)c2)cc1>>NC(=O)c1ccc2[nH]c(-c3ccc(Oc4ccc(Cl)c(Cl)c4)cc3)nc2n1 | NC=1C=CC(=NC1N)C#N.ClC=1C=C(OC2=CC=C(C=O)C=C2)C=CC1Cl.CN(C(C)=O)C.ClC=1C=C(OC2=CC=C(C=C2)C=2NC=3C(=NC(=CC3)C#N)N2)C=CC1Cl>>ClC=1C=C(OC2=CC=C(C=C2)C=2NC=3C(=NC(=CC3)C(=O)N)N2)C=CC1Cl | [N:1]#[C:2][c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([O:14][c:15]4[cH:16][cH:17][c:18]([Cl:19])[c:20]([Cl:21])[cH:22]4)[cH:23][cH:24]3)[n:25][c:26]2[n:27]1.Clc1ccc(Oc2ccc(C=[O:3])cc2)cc1Cl>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([O:14][c:15]4[cH:16][c... | N#Cc1ccc2[nH]c(-c3ccc(Oc4ccc(Cl)c(Cl)c4)cc3)nc2n1.O=Cc1ccc(Oc2ccc(Cl)c(Cl)c2)cc1 | NC(=O)c1ccc2[nH]c(-c3ccc(Oc4ccc(Cl)c(Cl)c4)cc3)nc2n1 | null | null | O.[OH-].[Na+] | Miscellaneous | OtherReaction | 38473d65287697bacdad8a7b056914277e32da57df3acbc08d05ff2609af29fd | e976a573cc0fcfe5bcdced9e9aff2126e2e85772ccca42fd78bff9c131b70e83 | c1ccc(Oc2ccc(-c3nc4ncccc4[nH]3)cc2)cc1 | Cl-c1:c:c:c(-O-c2:c:c:c(-C=[O;H0;D1;+0:1]):c:c:2):c:c:1-Cl.[#7;a:2]:[c:3](:[#7;a:4]:[c:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]):[c:9]:[#7;a:10]>>[#7;a:2]:[c:3](:[#7;a:4]:[c:5](-[C;H0;D3;+0:6](-[NH2;D1;+0:7])=[O;H0;D1;+0:1]):[c:8]):[c:9]:[#7;a:10] | 94.6 | [{"value": 94.0, "product": "ClC=1C=C(OC2=CC=C(C=C2)C=2NC=3C(=NC(=CC3)C(=O)N)N2)C=CC1Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.6, "product": "ClC=1C=C(OC2=CC=C(C=C2)C=2NC=3C(=NC(=CC3)C(=O)N)N2)C=CC1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 24 | HOUR | 2-[4-(3,4-Dichloro-phenoxy)-phenyl]-1H-imidazo[4,5-b]pyridine-5-carboxylic acid amide. A flask containing 6-amino-5-nitro-pyridine-2-carbonitrile (67 mg, 0.40 mmol), 10% palladium on carbon (catalytic) and ethanol (2.0 mL) was put under an atmosphere of H2 using a balloon. The mixture was stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aldehyde.Ether.Nitrile | Primary amide | c1ccccc1.c1ccccc1 | null | c1cnc2nc[nH]c2c1.c1ccccc1.c1ccccc1 | HCl | O.[OH-].[Na+] | 120 | 24 | N#Cc1ccc2[nH]c(-c3ccc(Oc4ccc(Cl)c(Cl)c4)cc3)nc2n1.O=Cc1ccc(Oc2ccc(Cl)c(Cl)c2)cc1>O.[OH-].[Na+]>NC(=O)c1ccc2[nH]c(-c3ccc(Oc4ccc(Cl)c(Cl)c4)cc3)nc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc0a2177da05457c832f6830b0535dce | NC(=O)c1ccc(N)c(N)c1.Nc1ccc(S(N)(=O)=O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1>>NS(=O)(=O)c1ccc2[nH]c(-c3ccc(Oc4ccc5ccccc5c4)cc3)nc2c1 | FC1=CC=C(OC2=CC=C(C=O)C=C2)C=C1.NC=1C=C(C=CC1N)S(=O)(=O)N.NC=1C=C(C(=O)N)C=CC1N>>C1=C(C=CC2=CC=CC=C12)OC1=CC=C(C=C1)C1=NC2=C(N1)C=CC(=C2)S(=O)(=O)N | Nc1c[c:21]([C:20](N)=O)[cH:22][cH:23]c1N.[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:29]([NH2:28])[cH:30]1.O=[CH:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19](F)[cH:24][cH:25]2)[cH:26][cH:27]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[nH:9][c:10](-[c:11]3[cH:12][cH:13][... | NC(=O)c1ccc(N)c(N)c1.Nc1ccc(S(N)(=O)=O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1 | NS(=O)(=O)c1ccc2[nH]c(-c3ccc(Oc4ccc5ccccc5c4)cc3)nc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e5075026627231d073a25a05046f833469f27df49a9f3ef757543e8ac4c05b02 | 40f1e50ea82c16740a65162deb303e490e5736faef43c3e243b1134bf8d54295 | c1ccc2cc(Oc3ccc(-c4nc5ccccc5[nH]4)cc3)ccc2c1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.O=[CH;D2;+0:7]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].N-[C;H0;D3;+0:13](=O)-[c;H0;D3;+0:14]1:[c:15]:[cH;D2;+0:16]:c(-N):c(-N):c:1.[NH2;D1;+0:17]-[c:18](:[c:19]):[c:20](-[NH2;D1;+0:21]):[c:22]>>[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1]2:[cH;D2;+0:13]:[cH;D2;+0:14]:[c... | null | [] | null | null | null | null | This compound was prepared according to the methods described in Example 22 and Scheme 3, substituting 4-(naphthalen-2-yloxy)-benzaldehyde for 4-(4-fluoro-phenoxy)-benzaldehyde, and 3,4-diamino-benzenesulfonamide for 3,4-diaminobenzamide.
Conditions: See reaction.notes.procedure_details.
Workup: This compound was prepa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Primary amide.Primary amine.Primary amine.Primary amine.Primary amine | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccc2ccccc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1.c1ccc2ccccc2c1 | HF | null | null | null | NC(=O)c1ccc(N)c(N)c1.Nc1ccc(S(N)(=O)=O)cc1N.O=Cc1ccc(Oc2ccc(F)cc2)cc1>>NS(=O)(=O)c1ccc2[nH]c(-c3ccc(Oc4ccc5ccccc5c4)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b69f37ad842d46b3aeb6be2812aebbb8 | O=C(OCc1ccccc1)N1CC=CCC1.O=C(OO)c1cccc(Cl)c1>>O=C(OCc1ccccc1)N1CCC2OC2C1 | N1(CCC=CC1)C(=O)OCC1=CC=CC=C1.ClC=1C=C(C(=O)OO)C=CC1.CCCCCC.C(C)(=O)OCC>>C12CN(CCC2O1)C(=O)OCC1=CC=CC=C1 | [O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]=[CH:16][CH2:17]1.O=C(O[OH:15])c1cccc(Cl)c1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]2[O:15][CH:16]2[CH2:17]1 | O=C(OCc1ccccc1)N1CC=CCC1.O=C(OO)c1cccc(Cl)c1 | O=C(OCc1ccccc1)N1CCC2OC2C1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 3b45a1ce172e737dc524e1c5169806f7804897994baa710a8d301697bf4df36f | c40ffbbc3249442e5ee39aaa69a55be7ac2fa45f48637395e415c565c1288454 | O=C(OCc1ccccc1)N1CCC2OC2C1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]1-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-1>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]1-[C:6]-[C:7]-[CH;D3;+0:8]2-[O;H0;D2;+0:1]-[CH;D3;+0:9]-2-[C:10]-1 | null | [] | null | null | null | null | A stirred solution of benzyl 3,6-dihydropyridine-1(2H)-carboxylate (20.0 g, 92.0 mmol) in dichloromethane (280 ml) was cooled to 0° C. A solution of m-chloroperoxybenzoic acid (22.5 g, approx. 130 mmol) in dichloromethane (560 ml) was added drop-wise and the resulting colourless reaction mixture warmed to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | Ether | C1=CC[NH]CC1.c1ccccc1 | C1CC2OC2C[NH]1 | c1ccccc1.C1CC2OC2C[NH]1 | HCl | ClCCl | null | null | O=C(OCc1ccccc1)N1CC=CCC1.O=C(OO)c1cccc(Cl)c1>ClCCl>O=C(OCc1ccccc1)N1CCC2OC2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7baff472628c4fd88598f675370fa9fd | Cc1cccc(O)c1C.O=C(OCc1ccccc1)N1CCC2OC2C1>>Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C | C12CN(CCC2O1)C(=O)OCC1=CC=CC=C1.CC1=C(C=CC=C1C)O.[OH-].[Na+].[OH-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N1C[C@H]([C@@H](CC1)OC1=C(C(=CC=C1)C)C)O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:7])[c:25]1[CH3:26].[CH:8]12[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[CH2:22][CH:23]1[O:24]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][C@@H:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][c... | Cc1cccc(O)c1C.O=C(OCc1ccccc1)N1CCC2OC2C1 | Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C | null | null | C(C)#N.[Cl-].[Na+].O.O | Heteroatom Alkylation and Arylation | OtherReaction | bb8a59912df33eb4894501658fa75b47f44d0cef1868e510b68ee039cf0ab21b | d65f28c52f0777a08a008cfdcfc030aaa24bdbbd95c8114c9f5ad2abd4641bd1 | O=C(OCc1ccccc1)N1CCC(Oc2ccccc2)CC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[CH;D3;+0:7]2-[O;H0;D2;+0:8]-[CH;D3;+0:9]-2-[C:10]-1.[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C@@H;D3;+0:7](-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C@H;D3;+0:9](-[OH;D1;+0:8])-[C:10]-1 | 51.4 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@H]([C@@H](CC1)OC1=C(C(=CC=C1)C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.4, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@H]([C@@H](CC1)OC1=C(C(=CC=C1)C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (21.0 g, 92.0 mmol) was added to a stirred solution of 2,3-dimethylphenol (23.0 g, 188 mmol) and aqueous sodium hydroxide (100 ml, 2N, 200 mmol) in acetonitrile (400 ml). The reaction mixture was heated at reflux for 14 h. On cooling to room temperature, the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Secondary alcohol | C1CC2OC2C[NH]1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | C(C)#N.[Cl-].[Na+].O.O | null | null | Cc1cccc(O)c1C.O=C(OCc1ccccc1)N1CCC2OC2C1>C(C)#N.[Cl-].[Na+].O.O>Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96b3a4f7aed34438ba947e698b0b69ad | Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C>>Cc1cccc(O[C@@H]2CCNC[C@H]2O)c1C | C(C)OCC.CC1=C(O[C@H]2[C@@H](CN(CC2)C(=O)OCC2=CC=CC=C2)O)C=CC=C1C.[H][H]>>CC1=C(O[C@H]2[C@@H](CNCC2)O)C=CC=C1C | O=C(OCc1ccccc1)[N:11]1[CH2:10][CH2:9][C@@H:8]([O:7][c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:15]2[CH3:16])[C@H:13]([OH:14])[CH2:12]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][C@@H:8]2[CH2:9][CH2:10][NH:11][CH2:12][C@H:13]2[OH:14])[c:15]1[CH3:16] | Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C | Cc1cccc(O[C@@H]2CCNC[C@H]2O)c1C | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | ce0208fabe82d1244d7db7b6f7627b1b39a8cf3492e02720426849e93718e81c | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccc(OC2CCNCC2)cc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 50 | [{"value": 50.0, "product": "CC1=C(O[C@H]2[C@@H](CNCC2)O)C=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "CC1=C(O[C@H]2[C@@H](CNCC2)O)C=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of trans-benzyl 4-(2,3-dimethylphenoxy)-3-hydroxypiperidine-1-carboxylate (3.5 g, 9.8 mmol) in methanol (50 ml) was added to 5% palladium on charcoal (350 mg) under an atmosphere of nitrogen. The vessel was placed under an atmosphere of hydrogen and stirred vigorously until hydrogen uptake ceased. The result... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | [Pd].CO | null | null | Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C>[Pd].CO>Cc1cccc(O[C@@H]2CCNC[C@H]2O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-396c21b53fe14c60a2218777356825ad | Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C>>Cc1cccc(OC2CCN(C(=O)OCc3ccccc3)CC2=O)c1C | C(C)N(CC)CC.CS(=O)C.C(C(=O)Cl)(=O)Cl.C(C1=CC=CC=C1)OC(=O)N1C[C@H]([C@@H](CC1)OC1=C(C(=CC=C1)C)C)O>>CC1=C(OC2C(CN(CC2)C(=O)OCC2=CC=CC=C2)=O)C=CC=C1C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][C@@H:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[CH2:22][C@H:23]2[OH:24])[c:25]1[CH3:26]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:... | Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C | Cc1cccc(OC2CCN(C(=O)OCc3ccccc3)CC2=O)c1C | null | null | ClCCl.O | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | eb1454704a72f81f212192eafcb78e0711de77dd6074b9d7e49d38205debb755 | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CN(C(=O)OCc2ccccc2)CCC1Oc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C@@H;D3;+0:7](-[#8:8]-[c:9])-[C@H;D3;+0:10](-[OH;D1;+0:11])-[C:12]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[CH;D3;+0:7](-[#8:8]-[c:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12]-1 | 99.2 | [{"value": 99.0, "product": "CC1=C(OC2C(CN(CC2)C(=O)OCC2=CC=CC=C2)=O)C=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "CC1=C(OC2C(CN(CC2)C(=O)OCC2=CC=CC=C2)=O)C=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -60 | CELSIUS | 10 | MINUTE | A solution of oxalyl chloride (3.5 ml, 40 mmol, 1.1 eq.) in dichloromethane (350 ml) was cooled to −60° C. (internal temp.) and treated drop-wise with dimethyl sulfoxide (5.18 ml, 73.0 mmol, 2 eq.). On completion of addition the reaction mixture was stirred at −60° C. for 5 min. before drop-wise addition of a solution ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | ClCCl.O | -60 | 0.166667 | Cc1cccc(O[C@@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C>ClCCl.O>Cc1cccc(OC2CCN(C(=O)OCc3ccccc3)CC2=O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-973ad7ec4b5643c7b0572e224911b650 | Cc1cccc(OC2CCN(C(=O)OCc3ccccc3)CC2=O)c1C>>Cc1cccc(O[C@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C | CC1=C(OC2C(CN(CC2)C(=O)OCC2=CC=CC=C2)=O)C=CC=C1C.CCC([BH-](C(CC)C)C(CC)C)C.[K+]>>CC1=C(O[C@@H]2[C@@H](CN(CC2)C(=O)OCC2=CC=CC=C2)O)C=CC=C1C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[CH2:22][C:23]2=[O:24])[c:25]1[CH3:26]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][C@H:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20]... | Cc1cccc(OC2CCN(C(=O)OCc3ccccc3)CC2=O)c1C | Cc1cccc(O[C@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | c5c426998ef8289eab8bc31f16e2cce4176e0d9dc4e6b9619a0e750a805cc770 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C(OCc1ccccc1)N1CCC(Oc2ccccc2)CC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[CH;D3;+0:7](-[#8:8]-[c:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C@H;D3;+0:7](-[#8:8]-[c:9])-[C@H;D3;+0:10](-[OH;D1;+0:11])-[C:12]-1 | 50.3 | [{"value": 50.0, "product": "CC1=C(O[C@@H]2[C@@H](CN(CC2)C(=O)OCC2=CC=CC=C2)O)C=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "CC1=C(O[C@@H]2[C@@H](CN(CC2)C(=O)OCC2=CC=CC=C2)O)C=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of benzyl 4-(2,3-dimethylphenoxy)-3-oxopiperidine-1-carboxylate (10.0 g, 28.0 mmol) in tetrahydrofuran (60 ml) was treated at room temperature with K-selectride (10.0M in tetrahydrofuran, 56 ml, 56.0 mmol). On completion of addition the mixture was stirred at room temperature for 18 h. The mixture was concen... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | O1CCCC1 | null | 18 | Cc1cccc(OC2CCN(C(=O)OCc3ccccc3)CC2=O)c1C>O1CCCC1>Cc1cccc(O[C@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c573509549f044fb815c0bbb196f3969 | Cc1cccc(O[C@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C>>Cc1cccc(O[C@H]2CCNC[C@H]2O)c1C | C(C)OCC.CC1=C(O[C@@H]2[C@@H](CN(CC2)C(=O)OCC2=CC=CC=C2)O)C=CC=C1C.[H][H]>>CC1=C(O[C@@H]2[C@@H](CNCC2)O)C=CC=C1C | O=C(OCc1ccccc1)[N:11]1[CH2:10][CH2:9][C@H:8]([O:7][c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:15]2[CH3:16])[C@H:13]([OH:14])[CH2:12]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][C@H:8]2[CH2:9][CH2:10][NH:11][CH2:12][C@H:13]2[OH:14])[c:15]1[CH3:16] | Cc1cccc(O[C@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C | Cc1cccc(O[C@H]2CCNC[C@H]2O)c1C | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | ce0208fabe82d1244d7db7b6f7627b1b39a8cf3492e02720426849e93718e81c | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccc(OC2CCNCC2)cc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 67.8 | [{"value": 67.0, "product": "CC1=C(O[C@@H]2[C@@H](CNCC2)O)C=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "CC1=C(O[C@@H]2[C@@H](CNCC2)O)C=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of cis-benzyl 4-(2,3-dimethylphenoxy)-3-hydroxypiperidine-1-carboxylate (5.0 g, 14.0 mmol) in methanol (60 ml) was added to 5% palladium on charcoal (500 mg) under an atmosphere of nitrogen. The vessel was placed under an atmosphere of hydrogen and stirred vigorously until hydrogen uptake ceased. The resulti... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | [Pd].CO | null | null | Cc1cccc(O[C@H]2CCN(C(=O)OCc3ccccc3)C[C@H]2O)c1C>[Pd].CO>Cc1cccc(O[C@H]2CCNC[C@H]2O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9c4481bb48a47a886927688fde45bbe | Cc1cccc([C@@H]2CCNC[C@@H]2O)c1C.Cc1cccc([C@H]2CCNC[C@H]2O)c1C>>Cc1cccc(OC2CCNCC2O)c1C | CC1=C(C=CC=C1C)[C@H]1[C@@H](CNCC1)O.CC1=C(C=CC=C1C)[C@@H]1[C@@H](CNCC1)O.CC1=C(C=CC=C1C)[C@H]1[C@H](CNCC1)O.CC1=C(C=CC=C1C)[C@@H]1[C@H](CNCC1)O>>CC1=C(OC2C(CNCC2)O)C=CC=C1C | [C@@H]1([c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:15]2[CH3:16])[CH2:9][CH2:10][NH:11][CH2:12][C@@H:13]1[OH:14].Cc1cccc([C@H]2CCNC[C@H:8]2[OH:7])c1C>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]2[OH:14])[c:15]1[CH3:16] | Cc1cccc([C@@H]2CCNC[C@@H]2O)c1C.Cc1cccc([C@H]2CCNC[C@H]2O)c1C | Cc1cccc(OC2CCNCC2O)c1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1b25e45d396e9c0ced225d820a8ceaf13be14b7e03cd644e1c97c0031412c26d | 3c33ee7e8620215cdaf497cf199c7a1ad4a7c326860e108d12ae7b3ecae18255 | c1ccc(OC2CCNCC2)cc1 | null | null | [] | null | null | null | null | Retention times were as follows: (3S,4R)-4-(2,3-dimethylphenyl)-3-hydroxypiperidine, 14.5 minutes; (3R,4S)-4-(2,3-dimethylphenyl)-3-hydroxypiperidine, 16.5 minutes; (3R,4R)-4-(2,3-dimethylphenyl)-3-hydroxypiperidine, 15 minutes; and nM (3S,4S)-4-(2,3-dimethylphenyl)-3-hydroxypiperidine, 17 minutes. The identification o... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol.Secondary amine | Ether.Secondary alcohol | c1ccccc1.C1CCNCC1.c1ccccc1.C1CCNCC1 | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CCNCC1 | Other | null | null | null | Cc1cccc([C@@H]2CCNC[C@@H]2O)c1C.Cc1cccc([C@H]2CCNC[C@H]2O)c1C>>Cc1cccc(OC2CCNCC2O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9ddc22aff564f9bb539977507e82d66 | Nc1c(Br)cc([N+](=O)[O-])cc1Br>>O=[N+]([O-])c1cc(Br)cc(Br)c1 | BrC1=C(N)C(=CC(=C1)[N+](=O)[O-])Br.OS(=O)(=O)O.N(=O)[O-].[Na+]>>BrC1=CC(=CC(=C1)[N+](=O)[O-])Br | N[c:8]1[c:6]([Br:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:11][c:9]1[Br:10]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][c:9]([Br:10])[cH:11]1 | Nc1c(Br)cc([N+](=O)[O-])cc1Br | O=[N+]([O-])c1cc(Br)cc(Br)c1 | null | null | C(C)O | Reduction | OtherReaction | a069304de6b46c6d557b2e80c544464adc3bb98001f26c098e87c25f29d552f9 | a4f16f822d2806606c05d0c4baa1761ad37a11006840dde863a01a253bdff5dd | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2](-[Br;D1;H0:3]):[c:4]):[c:5](-[Br;D1;H0:6]):[c:7]>>[Br;D1;H0:6]-[c:5](:[c:7]):[cH;D2;+0:1]:[c:2](-[Br;D1;H0:3]):[c:4] | 93 | [{"value": 93.0, "product": "BrC1=CC(=CC(=C1)[N+](=O)[O-])Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "BrC1=CC(=CC(=C1)[N+](=O)[O-])Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (The named compound was synthesized according to Dumont, Bull. Soc. Chim. Bel., 505 (1995). This compound is also commercially available from Karl Industries, Aurora, Ohio.) To a suspension of 2,6-dibromo-4-nitroaniline (75.0 g, 254 mmol) in ethanol (1 L) was added H2SO4 (100 mL). The mixture was heated to reflux and s... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)O | null | null | Nc1c(Br)cc([N+](=O)[O-])cc1Br>C(C)O>O=[N+]([O-])c1cc(Br)cc(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e140c413254442d4bbef054ff1860151 | CN(C)C(=O)N(C)C.O=[N+]([O-])c1cc(Br)cc(Br)c1.[OH-]>>Brc1cc(Br)cc(OCc2ccccc2)c1 | BrC1=CC(=CC(=C1)[N+](=O)[O-])Br.[OH-].[K+].CN(C(N(C)C)=O)C>>BrC=1C=C(C=C(C1)Br)OCC1=CC=CC=C1 | O=[C:2](N([CH3:7])[CH3:12])N([CH3:3])[CH3:14].O=[N+]([O-])[c:9]1[cH:6][c:4]([Br:5])[cH:15][c:10]([Br:1])[cH:11]1.[OH-:8]>>[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1 | CN(C)C(=O)N(C)C.O=[N+]([O-])c1cc(Br)cc(Br)c1.[OH-] | Brc1cc(Br)cc(OCc2ccccc2)c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | Aromatic Heterocycle Formation | OtherReaction | 39730c04ca2b5a982ac6a3a3e29fa56cee513216d32a08dffb9e06195509a888 | 7682ae28b24d6a4254d9e6cdb97956c47d58fd8b43dbcd58057fb712f57afb50 | c1ccc(COc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-N(-[CH3;D1;+0:2])-[CH3;D1;+0:3])-N(-[CH3;D1;+0:4])-[CH3;D1;+0:5].O=[N+](-[O-])-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[Br;H0;D1;+0:9]):[cH;D2;+0:10]:[c;H0;D3;+0:11](-[Br;D1;H0:12]):[cH;D2;+0:13]:1.[OH-;D0:14]>>[Br;D1;H0:12]-[c;H0;D3;+0:11]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[Br;H0;D1;+0:9]):[c:15]:[c... | 92 | [{"value": 92.0, "product": "BrC=1C=C(C=C(C1)Br)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | (According to Effenberger, Chem. Ber. 163 (1991).) 1,3-dibromo-5-nitrobenzene (2.81 g, 10.0 mmol), freshly powdered potassium hydroxide (1.00 g, 17.8 mmol) and tetrabutylammonium bromide (0.32 g, 1.00 mmol) were dissolved in tetramethyl urea (TMU, 8 mL). Oxygen was bubbled through the reaction mixture for 5 min and a s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Urea.Nitro group | Aromatic halide.Aromatic halide.Ether | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | 6 | CN(C)C(=O)N(C)C.O=[N+]([O-])c1cc(Br)cc(Br)c1.[OH-]>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>Brc1cc(Br)cc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d3acff8689841b194edf640c7e83d10 | COc1ccc(CO)cc1.O=[N+]([O-])c1cc(Br)cc(Br)c1>>COc1ccc(COc2cc(Br)cc(Br)c2)cc1 | COC=1C=CC(=CC1)CO.BrC1=CC(=CC(=C1)[N+](=O)[O-])Br.[OH-].[K+]>>BrC=1C=C(C=C(C1)Br)OCC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:17][cH:18]1.O=[N+]([O-])[c:9]1[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]2)[cH:17][cH:18]1 | COc1ccc(CO)cc1.O=[N+]([O-])c1cc(Br)cc(Br)c1 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C(N(C)C)=O)C | Functional Group Interconversion | OtherReaction | 585e0ff0de8fd5f82bfaab47faba0014fb24285662aa50a5e33791db94cefd4b | 3990f9215b5a078e088ba5bbd0b8243e92e0f699f4ee1f20fbddffff29ec99ce | c1ccc(COc2ccccc2)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[C:7]-[c:8]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[C:7]-[c:8]):[c:4]:[c:5] | 74.4 | [{"value": 74.4, "product": "BrC=1C=C(C=C(C1)Br)OCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 1,3-dibromo-5-nitrobenzene (30.0 g, 107 mmol), freshly powdered potassium hydroxide (10.8 g, 192 mmol) and tetrabutylammonium bromide (3.42 g, 10.7 mmol) were dissolved in tetramethyl urea (TMU, 90 mL). A solution of p-methoxybenzyl alcohol (17.8 g, 128 mmol) in TMU (30 mL) was added drop-wise at room temperature over ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C(N(C)C)=O)C | null | 48 | COc1ccc(CO)cc1.O=[N+]([O-])c1cc(Br)cc(Br)c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C(N(C)C)=O)C>COc1ccc(COc2cc(Br)cc(Br)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb7f12fb6a90449b92cf25742e870b2d | Brc1cc(Br)cc(OCc2ccccc2)c1.Nc1cccnc1>>Brc1cc(Nc2cccnc2)cc(OCc2ccccc2)c1 | CCOC(=O)C.CCCCCCC.BrC=1C=C(C=C(C1)Br)OCC1=CC=CC=C1.NC=1C=NC=CC1.CC(C)([O-])C.[Na+]>>C(C1=CC=CC=C1)OC=1C=C(C=C(C1)Br)NC=1C=NC=CC1 | Br[c:4]1[cH:3][c:2]([Br:1])[cH:22][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:12]1.[NH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1>>[Br:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1 | Brc1cc(Br)cc(OCc2ccccc2)c1.Nc1cccnc1 | Brc1cc(Nc2cccnc2)cc(OCc2ccccc2)c1 | null | C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd] | C1(=CC=CC=C1)C.[Cl-].[Na+].O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2cccc(Nc3cccnc3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]):[c:4]:[c:5] | 41 | [{"value": 41.0, "product": "C(C1=CC=CC=C1)OC=1C=C(C=C(C1)Br)NC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.5, "product": "C(C1=CC=CC=C1)OC=1C=C(C=C(C1)Br)NC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 10 | MINUTE | An oven-dried flask was charged with (±)-BINAP (1.05 g, 1.68 mmol), Pd2(dba)3 CHCl3-complex (580 mg, 0.56 mmol) and then flushed with argon. Degassed toluene (28 mL) was added and the solution was stirred for 10 min. The catalyst solution was added to a mixture of 3,5-dibromo-1-benzyloxybenzene (38.3 g, 112 mmol), 3-am... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HBr | C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].C1(=CC=CC=C1)C.[Cl-].[Na+].O | 85 | 0.166667 | Brc1cc(Br)cc(OCc2ccccc2)c1.Nc1cccnc1>C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].C1(=CC=CC=C1)C.[Cl-].[Na+].O>Brc1cc(Nc2cccnc2)cc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9655981e253346789505a2b9054eb072 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.Nc1cccnc1>>COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1 | CCOC(=O)C.BrC=1C=C(C=C(C1)Br)OCC1=CC=C(C=C1)OC.NC=1C=NC=CC1.C(C)(C)(C)[O-].[Na+]>>COC1=CC=C(COC=2C=C(C=C(C2)Br)NC=2C=NC=CC2)C=C1 | Br[c:14]1[cH:13][c:11]([Br:12])[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]2)[cH:22]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][n:20][cH:21]3)[cH:22]2)[... | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.Nc1cccnc1 | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1 | null | C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd] | CCOC(=O)C.CCCCCCC.C1(=CC=CC=C1)C.[Cl-].[Na+].O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2cccc(Nc3cccnc3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]):[c:4]:[c:5] | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 10 | MINUTE | An oven-dried flask was charged with (±)-BINAP (504 mg, 0.81 mmol), Pd2(dba)3 CHCl3-complex (278 mg, 0.27 mmol) and then flushed with argon. Degassed toluene (50 mL) was added and the solution was stirred for 10 min. A second oven-dried flask was charged with 3,5-dibromo-1-p-methoxy-benzyloxybenzene (20.0 g, 53.8 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccncc1 | HBr | C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].CCOC(=O)C.CCCCCCC.C1(=CC=CC=C1)C.[Cl-].[Na+].O | 90 | 0.166667 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.Nc1cccnc1>C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].CCOC(=O)C.CCCCCCC.C1(=CC=CC=C1)C.[Cl-].[Na+].O>COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-582ddb996ddd4c0bb4300f2ed1efe680 | COc1ccc(COc2cc(Nc3cccnc3)cc(-c3cccc4sccc34)c2)cc1>>Oc1cc(Nc2cccnc2)cc(-c2cccc3sccc23)c1 | S1C2=C(C=C1)C(=CC=C2)C=2C=C(C=C(C2)OCC2=CC=C(C=C2)OC)NC=2C=NC=CC2.C1(=CC=CC=C1)SC.FC(C(=O)O)(F)F>>S1C2=C(C=C1)C(=CC=C2)C=2C=C(C=C(C2)NC=2C=NC=CC2)O | COc1ccc(C[O:1][c:2]2[cH:3][c:4]([NH:5][c:6]3[cH:7][cH:8][cH:9][n:10][cH:11]3)[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]4[s:19][cH:20][cH:21][c:22]34)[cH:23]2)cc1>>[OH:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][c:18]3[s:19][cH:20][cH:21][c:22]23)[c... | COc1ccc(COc2cc(Nc3cccnc3)cc(-c3cccc4sccc34)c2)cc1 | Oc1cc(Nc2cccnc2)cc(-c2cccc3sccc23)c1 | null | null | C(Cl)Cl | Reduction | OtherReaction | 8a4606e79840bb3d9b3a2e0b7d9ed5648d76ae6cbcc894506db9722ac2624f9a | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1cncc(Nc2cccc(-c3cccc4sccc34)c2)c1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):c:c:1>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 66.7 | [{"value": 58.0, "product": "S1C2=C(C=C1)C(=CC=C2)C=2C=C(C=C(C2)NC=2C=NC=CC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "S1C2=C(C=C1)C(=CC=C2)C=2C=C(C=C(C2)NC=2C=NC=CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | HOUR | [3-benzo[b]thiophen-4-yl-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine (35 mg, 0.08 mmol) was dissolved in CH2Cl2 (1 mL) and thioanisole (188 μL, 1.60 mmol) was added. The solution was cooled to 0° C. and trifluoroacetic acid (0.1 mL) was added. The reaction mixture was stirred at room temperature for 5 h and was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccncc1.c1ccc2sccc2c1 | HO- | C(Cl)Cl | 0 | 5 | COc1ccc(COc2cc(Nc3cccnc3)cc(-c3cccc4sccc34)c2)cc1>C(Cl)Cl>Oc1cc(Nc2cccnc2)cc(-c2cccc3sccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ded46bef1bef45f9a82d0d90149d9313 | COc1ccc(Cc2cc(Br)cc(Nc3cccnc3)c2)cc1.O=[N+]([O-])c1ccc2cc[nH]c2c1>>O=[N+]([O-])c1ccc2ccn(-c3cc(O)cc(Nc4cccnc4)c3)c2c1 | P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[N+](=O)([O-])C1=CC=C2C=CNC2=C1.CNCCNC.BrC=1C=C(C=C(C1)CC1=CC=C(C=C1)OC)NC=1C=NC=CC1>>[N+](=O)([O-])C1=CC=C2C=CN(C2=C1)C=1C=C(C=C(C1)NC=1C=NC=CC1)O | C[O:14]c1ccc(C[c:11]2[cH:12][c:13](Br)[cH:15][c:16]([NH:17][c:18]3[cH:19][cH:20][cH:21][n:22][cH:23]3)[cH:24]2)cc1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][nH:10][c:25]2[cH:26]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][n:10](-[c:11]3[cH:12][c:13]([OH:14])[cH:15][c:16]([NH:17][c:18]4[cH:... | COc1ccc(Cc2cc(Br)cc(Nc3cccnc3)c2)cc1.O=[N+]([O-])c1ccc2cc[nH]c2c1 | O=[N+]([O-])c1ccc2ccn(-c3cc(O)cc(Nc4cccnc4)c3)c2c1 | null | [Cu]I | C1(=CC=CC=C1)C.C(Cl)Cl | Functional Group Addition | OtherReaction | a32afc24d96451c382dc4201082b19044aee20ea0e571d31f34af06c379170ae | 8a5089a4a46e8f89fdbb977c3fed3a2378e3bcd5a197b8cfa9ddc8a8a34b2a51 | c1cncc(Nc2cccc(-n3ccc4ccccc43)c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-C-c2:c:c:c(-[O;H0;D2;+0:4]-C):c:c:2):[c:5]:[c:6]:[c:7]:1.[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[OH;D1;+0:4]-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-[n;H0;D3;+0:13]2:[c:12]:[c:11]:[c:10]:[c:9]:2:[c:8]):[c:5]:[c:6]:[c:7]:1 | null | [] | 110 | CELSIUS | null | null | The resin-bound (3-bromo-5-p-methoxybenzylphenyl)-3-pyridylamine described in Example 22 (200 mg, ca 0.12 mmol) was placed in a 50 mL glass reactor. Copper (I) iodide (0.6 mmol, 114 mg), potassium phosphate (127 mg, 0.6 mmol), toluene (5 mL), 6-nitroindole (0.6 mmol, 98 mg) and N,N′-dimethylethylenediamine (53 mg, 0.6 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1.c1ccncc1 | HBr | [Cu]I.C1(=CC=CC=C1)C.C(Cl)Cl | 110 | null | COc1ccc(Cc2cc(Br)cc(Nc3cccnc3)c2)cc1.O=[N+]([O-])c1ccc2cc[nH]c2c1>[Cu]I.C1(=CC=CC=C1)C.C(Cl)Cl>O=[N+]([O-])c1ccc2ccn(-c3cc(O)cc(Nc4cccnc4)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f204a4fc1199400a9a77315d8cc9ea00 | COc1ccc(COc2cc(C(=O)c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.NO>>COc1ccc(COc2cc(C(=NO)c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | COC1=CC=C(COC=2C=C(C=C(C2)C2=C3C=CN(C3=CC=C2)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C=2C=NC=CC2)C=C1.Cl.ON>>COC1=CC=C(COC=2C=C(C=C(C2)C2=C3C=CN(C3=CC=C2)[Si](C(C)C)(C(C)C)C(C)C)C(=NO)C=2C=NC=CC2)C=C1 | O=[C:12]([c:11]1[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44][cH:43]2)[cH:42][c:22](-[c:23]2[cH:24][cH:25][cH:26][c:27]3[c:28]2[cH:29][cH:30][n:31]3[Si:32]([CH:33]([CH3:34])[CH3:35])([CH:36]([CH3:37])[CH3:38])[CH:39]([CH3:40])[CH3:41])[cH:21]1)[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1.[NH2:13][... | COc1ccc(COc2cc(C(=O)c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.NO | COc1ccc(COc2cc(C(=NO)c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(c1cccnc1)c1cc(OCc2ccccc2)cc(-c2cccc3[nH]ccc23)c1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9].[NH2;D1;+0:10]-[O;D1;H1:11]>>[O;D1;H1:11]-[N;H0;D2;+0:10]=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | null | [] | null | null | 2 | HOUR | [3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone (50 mg, 0.085 mmol) and hydroxyamine hydrochloride (29 mg, 0.42 mmol) in 2 mL of ethanol was heated to reflux. After 2 hrs, the reaction was completed. The solvent was removed under reduced pressure. The crude product was re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1ccccc1.c1ccncc1.c1cccc2[nH]ccc12 | HO- | C(C)O | null | 2 | COc1ccc(COc2cc(C(=O)c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.NO>C(C)O>COc1ccc(COc2cc(C(=NO)c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c2653f0cac1492cbf088944d2dd581a | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(OCc4ccccc4)nc(Nc4cccnc4)n3)cccc21>>Oc1cc(-c2cccc3[nH]ccc23)nc(Nc2cccnc2)n1 | C(C1=CC=CC=C1)OC1=NC(=NC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC=1C=NC=CC1.C(C1=CC=CC=C1)OC1=NC(=NC(=C1)Cl)NC=1C=NC=CC1.C([O-])([O-])=O.[K+].[K+].CC1(OB(OC1(C)C)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C>>N1C=CC2=C(C=CC=C12)C1=CC(=NC(=N1)NC=1C=NC=CC1)O | CC(C)[Si](C(C)C)(C(C)C)[n:10]1[c:9]2[cH:8][cH:7][cH:6][c:5](-[c:4]3[cH:3][c:2]([O:1]Cc4ccccc4)[n:23][c:15]([NH:16][c:17]4[cH:18][cH:19][cH:20][n:21][cH:22]4)[n:14]3)[c:13]2[cH:12][cH:11]1>>[OH:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[nH:10][cH:11][cH:12][c:13]23)[n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:2... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(OCc4ccccc4)nc(Nc4cccnc4)n3)cccc21 | Oc1cc(-c2cccc3[nH]ccc23)nc(Nc2cccnc2)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.CN(C)C=O | Deprotection | OtherReaction | 495cb76f602ebd19a8a5962d26b650b172d6ae8b0c11815bbf9f60e06b9b1e13 | 5e40339a4a04757b519e3c89ecb7b8ce3defd2e5e05bc91c5ac27f57100aee42 | c1cncc(Nc2nccc(-c3cccc4[nH]ccc34)n2)c1 | C(-[O;H0;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)-c1:c:c:c:c:c:1.C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[c:12]:1:[c:13]>>[OH;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[c:13]:[c:12]1:[c:11]:[c:10]:[c:9]:[nH;D2;+0:8]:1 | null | [] | null | null | null | null | [4-Benzyloxy-6-(1-triisopropylsilanyl-1H-indol-4-yl)-pyrimidin-2-yl]-pyridin-3-yl-amine. DMF (1 mL) and dioxane (2 mL) were added through a septum to a nitrogen-purged microwave tube containing (4-benzyloxy-6-chloro-pyrimidin-2-yl)-pyridin-3-yl-amine (80 mg, 0.256 mmol), potassium carbonate (71 mg, 0.50 mmol), Pd(PPh3)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Silyl protective group | Aromatic alcohol | c1cccc2[nH]ccc12.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1.c1ccncc1 | Other | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.CN(C)C=O | null | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(OCc4ccccc4)nc(Nc4cccnc4)n3)cccc21>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.CN(C)C=O>Oc1cc(-c2cccc3[nH]ccc23)nc(Nc2cccnc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d26c78cbdef44779b108ae6e7f26c9c | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1.N#Cc1ccc2[nH]ccc2c1>>N#Cc1ccc2c(ccn2-c2cc(O)cc(Nc3cccnc3)c2)c1 | BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)NC=1C=NC=CC1.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].C(#N)C=1C=C2C=CNC2=CC1.CNCCNC>>OC=1C=C(C=C(C1)NC=1C=NC=CC1)N1C=CC2=CC(=CC=C12)C#N | COc1ccc(C[O:14][c:13]2[cH:12][c:11](Br)[cH:24][c:16]([NH:17][c:18]3[cH:19][cH:20][cH:21][n:22][cH:23]3)[cH:15]2)cc1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8][cH:9][nH:10]2)[cH:25]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8][cH:9][n:10]2-[c:11]2[cH:12][c:13]([OH:14])[cH:15][c:16]([NH:17][c:18]3[cH:19][cH:20]... | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1.N#Cc1ccc2[nH]ccc2c1 | N#Cc1ccc2c(ccn2-c2cc(O)cc(Nc3cccnc3)c2)c1 | null | [Cu]I | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 8246b8e0885ddf770fb4c8d79c1e3f38929caaa2e872d869c6b0b455195b8f06 | c3e82c812dc6c78070ba1f75e08effdbeaff4cd50c4337e2c1365f20b4956654 | c1cncc(Nc2cccc(-n3ccc4ccccc43)c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[O;H0;D2;+0:4]-C-c2:c:c:c(-O-C):c:c:2):[c:5]:[c:6]:[c:7]:1.[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[OH;D1;+0:4]-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:13]2:[c:12]:[c:11]:[c:10]:[c:9]:2:[c:8]):[c:7]:[c:6]:[c:5]:1 | 10.8 | [{"value": 10.8, "product": "OC=1C=C(C=C(C1)NC=1C=NC=CC1)N1C=CC2=CC(=CC=C12)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | [3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine (193 mg, ca 0.5 mmol) was placed in a 5 mL glass reactor. Copper (I) iodide (0.5 mmol, 96 mg), potassium phosphate (213 mg, 1 mmol), toluene (3 mL), 5-cyanoindole (1.0 mmol, 142 mg) and N,N′-dimethylethylenediamine (53 mg, 0.6 mmol) were added to the reactor, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccncc1 | HBr | [Cu]I.C1(=CC=CC=C1)C | 110 | null | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1.N#Cc1ccc2[nH]ccc2c1>[Cu]I.C1(=CC=CC=C1)C>N#Cc1ccc2c(ccn2-c2cc(O)cc(Nc3cccnc3)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-931461be7229496e836defd5785e4db4 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(Nc3ccc(OCc4ccccc4)nc3)c2)cc1>>COc1ccc(COc2cc(N)cc(Br)c2)cc1 | C(C1=CC=CC=C1)OC1=CC=C(C=N1)N.BrC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)Br.CC(C)(C)[O-].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=N1)NC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)Br>>BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)N | Br[c:11]1[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[cH:16][c:14]([Br:15])[cH:13]1.COc1ccc(COc2cc(Br)cc([NH:12]c3ccc(OCc4ccccc4)nc3)c2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([NH2:12])[cH:13][c:14]([Br:15])[cH:16]2)[cH:17][cH:18]1 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(Nc3ccc(OCc4ccccc4)nc3)c2)cc1 | COc1ccc(COc2cc(N)cc(Br)c2)cc1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8 | null | Heteroatom Alkylation and Arylation | OtherReaction | 285d763a51f37794cdad66c72d48d0d44a3fcbc0fdf73d0fca473c1c998f6180 | f9b3fc120e1f63fc61f4091f79b5f0d58358f7d72db88a5e5844c6ed41e6a76b | c1ccc(COc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-c1:c:c(-O-C-c2:c:c:c(-O-C):c:c:2):c:c(-[NH;D2;+0:6]-c2:c:c:c(-O-C-c3:c:c:c:c:c:3):n:c:2):c:1>>[NH2;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 47 | [{"value": 47.0, "product": "BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)N", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | (6-benzyloxy-pyridin-3-yl)-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-amine. A dry tube was charged with 6-benzyloxy-pyridin-3-ylamine (68 mg, 0.34 mmol), 1,3-dibromo-5-(4-methoxy-benzyloxy)-benzene (126 mg, 0.34 mmol), NaOtBu (46 mg, 0.48 mmol), Pd2(dba)3 (3.1 mg, 0.0034 mmol), BINAP (6.3 mg, 0.01 mmol) and degassed tol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether.Ether.Secondary amine | Primary amine | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8 | 120 | null | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(Nc3ccc(OCc4ccccc4)nc3)c2)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8>COc1ccc(COc2cc(N)c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d8a05038e0b418682bb41b4051f3946 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(Nc3ccc(OCc4ccccc4)nc3)c2)cc1>>Oc1cc(Nc2cccnc2O)cc(-c2cccc3[nH]ccc23)c1 | C(C1=CC=CC=C1)OC1=CC=C(C=N1)NC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)Br.CC1(OB(OC1(C)C)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C.[O-]P(=O)([O-])[O-].[K+].[K+].[K+].C(C1=CC=CC=C1)OC1=CC=C(C=N1)NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)OCC1=CC=C(C=C1)OC>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C(=NC=CC1)O | CC(C)[Si](C(C)C)(C(C)C)[n:20]1[c:19]2[cH:18][cH:17][cH:16][c:15](B3OC(C)(C)C(C)(C)O3)[c:23]2[cH:22][cH:21]1.COc1ccc(C[O:1][c:2]2[cH:3][c:4]([NH:5][c:6]3[cH:7][cH:8][c:9]([O:12]Cc4ccccc4)[n:10][cH:11]3)[cH:13][c:14](Br)[cH:24]2)cc1>>[OH:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]2[OH:12])[cH:13][c:14]... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(Nc3ccc(OCc4ccccc4)nc3)c2)cc1 | Oc1cc(Nc2cccnc2O)cc(-c2cccc3[nH]ccc23)c1 | null | Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1 | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | db8d541dfd7dc38b3b8482e14552e3171bc48f887dfd400dc975b9e9e284c679 | 199f12599629136c735d0ade11f454f145e4cbfd03347490ea78984a0acd7720 | c1cncc(Nc2cccc(-c3cccc4[nH]ccc34)c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]-[c:5]2:[c:6]:[c:7]:[c;H0;D3;+0:8](-[O;H0;D2;+0:9]-C-c3:c:c:c:c:c:3):[#7;a:10]:[cH;D2;+0:11]:2):[c:12]:[c:13](-[O;H0;D2;+0:14]-C-c2:c:c:c(-O-C):c:c:2):[c:15]:1.C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:16]1:[c:17]:[c:18]:[c:19]2:[c:20]:1:[c:21]:[c:22]:[c:23]:[c;H0;D3;+0:24]:2-B1... | 57.1 | [{"value": 57.1, "product": "OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C(=NC=CC1)O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | (6-benzyloxy-pyridin-3-yl)-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-amine. To a tube purged with nitrogen containing (6-benzyloxy-pyridin-3-yl)-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-amine (78 mg, 0.158 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Ether.Boronic ester.Silyl protective group | Aromatic alcohol.Aromatic alcohol | c1cccc2[nH]ccc12.B1OCCO1.c1ccccc1.c1ccccc1.c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HBr.B | Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1.O1CCOCC1 | 120 | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(Nc3ccc(OCc4ccccc4)nc3)c2)cc1>Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1.O1CCOCC1>Oc1cc(Nc2cccnc2O)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8d0d240a83c41eda633c9e7bf13f4cc | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(O)cc(Nc4ccc(O)nc4)c3)cccc21>>Oc1cc(Nc2ccc(O)nc2)cc(-c2cccc3[nH]ccc23)c1 | OC=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC=1C=CC(=NC1)O>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C=CC(=NC1)O | CC(C)[Si](C(C)C)(C(C)C)[n:20]1[c:19]2[cH:18][cH:17][cH:16][c:15](-[c:14]3[cH:13][c:4]([NH:5][c:6]4[cH:7][cH:8][c:9]([OH:10])[n:11][cH:12]4)[cH:3][c:2]([OH:1])[cH:24]3)[c:23]2[cH:22][cH:21]1>>[OH:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([OH:10])[n:11][cH:12]2)[cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][c:19]3[n... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(O)cc(Nc4ccc(O)nc4)c3)cccc21 | Oc1cc(Nc2ccc(O)nc2)cc(-c2cccc3[nH]ccc23)c1 | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | Deprotection | OtherReaction | 7c2e21594486284c07d91d3a35172f6f97c1f0e21d7ef6570d737987b23577df | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | c1cncc(Nc2cccc(-c3cccc4[nH]ccc34)c2)c1 | C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6]>>[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 1.5 | [{"value": 1.5, "product": "OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C=CC(=NC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 1.5, "product": "OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C=CC(=NC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-[3-hydroxy-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenylamino]-pyridin-2-ol (taken as 0.126 mmol) in TFA/CH2Cl2 (5 mL/5 mL)) was stirred at 0° C. for 1 h. The resulting mixture was concentrated, and saturated aqueous NaHCO3 was added. The pH was adjusted to around 7 and the mixture was extracted with E... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | Other | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(O)cc(Nc4ccc(O)nc4)c3)cccc21>C(=O)(C(F)(F)F)O.C(Cl)Cl>Oc1cc(Nc2ccc(O)nc2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da44352d4d494044ba354295353557ff | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.Oc1cccnc1>>COc1ccc(COc2cc(Br)cc(Oc3cccnc3)c2)cc1 | BrC=1C=C(C=C(C1)Br)OCC1=CC=C(C=C1)OC.OC=1C=NC=CC1.[H-].[Na+].[OH-].[NH4+]>>BrC=1C=C(OC=2C=NC=CC2)C=C(C1)OCC1=CC=C(C=C1)OC | Br[c:14]1[cH:13][c:11]([Br:12])[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]2)[cH:22]1.[OH:15][c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([O:15][c:16]3[cH:17][cH:18][cH:19][n:20][cH:21]3)[cH:22]2)[cH... | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.Oc1cccnc1 | COc1ccc(COc2cc(Br)cc(Oc3cccnc3)c2)cc1 | null | [Cu]=O | N1=C(C=C(C=C1C)C)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(COc2cccc(Oc3cccnc3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]):[c:4]:[c:5] | 25 | [{"value": 25.0, "product": "BrC=1C=C(OC=2C=NC=CC2)C=C(C1)OCC1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | 210 | CELSIUS | 10 | MINUTE | A mixture of the 3,5-dibromo-1-p-methoxy-benzyloxybenzene (250 mg, 0.672 mmol) and 3-hydroxypyridine (128 mg, 1.34 mmol) and 96 mg (0.67 mmol) copper oxide in 3 mL of collidine was treated with sodium hydride (27 mg, 0.67 mmol) in a stirred tube. After 10 minutes to allow off-gassing, the tube was sealed and the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccncc1 | HBr | [Cu]=O.N1=C(C=C(C=C1C)C)C.C(C)(=O)OCC | 210 | 0.166667 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.Oc1cccnc1>[Cu]=O.N1=C(C=C(C=C1C)C)C.C(C)(=O)OCC>COc1ccc(COc2cc(Br)cc(Oc3cccnc3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b47ffa855b54e379dbfcda0be4614a0 | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1.OB(O)c1ccc2c(c1)OCO2>>COc1ccc(COc2cc(Nc3cccnc3)cc(-c3ccc4c(c3)OCO4)c2)cc1 | B(C1=CC2=C(C=C1)OCO2)(O)O.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)NC=1C=NC=CC1>>O1COC2=C1C=CC(=C2)C=2C=C(C=C(C2)OCC2=CC=C(C=C2)OC)NC=2C=NC=CC2 | Br[c:20]1[cH:19][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][n:17][cH:18]2)[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][cH:31]2)[cH:30]1.OB(O)[c:21]1[cH:22][cH:23][c:24]2[c:25]([cH:26]1)[O:27][CH2:28][O:29]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14... | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1.OB(O)c1ccc2c(c1)OCO2 | COc1ccc(COc2cc(Nc3cccnc3)cc(-c3ccc4c(c3)OCO4)c2)cc1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | 4eaac3524feef0fac9270283493ac343cfbd88f66b23f78df9bf06d23e299fd5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(COc2cc(Nc3cccnc3)cc(-c3ccc4c(c3)OCO4)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]-[#8:11]>>[#8:11]-[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | 110 | CELSIUS | null | null | [3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine (MW=385.26, 193 mg, 0.5 mmol) was placed into a 10 mL microwave reaction tube and placed under a nitrogen atmosphere. 3,4-(Methylenedioxy)phenylboronic acid (MW=165.94, 124 mg, 0.75 mmol), 2-(di-t-butylphosphino)biphenyl (FW 298.41, 15 mg, 0.05 mmol), tris(dib... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccccc1.c1ccncc1.c1ccc2c(c1)OCO2 | HBr.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1 | 110 | null | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1.OB(O)c1ccc2c(c1)OCO2>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1>COc1ccc(COc2cc(Nc3cccnc3)cc(-c3ccc4c(c3)OCO4)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da9dd3df01f34036a31335f47bc8e43d | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(Nc3ccncc3)c2)cc1.Nc1ccncc1>>Oc1cc(Nc2ccncc2)cc(-c2cccc3[nH]ccc23)c1 | BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)NC1=CC=NC=C1.NC1=CC=NC=C1.BrC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)Br.CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C(C=CC=C51)P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(C)([O-])C.[Na+]>>N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)NC1=CC=NC=C1)O | COc1ccc(COc2c[c:14](Br)[cH:15][c:16](Br)[cH:17]2)cc1.COc1ccc(C[O:1][c:2]2[cH:3][c:4]([NH:5][c:6]3[cH:7][cH:8][n:9][cH:10][cH:11]3)[cH:12][c:13](Br)[cH:23]2)cc1.c1[c:18]([NH2:19])[cH:22][cH:21]n[cH:20]1>>[OH:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][c:18... | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(Nc3ccncc3)c2)cc1.Nc1ccncc1 | Oc1cc(Nc2ccncc2)cc(-c2cccc3[nH]ccc23)c1 | null | null | O1CCOCC1 | C-C Coupling | OtherReaction | c4525d84e43b85cea7e68da85eeb0dbbca68b725fcba237cdd82cb1ed50ccc9c | 8153db5c3bfc596b3ddf75a4bcf8f137ac58632dff07224972307439dcfb31bb | c1cc(Nc2ccncc2)cc(-c2cccc3[nH]ccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-Br):[cH;D2;+0:4]:c(-O-C-c2:c:c:c(-O-C):c:c:2):c:1.Br-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-C-c2:c:c:c(-O-C):c:c:2):[c:11]:1.[NH2;D1;+0:12]-[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:n:[cH;D2;+0:16]:c:1>>[OH;D1;+0:10]-[c:9]1:[c:11]:[c;H0;D3;+0:5](-[c;H0;D3;+0... | null | [] | 110 | CELSIUS | null | null | [3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-4-yl-amine. A solution of 4-aminopyridine (71 mg, 0.75 mmol), 1,3-dibromo-5-(4-methoxybenzyloxy)benzene (372.0 mg, 1.0 mmol), XantPhos (56 mg, 0.1 mmol), (dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), and sodium tert-butoxide (192 mg, 2.0 mmol) in dioxane (3 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Ether.Ether.Ether.Primary amine | Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HBr | O1CCOCC1 | 110 | null | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(Nc3ccncc3)c2)cc1.Nc1ccncc1>O1CCOCC1>Oc1cc(Nc2ccncc2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d77c24d3aeee4112bb43e55d41702be6 | CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C.CI.COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1>>Cn1ccc2c(-c3cc(O)cc(Nc4cccnc4)c3)cccc21.Cn1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21 | BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)NC=1C=NC=CC1.CC1(OB(OC1(C)C)C1=C2C=CNC2=CC=C1)C.CI>>CN1C=CC2=C(C=CC=C12)B1OC(C(O1)(C)C)(C)C.CN1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)NC=1C=NC=CC1)O | [nH:2]1[cH:3][cH:4][c:5]2[c:6]([B:31]3[O:32][C:33]([CH3:34])([CH3:35])[C:36]([CH3:37])([CH3:38])[O:39]3)[cH:21][cH:22][cH:23][c:24]12.I[CH3:25].Br[c:41]1[cH:8][c:9]([O:10][CH2:42][c:7]2[cH:20][cH:30][c:29](O[CH3:1])[cH:28][cH:27]2)[cH:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:40]1>>[CH3:1][n:2]1[c... | CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C.CI.COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1 | Cn1ccc2c(-c3cc(O)cc(Nc4cccnc4)c3)cccc21.Cn1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | af7a56d73766cb70c021ce4a40c52bc7e44bdab01e83278398b5aaf001b681c4 | 24cbf480b9aafe9766583c7f23142629e3af14b057f15f349d5bffd59d6c0b79 | c1cc(B2OCCO2)c2cc[nH]c2c1.c1cncc(Nc2cccc(-c3cccc4[nH]ccc34)c2)c1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[#7:4]-[c:5]:[c:6]:[#7;a:7]):[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12]2:[cH;D2;+0:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15](-O-[CH3;D1;+0:16]):[c:17]:[cH;D2;+0:18]:2):[cH;D2;+0:19]:1.I-[CH3;D1;+0:20].[#8:21]1-[C:22]-[C:23]-[#8:24]-[B;H0;D3;+0:25]-1-[c;H0;D3;+0:2... | null | [] | null | null | null | null | 1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole was prepared from 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole and methyl iodide, and was coupled with [3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine in the same manner as described for Example 25. Deprotection was carried ou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Boronic ester | Aromatic alcohol.Boronic ester | [B]1OCCO1.c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | c1ccccc1.c1cccc2[nH]ccc12.[B]1OCCO1.c1cccc2[nH]ccc12 | c1ccccc1.c1ccncc1.c1cccc2[nH]ccc12.[B]1OCCO1.c1cccc2[nH]ccc12 | HBr.I- | null | null | null | CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C.CI.COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1>>Cn1ccc2c(-c3cc(O)cc(Nc4cccnc4)c3)cccc21.Cn1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d5753192d0224faa86d0e163bf369cc3 | COc1cc(Br)cc(Br)c1.Nc1cccnc1>>COc1cc(Br)cc(Nc2cccnc2)c1 | BrC1=CC(=CC(=C1)OC)Br.N1=CC(=CC=C1)N.N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)OC)NC=1C=NC=CC1>>BrC=1C=C(C=C(C1)OC)NC=1C=NC=CC1 | Br[c:8]1[cH:7][c:5]([Br:6])[cH:4][c:3]([O:2][CH3:1])[cH:16]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[cH:16]1 | COc1cc(Br)cc(Br)c1.Nc1cccnc1 | COc1cc(Br)cc(Nc2cccnc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[#7;a:10]:[c:11] | null | [] | null | null | null | null | (3-Bromo-5-methoxy-phenyl)-pyridin-3-yl-amine was prepared from 1,3-dibromo-5-methoxy-benzene and pyridin-3-ylamine as described for Example 36. This material was converted to [3-(1H-indol-4-yl)-5-methoxy-phenyl]-pyridin-3-yl-amine by the method of Example 35. 1H NMR (400 MHz, CDCl3): δ 8.44 (d, J=2.7 Hz, 1H), 8.34 (br... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HBr | null | null | null | COc1cc(Br)cc(Br)c1.Nc1cccnc1>>COc1cc(Br)cc(Nc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2bf35fd8a86c4627a60c8cc3d7fda835 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(C)nc3)c2)cc1.Cc1ccc(C#N)cn1>>O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | Cl.[Li]CCCC.CCCCCC.BrC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)Br.BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)C(=O)C=1C=NC(=CC1)C.CC1=NC=C(C#N)C=C1.[OH-].[Na+]>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC(=CC1)CO | COc1ccc(C[O:8][c:21]2[cH:20][c:19](Br)[cH:18][c:17](Br)[cH:25]2)cc1.COc1ccc(C[O:14][c:13]2[cH:12][c:11]([C:2](=[O:1])[c:3]3[cH:4][cH:5][c:6]([CH3:7])[n:9][cH:10]3)[cH:26][c:16](Br)[cH:15]2)cc1.Cc1cc[c:24]([C:23]#[N:22])cn1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[n:9][cH:10]1)[c:11]1[cH:12][c:13]([OH:14])[cH... | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(C)nc3)c2)cc1.Cc1ccc(C#N)cn1 | O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | e948f15af83dadb9336ecab39fc7779aeb5785da8e178956da39ac376662b95f | 7a4ecf18617f425f716e974816027fd0ec9d5b5a6acc9c7a1bd7f5769ccc01b7 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-Br):[c:4]:[c;H0;D3;+0:5](-[O;H0;D2;+0:6]-C-c2:c:c:c(-O-C):c:c:2):[cH;D2;+0:7]:1.Br-[c;H0;D3;+0:8]1:[c:9]:[c:10](-[O;H0;D2;+0:11]-C-c2:c:c:c(-O-C):c:c:2):[c:12]:[c:13](-[C:14]=[O;D1;H0:15]):[c:16]:1.[CH3;D1;+0:17]-[c:18](:[c:19]):[#7;a:20]:[c:21].C-c1:c:c:[c;H0;D3;+0:22](-[C;H0;D... | 90 | [{"value": 90.0, "product": "OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC(=CC1)CO", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | [3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-(6-methyl-pyridin-3-yl)-methanone. A 1.6 M solution of n-BuLi in hexane (1.8 mmol) was added dropwise to a stirred mixture of 1,3-dibromo-5-(4-methoxy-benzyloxy)-benzene (600 mg, 1.6 mmol) in dry ether (6 mL) at −78° C. The resulting solution was stirred at −78° C. for 30 min, a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Ether.Ether.Ether.Nitrile | Primary alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | CCOCC | -78 | 0.5 | COc1ccc(COc2cc(Br)cc(Br)c2)cc1.COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(C)nc3)c2)cc1.Cc1ccc(C#N)cn1>CCOCC>O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7737219f4cf3499a853cb7b39ec051ff | COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(COC(C)=O)nc3)c2)cc1.Cc1ccc(C=O)cn1.O=C(OO)c1cccc(Cl)c1>>O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | BrC=1C=C(C(=O)C=2C=CC(=NC2)COC(C)=O)C=C(C1)OCC1=CC=C(C=C1)OC.CC1=CC=C(C=N1)C=O.C1=CC(=CC(=C1)Cl)C(=O)OO>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC(=CC1)CO | COc1ccc(C[O:14][c:13]2[cH:12][c:11]([C:2](=[O:1])[c:3]3[cH:4][cH:5][c:6]([CH2:7][O:8]C(C)=O)[n:9][cH:10]3)[cH:26][c:16](Br)[cH:15]2)cc1.O=[CH:17][c:25]1[cH:18][cH:19][c:23]([CH3:24])[n:22][cH:21]1.O=C(OO)c1cc[cH:20]c(Cl)c1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[n:9][cH:10]1)[c:11]1[cH:12][c:13]([OH:14])[cH... | COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(COC(C)=O)nc3)c2)cc1.Cc1ccc(C=O)cn1.O=C(OO)c1cccc(Cl)c1 | O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6c8da7ce53fd214ec8dfdab510ef17349306a976a4d3fba782d9e9ab63e3685e | fec724f070bb48acdefa813f4b238dca765a2561241e4f3d05461059818d7190 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[O;H0;D2;+0:4]-C-c2:c:c:c(-O-C):c:c:2):[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9]:1.C-C(=O)-[O;H0;D2;+0:10]-[C:11]-[c:12]:[#7;a:13].Cl-c1:[cH;D2;+0:14]:c:c:c(-C(=O)-O-O):c:1.O=[CH;D2;+0:15]-[c;H0;D3;+0:16]1:[cH;D2;+0:17]:[cH;D2;+0:18]:[c;H0;D3;+0:19](-[CH3;D1;+0:20]):[n;H0;D2;+0:21]:[cH;D2;+0... | 31 | [{"value": 31.0, "product": "OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC(=CC1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Acetic acid 5-[3-bromo-5-(4-methoxy-benzyloxy)-benzoyl]-pyridin-2-ylmethyl ester. To a stirred solution of 3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-(6-methyl-pyridin-3-yl)-methanone (388 mg, 0.94 mmol) in dry methylene chloride (20 mL) at 0° C. was added dropwise a solution of MCPBA (0.371 mg, 1.50 mmol) in methylene ch... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aldehyde.Ester.Ether.Ether.Peroxide | Primary alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccncc1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HCl.Br- | C(Cl)Cl | null | 8 | COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(COC(C)=O)nc3)c2)cc1.Cc1ccc(C=O)cn1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6703728128714fcc8e5ef29e680462c9 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(COC(C)=O)nc3)c2)cc1>>O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].BrC=1C=C(C(=O)C=2C=CC(=NC2)COC(C)=O)C=C(C1)OCC1=CC=C(C=C1)OC.COC1=CC=C(COC=2C=C(C(=O)C=3C=CC(=NC3)COC(C)=O)C=C(C2)C2=C3C=CN(C3=CC=C2)[Si](C(C)C)(C(C)C)C(C)C)C=C1.CC1(OB(OC1(C)C)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC(=CC1)CO | CC(C)[Si](C(C)C)(C(C)C)[n:22]1[c:21]2[cH:20][cH:19][cH:18][c:17](B3OC(C)(C)C(C)(C)O3)[c:25]2[cH:24][cH:23]1.COc1ccc(C[O:14][c:13]2[cH:12][c:11]([C:2](=[O:1])[c:3]3[cH:4][cH:5][c:6]([CH2:7][O:8]C(C)=O)[n:9][cH:10]3)[cH:26][c:16](Br)[cH:15]2)cc1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[n:9][cH:10]1)[c:11]1[cH:... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(COC(C)=O)nc3)c2)cc1 | O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | null | Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1 | O1CCOCC1.C(Cl)Cl | C-C Coupling | OtherReaction | 03c0602d335cce017caa249dd9f408403bceda0791224bef598f481caa20bd25 | 2623277bd6e5f54360592f40b6a823951456d639d0d506a8c2827cddd3033ea0 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[O;H0;D2;+0:4]-C-c2:c:c:c(-O-C):c:c:2):[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9]:1.C-C(=O)-[O;H0;D2;+0:10]-[C:11]-[c:12]:[#7;a:13].C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]2:[c:18]:1:[c:19]:[c:20]:[c:21]:[c;H0;D3;+0:22]:2-B1-O-C(-C)(-C)-C(-C)(-C)-O-1>>[#7;a:13]:[... | null | [] | null | null | null | null | Acetic acid 5-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-benzoyl]-pyridin-2-ylmethyl ester. To the mixture of acetic acid 5-[3-bromo-5-(4-methoxy-benzyloxy)-benzoyl]-pyridin-2-ylmethyl ester (145 mg, 0.308 mmol) and chloro(di-2-norbornylphosphino)(2′dimethylamino-1,1′-biphenyl-2-yl)palladium (II) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ether.Ether.Boronic ester.Silyl protective group | Primary alcohol.Aromatic alcohol | c1cccc2[nH]ccc12.B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HBr.B | Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1.O1CCOCC1.C(Cl)Cl | null | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(COC(C)=O)nc3)c2)cc1>Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1.O1CCOCC1.C(Cl)Cl>O=C(c1ccc(CO)nc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee78f4f15c7742d89b86ba8906c4996d | CC(C)[Si](Oc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1)(C(C)C)C(C)C>>CC(O)(c1cccnc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | CCCC[N+](CCCC)(CCCC)CCCC.[F-].N1=CC(=CC=C1)C(=O)C1=CC(=CC(=C1)O[Si](C(C)C)(C(C)C)C(C)C)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C.C[Mg]Cl>>OC(C)(C=1C=NC=CC1)C=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)O | CC(C)[Si](C(C)C)(C(C)C)[O:13][c:12]1[cH:11][c:10]([C:2](=[O:3])[c:4]2[cH:5][cH:6][cH:7][n:8][cH:9]2)[cH:25][c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]3[n:21]([Si](C(C)C)(C(C)C)C(C)C)[cH:22][cH:23][c:24]23)[cH:14]1>>[CH3:1][C:2]([OH:3])([c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)[c:10]1[cH:11][c:12]([OH:13])[cH:14][c:15](-[c:1... | CC(C)[Si](Oc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1)(C(C)C)C(C)C | CC(O)(c1cccnc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 | null | null | [Cl-].[Na+].O.C1CCOC1 | Miscellaneous | OtherReaction | 7ca7083e374d5c1bb0751ac24fce95f1cc0a06ac813068111afddc4fa2035727 | 1006a427946ab05af95065220492931e2df745bcea703fed167e9a72cf9ce48d | c1cncc(Cc2cccc(-c3cccc4[nH]ccc34)c2)c1 | C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6].C-C(-C)-[Si](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]:[c:11](-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[c:14](:[c:15]):[c:16]:[#7;a:17]:[c:18]):[c:19])(-C(-C)-C)-C(-C)-C>>[C;D1;H3:20]-[C;H0;D4;+0:12](-[OH;D1;+0:13])(-[c:11](:[c:19]):[c:10]:[c:8](-[OH... | 39 | [{"value": 39.0, "product": "OC(C)(C=1C=NC=CC1)C=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To pyridin-3-yl-[3-(1-triisopropylsilanyl-1H-indol-4-yl)-5-triisopropylsilanyloxy-phenyl]-methanone (64 mg, 0.102 mmol) in 2 mL of THF was added 2 mL of MeMgCl (1 M in THF) at 0° C. After 30 min TLC indicated the completion of the reaction. Brine was then added to quench the reaction. The aqueous phase was then extract... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Silyl protective group.Silyl protective group | Tertiary alcohol.Aromatic alcohol | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | Other | [Cl-].[Na+].O.C1CCOC1 | null | 0.5 | CC(C)[Si](Oc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1)(C(C)C)C(C)C>[Cl-].[Na+].O.C1CCOC1>CC(O)(c1cccnc1)c1cc(O)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1503960581b64c7bacfc5d703c708315 | CC(C)(C)[Si](C)(C)Oc1ccc(C(O)c2cccnc2)cc1C12CC3CC(CC(C3)C1)C2>>CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)c2cccnc2)cc1C12CC3CC(CC(C3)C1)C2 | C12(CC3CC(CC(C1)C3)C2)C=2C=C(C=CC2O[Si](C)(C)C(C)(C)C)C(O)C=2C=NC=CC2.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>C12(CC3CC(CC(C1)C3)C2)C=2C=C(C=CC2O[Si](C)(C)C(C)(C)C)C(=O)C=2C=NC=CC2 | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([CH:13]([OH:14])[c:15]2[cH:16][cH:17][cH:18][n:19][cH:20]2)[cH:21][c:22]1[C:23]12[CH2:24][CH:25]3[CH2:26][CH:27]([CH2:28][CH:29]([CH2:30]3)[CH2:31]1)[CH2:32]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][c... | CC(C)(C)[Si](C)(C)Oc1ccc(C(O)c2cccnc2)cc1C12CC3CC(CC(C3)C1)C2 | CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)c2cccnc2)cc1C12CC3CC(CC(C3)C1)C2 | null | null | CCOCC.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1cccnc1)c1cccc(C23CC4CC(CC(C4)C2)C3)c1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | null | [] | null | null | 10 | MINUTE | [3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-pyridin-3-yl-methanol (55 mg, 0.112 mmol) was dissolved in methylene chloride. The Dess Martin periodane (0.104 g, 0.224 mmol) was then added to the reaction mixture. The reaction was complete within 10 min and was then diluted with ether. The organic layer w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccncc1.C1C2CC3CC1CC(C2)C3 | null | CCOCC.C(Cl)Cl | null | 0.166667 | CC(C)(C)[Si](C)(C)Oc1ccc(C(O)c2cccnc2)cc1C12CC3CC(CC(C3)C1)C2>CCOCC.C(Cl)Cl>CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)c2cccnc2)cc1C12CC3CC(CC(C3)C1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55a5b51c94a14dc0bcea4aac4ff00ba7 | COC(=O)c1cc(Br)cc(Br)c1.Nc1cccnc1>>COC(=O)c1cc(Br)cc(Nc2cccnc2)c1 | COC(C1=CC(=CC(=C1)Br)Br)=O.N1=CC(=CC=C1)N.COC(C1=CC(=CC(=C1)NC=1C=NC=CC1)C1=C2C=CNC2=CC=C1)=O>>COC(C1=CC(=CC(=C1)NC=1C=NC=CC1)Br)=O | 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][n: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][n:16][cH:17]2)[cH:18]1 | COC(=O)c1cc(Br)cc(Br)c1.Nc1cccnc1 | COC(=O)c1cc(Br)cc(Nc2cccnc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)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]:[#7;a:13]:[c:14]>>[#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]:[#7;a:13]:[c:14]):[c:7]:[c:8] | null | [] | null | null | null | null | 3-Bromo-5-(pyridin-3-ylamino)-benzoic acid methyl ester was prepared from 3,5-dibromo-benzoic acid methyl ester and pyridin-3-ylamine in low yield as described for Example 36, except that the reaction was run at 130° C. This material was converted to 3-(1H-indol-4-yl)-5-(pyridin-3-ylamino)-benzoic acid methyl ester by ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HBr | null | null | null | COC(=O)c1cc(Br)cc(Br)c1.Nc1cccnc1>>COC(=O)c1cc(Br)cc(Nc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d0e740c926b47bd93f066dc842f030c | N#Cc1cc(Br)cc(Br)c1.Nc1cccnc1>>N#Cc1cc(Br)cc(Nc2cccnc2)c1 | BrC=1C=C(C#N)C=C(C1)Br.N1=CC(=CC=C1)N.N1C=CC2=C(C=CC=C12)C=1C=C(C#N)C=C(C1)NC=1C=NC=CC1>>BrC=1C=C(C#N)C=C(C1)NC=1C=NC=CC1 | Br[c:8]1[cH:7][c:5]([Br:6])[cH:4][c:3]([C:2]#[N:1])[cH:16]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[cH:16]1 | N#Cc1cc(Br)cc(Br)c1.Nc1cccnc1 | N#Cc1cc(Br)cc(Nc2cccnc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[#7;a:10]:[c:11] | null | [] | null | null | null | null | 3-Bromo-5-(pyridin-3-ylamino)-benzonitrile was prepared from 3,5-dibromobenzonitrile and pyridin-3-ylamine as described for Example 36, except that the reaction was run at 130° C. This material was converted to 3-(1H-indol-4-yl)-5-(pyridin-3-ylamino)-benzonitrile by the method of Example 35. 1H NMR (400 MHz, CDCl3): δ ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HBr | null | null | null | N#Cc1cc(Br)cc(Br)c1.Nc1cccnc1>>N#Cc1cc(Br)cc(Nc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dae9a6a9077749918dfd61060c9a2cdb | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1>>Oc1cc(Br)cc(Nc2cccnc2)c1 | BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)NC=1C=NC=CC1.C1(=CC=CC=C1)SC.FC(C(=O)O)(F)F>>BrC=1C=C(C=C(C1)NC=1C=NC=CC1)O | COc1ccc(C[O:1][c:2]2[cH:3][c:4]([Br:5])[cH:6][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][n:13][cH:14]3)[cH:15]2)cc1>>[OH:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[cH:15]1 | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1 | Oc1cc(Br)cc(Nc2cccnc2)c1 | null | null | O | Reduction | OtherReaction | 8a4606e79840bb3d9b3a2e0b7d9ed5648d76ae6cbcc894506db9722ac2624f9a | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1ccc(Nc2cccnc2)cc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):c:c:1>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 50.2 | [{"value": 50.0, "product": "BrC=1C=C(C=C(C1)NC=1C=NC=CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "BrC=1C=C(C=C(C1)NC=1C=NC=CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 100 | MINUTE | [3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine (26.7 g, 69.2 mmol) was dissolved in thioanisole (62 mL, 529 mmol). Trifluoroacetic acid (81 mL, 1.06 mol) was added slowly with the temperature held between 20 and 25° C. over a period of 100 min. The solution was left to stand at room temperature for 2 hours... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccncc1 | HO- | O | null | 1.666667 | COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1>O>Oc1cc(Br)cc(Nc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c98fbd1f4a384f9ea983660d178fffc7 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.Oc1cc(Br)cc(Nc2cccnc2)c1>>CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1 | BrC=1C=C(C=C(C1)NC=1C=NC=CC1)O.[H-].[Na+].[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)Cl>>BrC=1C=C(C=C(C1)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)NC=1C=NC=CC1 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1.[OH:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([NH... | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.Oc1cc(Br)cc(Nc2cccnc2)c1 | CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1 | null | null | C(C)(C)(C)OC.CN(C)C=O | Protection | Alcohol protection with silyl ethers | b0a79881d208ba0e98fadf827b99c8e154abae20183442d92687b20dcffdaf4c | d57b05ecffa00e68e6b49fce42d0b589b6267b94f85326e13293a0e3abd8a48b | c1ccc([SiH](Oc2cccc(Nc3cccnc3)c2)c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[Si;H0;D4;+0:1](-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15])(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7] | 96.1 | [{"value": 96.0, "product": "BrC=1C=C(C=C(C1)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)NC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "BrC=1C=C(C=C(C1)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)NC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | 3-Bromo-5-(pyridin-3-ylamino)-phenol (11.62 g, 43.83 mmol) was dissolved in DMF (115 mL) under dry argon and cooled to 0° C. Then 60% NaH (1.93 g, 48.21 mmol) was added in small portions over a period of 45 min. Stirring was continued for 15 min, followed by drop wise addition of TBDPS-chloride (11.2 mL, 43.83 mmol). T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | Silyl protective group | null | null | c1ccccc1.c1ccncc1.c1ccccc1.c1ccccc1 | HCl | C(C)(C)(C)OC.CN(C)C=O | 0 | 0.25 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.Oc1cc(Br)cc(Nc2cccnc2)c1>C(C)(C)(C)OC.CN(C)C=O>CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad593bde0fd14ee0b8927e3856b5335d | COc1cc(Br)cc(Br)c1.ClI>>COc1cc(Br)cc(I)c1 | BrC1=CC(=CC(=C1)OC)Br.ICl.C(CCC)[Mg]Cl.C(CCC)[Li].CCCCCC>>BrC1=CC(=CC(=C1)OC)I | Br[c:8]1[cH:7][c:5]([Br:6])[cH:4][c:3]([O:2][CH3:1])[cH:10]1.Cl[I:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([I:9])[cH:10]1 | COc1cc(Br)cc(Br)c1.ClI | COc1cc(Br)cc(I)c1 | null | null | O.C1(=CC=CC=C1)C.C(Cl)Cl | Functional Group Interconversion | OtherReaction | b78ae091f9ea90a571f2e011b77da2eac9952c7b340e2e0185fb0decffadd167 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Cl-[I;H0;D1;+0:6]>>[I;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 60 | [{"value": 60.0, "product": "BrC1=CC(=CC(=C1)OC)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "BrC1=CC(=CC(=C1)OC)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 15 | MINUTE | A 1.6 M solution of n-butyllithium in hexane (5.65 mL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to −5° C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL, 4.52 mmol) was added slowly with the temperature held below 0° C. over a period of 15 min. Stirring was continued for 45 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | O.C1(=CC=CC=C1)C.C(Cl)Cl | -5 | 0.25 | COc1cc(Br)cc(Br)c1.ClI>O.C1(=CC=CC=C1)C.C(Cl)Cl>COc1cc(Br)cc(I)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c82d30573024422aae1fd2c8d0f47fec | COc1cc(Br)cc(I)c1>>Oc1cc(Br)cc(I)c1 | BrC1=CC(=CC(=C1)OC)I.Br>>BrC=1C=C(C=C(C1)I)O | C[O:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([I:8])[cH:9]1>>[OH:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([I:8])[cH:9]1 | COc1cc(Br)cc(I)c1 | Oc1cc(Br)cc(I)c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)(=O)O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 352.9 | [{"value": 96.0, "product": "BrC=1C=C(C=C(C1)I)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 352.9, "product": "BrC=1C=C(C=C(C1)I)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | 1-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33%, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)O | null | 48 | COc1cc(Br)cc(I)c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)O>Oc1cc(Br)cc(I)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5c30b34a447446bb1f71cc9561ce8c5 | COc1ccc(CCl)cc1.Oc1cc(Br)cc(I)c1>>COc1ccc(COc2cc(Br)cc(I)c2)cc1 | BrC=1C=C(C=C(C1)I)O.C([O-])([O-])=O.[K+].[K+].COC1=CC=C(CCl)C=C1>>BrC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)I | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]1.[OH:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][c:14]([I:15])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([I:15])[cH:16]2)[cH:17][cH:18]1 | COc1ccc(CCl)cc1.Oc1cc(Br)cc(I)c1 | COc1ccc(COc2cc(Br)cc(I)c2)cc1 | null | COC1=CC=C(CCl)C=C1 | O.C(C)(C)(C)OC.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 77.8 | [{"value": 59.0, "product": "BrC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "BrC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | HOUR | 3-Bromo-5-iodo-phenol (8.48 g, 28.37 mmol) was dissolved in DMF (50 mL) under dry argon and cooled to 0° C. Then potassium carbonate (3.92 g, 28.37 mmol) was added, followed by drop wise addition of 4-methoxybenzyl chloride (3.7 mL, 27.0 mmol). The mixture was slowly warmed to room temperature and stirred for 20 h. Add... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | COC1=CC=C(CCl)C=C1.O.C(C)(C)(C)OC.CN(C)C=O | 0 | 20 | COc1ccc(CCl)cc1.Oc1cc(Br)cc(I)c1>COC1=CC=C(CCl)C=C1.O.C(C)(C)(C)OC.CN(C)C=O>COc1ccc(COc2cc(Br)cc(I)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-248392b0c6ba4032a2242aa879019276 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(I)c2)cc1>>COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | C([O-])([O-])=O.[Na+].[Na+].CCOC(=O)C.CC1(OB(OC1(C)C)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C.BrC1=CC(=CC(=C1)OCC1=CC=C(C=C1)OC)I>>BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C | CC1(C)OB([c:15]2[cH:16][cH:17][cH:18][c:19]3[c:20]2[cH:21][cH:22][n:23]3[Si:24]([CH:25]([CH3:26])[CH3:27])([CH:28]([CH3:29])[CH3:30])[CH:31]([CH3:32])[CH3:33])OC1(C)C.I[c:14]1[cH:13][c:11]([Br:12])[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]2)[cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(I)c2)cc1 | COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | null | null | O.C1(=CC=CC=C1)C.[Cl-].[Na+].O.C(C)O | C-C Coupling | Suzuki coupling with boronic esters | 249e9ec88fe1f875d28a2bdea7312c498c739ad3410a41394c8450f214b938e7 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(COc2cccc(-c3cccc4[nH]ccc34)c2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[c:5]3:[#7;a:6](-[#14:7](-[C:8])(-[C:9])-[C:10]):[c:11]:[c:12]:[c:13]:3:2)-O-C-1(-C)-C.I-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[C:8]-[#14:7](-[C:9])(-[C:10])-[#7;a:6]1:[c:11]:[c:12]:[c:13]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[c;H0;D3;+0:14](:[c:15]:[c:16]... | 91.3 | [{"value": 91.0, "product": "BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 90 | CELSIUS | 14 | HOUR | A 1 L flask was charged with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (17.44 g, 43.67 mmol) and 1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene (18.30 g, 43.67 mmol) in ethanol (180 mL) and toluene (180 mL) under argon. Tetrakis-triphenylphosphin-palladium (1.51 g, 1.31 mmol) was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1cccc2[nH]ccc12.c1ccccc1 | c1ccccc1.c1cccc2[nH]ccc12 | c1ccccc1.c1ccccc1.c1cccc2[nH]ccc12 | HI.B | O.C1(=CC=CC=C1)C.[Cl-].[Na+].O.C(C)O | 90 | 14 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COc1ccc(COc2cc(Br)cc(I)c2)cc1>O.C1(=CC=CC=C1)C.[Cl-].[Na+].O.C(C)O>COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 |
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