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-2b65fbb62b1847dba2e7c16757c6dac1 | COc1ccc(COc2cc(Br)cc(C(O)c3ccc(OC)nc3)c2)cc1>>COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(OC)nc3)c2)cc1 | C(=O)(O)[O-].[Na+].[O-]S(=O)(=S)[O-].[Na+].[Na+].BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)C(O)C=1C=NC(=CC1)OC.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>BrC=1C=C(C=C(C1)OCC1=CC=C(C=C1)OC)C(=O)C=1C=NC(=CC1)OC | [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]([CH:15]([OH:16])[c:17]3[cH:18][cH:19][c:20]([O:21][CH3:22])[n:23][cH:24]3)[cH:25]2)[cH:26][cH:27]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]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:2... | COc1ccc(COc2cc(Br)cc(C(O)c3ccc(OC)nc3)c2)cc1 | COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(OC)nc3)c2)cc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1cccnc1)c1cccc(OCc2ccccc2)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 | 1 | HOUR | To [3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-(6-methoxy-pyridin-3-yl)-methanol in methylene chloride (5 mL) at room temperature was added Dess-Martin reagent. The resulting reaction mixture was stirred at room temperature for 1 h. Sat. NaHCO3 and Na2S2O3 were then added and the stirring was continued until both phases b... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | null | C(Cl)Cl | null | 1 | COc1ccc(COc2cc(Br)cc(C(O)c3ccc(OC)nc3)c2)cc1>C(Cl)Cl>COc1ccc(COc2cc(Br)cc(C(=O)c3ccc(OC)nc3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf7c1aa2d4904ff2b4fe22d102d65b39 | COc1ccc(COc2cc(C(=O)c3ccc(OC)nc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1>>COc1ccc(C(=O)c2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 | C(=O)(O)[O-].[Na+].CCOC(=O)C.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)OC)C=C1.B(F)(F)F>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC(=CC1)OC | COc1ccc(C[O:12][c:11]2[cH:10][c:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[n:26][cH:25]3)=[O:8])[cH:24][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]4[n:20]([Si](C(C)C)(C(C)C)C(C)C)[cH:21][cH:22][c:23]34)[cH:13]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([OH:12])[cH:13][c:14](-[c:15]3[cH... | COc1ccc(COc2cc(C(=O)c3ccc(OC)nc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | COc1ccc(C(=O)c2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 | null | null | CSC | Reduction | OtherReaction | 63dde71090524dfe816aacbeb73220ede8c80fc03e995eb7b05c27dc4b663a4a | e0b1422bef25db45aecd1b91d52276549faecdaa4ba19e30ce4bb80cad333481 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)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-O-c1:c:c:c(-C-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):c:c:1>>[OH;D1;+0:7]-[c:8](:[c:9]):[c:10].[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 75 | [{"value": 75.0, "product": "OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC(=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | To compound [3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-(6-methoxy-pyridin-3-yl)-methanone in dimethylsulfide (2 mL) at 0° C. was added excess BF3 etherate. The resulting reaction mixture was stirred at 0° C. for 20 min. TLC indicated that the disappearance of the starting material. EtOAc w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group | Aromatic alcohol | c1ccccc1.c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | CSC | 0 | 0.333333 | COc1ccc(COc2cc(C(=O)c3ccc(OC)nc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1>CSC>COc1ccc(C(=O)c2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dfa17ba556264a328dac0eea9f63cc8c | Brc1cc(Br)cc(Br)c1.N#Cc1cccnc1>>O=C(c1cccnc1)c1cc(Br)cc(Br)c1 | BrC1=CC(=CC(=C1)Br)Br.[Li]CCCC.C(#N)C=1C=NC=CC1.C(C)OCC>>BrC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1 | Br[c:9]1[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]1.N#[C:2][c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]1 | Brc1cc(Br)cc(Br)c1.N#Cc1cccnc1 | O=C(c1cccnc1)c1cc(Br)cc(Br)c1 | null | null | null | Functional Group Interconversion | Grignard_carbonyl | f86e5c540ffe2d1de473163d2ef84d901e1d7375c2ef2d60d33c57a185e6e160 | eeadf1d87b57f63c0bbfdb5c9b6e16f4d991a73b3dda84409796ea51d7226f3a | O=C(c1ccccc1)c1cccnc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].N#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[O;D1;H0:12]=[C;H0;D3;+0:6](-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 81 | [{"value": 81.0, "product": "BrC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | -72 | CELSIUS | 30 | MINUTE | 1,3,5-Tribromo-benzene (31.4 g, 100 mmol) was dissolved under argon in a flame dried three-neck flask in 1000 mL diethylether and the solution was cooled to −72° C. A solution of 62 mL nBuLi (1.6 M in hexane, 100 mmol) was added to the resulting suspension in such a fashion that temperature did not rise above −70° C. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitrile | Ketone | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | Br- | null | -72 | 0.5 | Brc1cc(Br)cc(Br)c1.N#Cc1cccnc1>>O=C(c1cccnc1)c1cc(Br)cc(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ab94aa7f7d849508f04b6631b696316 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NC(=O)OCc4ccccc4)cc(C(=O)c4cccnc4)c3)cccc21>>O=C(Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N)=O.C(C1=CC=CC=C1)OC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C=1C=NC=CC1)=O>>C(C1=CC=CC=C1)OC(NC1=CC(=CC(=C1)C(=O)C=1C=NC=CC1)C1=C2C=CNC2=CC=C1)=O | CC(C)[Si](C(C)C)(C(C)C)[n:22]1[c:21]2[cH:20][cH:19][cH:18][c:17](-[c:16]3[cH:15][c:6]([C:7](=[O:8])[c:9]4[cH:10][cH:11][cH:12][n:13][cH:14]4)[cH:5][c:4]([NH:3][C:2](=[O:1])[O:27][CH2:28][c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[cH:26]3)[c:25]2[cH:24][cH:23]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[c:9]2[c... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NC(=O)OCc4ccccc4)cc(C(=O)c4cccnc4)c3)cccc21 | O=C(Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1)OCc1ccccc1 | null | null | null | Deprotection | OtherReaction | 7c2e21594486284c07d91d3a35172f6f97c1f0e21d7ef6570d737987b23577df | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | O=C(Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1)OCc1ccccc1 | 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 | null | [] | null | null | null | null | 3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid benzyl ester was converted to [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid benzyl ester, then deprotected to give [3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid benzyl ester by the method of Example 35. 1H ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | null | null | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NC(=O)OCc4ccccc4)cc(C(=O)c4cccnc4)c3)cccc21>>O=C(Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f5a2e78bb4c4125b24dc9e4ed5f1b33 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NC(=O)OCc4ccccc4)cc(C(=O)c4cccnc4)c3)cccc21>>Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | C(C1=CC=CC=C1)OC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C=1C=NC=CC1)=O>>NC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC=CC1 | 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]([C:5](=[O:6])[c:7]4[cH:8][cH:9][cH:10][n:11][cH:12]4)[cH:3][c:2]([NH:1]C(=O)OCc4ccccc4)[cH:24]3)[c:23]2[cH:22][cH:21]1>>[NH2:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[cH:13][c:14](-[c:15]2[cH:16][cH:17]... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NC(=O)OCc4ccccc4)cc(C(=O)c4cccnc4)c3)cccc21 | Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | null | null | O.[OH-].[K+].CO.O | Reduction | OtherReaction | 746c2bcb0c001d8e545af55a442bec2c71e793bb115896ae6f2069eaa6f0bc43 | cf44df1d2dd370043a24817754a3894c0fe86e4e933200e5117f668744ac83b8 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)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].O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10].[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 57.5 | [{"value": 57.0, "product": "NC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "NC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | [3-(Pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid benzyl ester (40 mg, 0.066 mmol) in 40% KOH in MeOH/H2O (5 mL/5 mL) was brought to reflux for 2 hours. After cooling down to room temperature, the mixture was diluted with water, and extracted with EtOAc. The organic layers were sepa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Silyl protective group | Primary amine | c1cccc2[nH]ccc12.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HO- | O.[OH-].[K+].CO.O | null | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NC(=O)OCc4ccccc4)cc(C(=O)c4cccnc4)c3)cccc21>O.[OH-].[K+].CO.O>Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b15b8fa88a84ff08653dbd6ba33a023 | CC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>>CC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | O.NC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1.C(C)(C)N(CC)C(C)C.C(C)(=O)Cl>>BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NC(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][n:17][cH:18]2)[cH:19]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][n:17][cH:18]2)[cH:19]1 | CC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | CC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | null | null | ClC(C)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)c1cccnc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 10 | MINUTE | To 0.2 g of (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone in 10 mL of dichloroethane was added 0.126 mL of diisopropyl ethyl amine and 0.051 mL of acetyl chloride. The reaction mixture was stirred for 10 minutes then poured into water and extracted twice with CH2Cl2. The organic phase was dried over sodium sulfate, f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | ClC(C)Cl | null | 0.166667 | CC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>ClC(C)Cl>CC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48100cc199564a2dbe594161ff885133 | CC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>CC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NC(C)=O.N1=CC(=CC=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC(C)=O>>N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NC(C)=O | CC(C)[Si](C(C)C)(C(C)C)[n:23]1[c:22]2[cH:21][cH:20][cH:19][c:18](-[c:17]3[cH:16][c:7]([C:8](=[O:9])[c:10]4[cH:11][cH:12][cH:13][n:14][cH:15]4)[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:27]3)[c:26]2[cH:25][cH:24]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[cH:16... | CC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | CC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | null | null | null | Deprotection | OtherReaction | 7c2e21594486284c07d91d3a35172f6f97c1f0e21d7ef6570d737987b23577df | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)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 | null | [] | null | null | null | null | N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-acetamide was converted to N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide, and the triisopropylsilyl group was removed with tetra n-butylammonium fluoride to give N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-acetamide as described ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>CC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd11fe7677f4464a8695a136604a45f5 | CS(=O)(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>>CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | CS(=O)(=O)Cl.NC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1.N1=CC=CC=C1>>BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:20]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:20]1 | CS(=O)(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | null | null | ClC(C)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(c1ccccc1)c1cccnc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 58.7 | [{"value": 58.7, "product": "BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To a stirred solution of 0.200 grams of (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.72 mmol) in 10 mL of dichloroethane was added 0.87 mL (10.82 mmol) of pyridine followed by the addition of 0.56 mL (7.2 mmol) of methanesulfonyl chloride. The reaction was stirred at 80° C. for 2 hours. The volatiles were removed... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccncc1 | HCl | ClC(C)Cl | 80 | 2 | CS(=O)(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>ClC(C)Cl>CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71213a03d6714097ba2c1921778420ef | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NS(C)(=O)=O)cc(C(=O)c4cccnc4)c3)cccc21.CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1>>CS(=O)(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NS(=O)(=O)C.N1=CC(=CC=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NS(=O)(=O)C>>N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NS(=O)(=O)C | CC(C)[Si](C(C)C)(C(C)C)[n:24]1[c:23]2[cH:22][cH:21][cH:20][c:19](-[c:18]3cc(NS(C)(=O)=O)c[c:8]([C:9](=[O:10])[c:11]4[cH:12][cH:13][cH:14][n:15][cH:16]4)[cH:17]3)[c:27]2[cH:26][cH:25]1.O=C(c1cccnc1)c1cc(Br)[cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:28]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([C:9](... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NS(C)(=O)=O)cc(C(=O)c4cccnc4)c3)cccc21.CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | CS(=O)(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | null | null | null | Miscellaneous | OtherReaction | 57b8339ae8f08bc467fd1435ecaab06e79034d473a00c998cf5486a74e753dd9 | 896b660a3dd2123ddaf2a9eb82356e7d6d2e2a3e758fb3c90df51994b3e35010 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-c1:[cH;D2;+0:1]:[c:2](-[#7:3]):[cH;D2;+0:4]:c(-C(=O)-c2:c:c:c:n:c:2):c:1.C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8](:[c:9](-[c;H0;D3;+0:10]2:[c:11]:[c;H0;D3;+0:12](-[C:13](=[O;D1;H0:14])-[c:15]:[c:16]:[#7;a:17]):c:c(-N-S(-C)(=O)=O):c:2):[c:18]):[c:19]:1:[c:20]>>[#7:3]-[c:2]1:[cH;D2;+0:4]:[c;H... | null | [] | null | null | null | null | N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-methanesulfonamide was converted to N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-methanesulfonamide, and the triisopropylsilyl group was removed with tetra n-butylammonium fluoride to give N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-metha... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide.Ketone.Ketone.Silyl protective group | Ketone | c1cccc2[nH]ccc12.c1ccccc1.c1ccncc1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HBr | null | null | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(-c3cc(NS(C)(=O)=O)cc(C(=O)c4cccnc4)c3)cccc21.CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1>>CS(=O)(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e49b47b5d77249859658952d70194642 | COC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>>COC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | NC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1.N1=CC=CC=C1.COC(=O)Cl>>COC(NC1=CC(=CC(=C1)C(=O)C=1C=NC=CC1)Br)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:20]1 | COC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | COC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | null | null | ClCCl.ClC(C)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(c1ccccc1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 86 | [{"value": 86.0, "product": "COC(NC1=CC(=CC(=C1)C(=O)C=1C=NC=CC1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a stirred solution of 0.20 g of (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.72 mmol) in 5 mL of dichloroethane was added 0.58 mL of pyridine and 0.55 mL of methylchloroformate, and the mixture was heated to 60° C. for 20 minutes. The reaction was diluted with dichloromethane and washed with saturated aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccncc1 | HCl | ClCCl.ClC(C)Cl | 60 | null | COC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>ClCCl.ClC(C)Cl>COC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44a512c93d614393a6546052294ee94c | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1>>COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | COC(NC1=CC(=CC(=C1)C(=O)C=1C=NC=CC1)Br)=O.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+]>>COC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C=1C=NC=CC1)=O | CC1(C)OB([c:19]2[cH:20][cH:21][cH:22][c:23]3[c:24]2[cH:25][cH:26][n:27]3[Si:28]([CH:29]([CH3:30])[CH3:31])([CH:32]([CH3:33])[CH3:34])[CH:35]([CH3:36])[CH3:37])OC1(C)C.Br[c:18]1[cH:17][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:38]1>>[CH3:1][O:2][C:3](=[... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)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-C Coupling | Suzuki coupling with boronic esters | 249e9ec88fe1f875d28a2bdea7312c498c739ad3410a41394c8450f214b938e7 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].C-C1(-C)-O-B(-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[c:12]3:[#7;a:13](-[#14:14](-[C:15])(-[C:16])-[C:17]):[c:18]:[c:19]:[c:20]:3:2)-O-C-1(-C)-C>>[C:15]-[#14:14](-[C:16])(-[C:17])-[#7;a:13]1:[c:18]:[c:19]:[c:20]2:[c:12]:1:[c:11]:[c:10]:[c:9]:[c;H0;D3;+0:8]:2-[c... | 70.6 | [{"value": 70.0, "product": "COC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C=1C=NC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "COC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C=1C=NC=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | [3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester (316 mg, 0.94 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (0.377 mg, 0.94 mmol) and chloro(di-2-norbornylphosphino)(2′dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (53 mg, 0.094 mmol) were dissolved in diox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1cccc2[nH]ccc12.c1ccccc1 | c1ccccc1.c1cccc2[nH]ccc12 | c1ccccc1.c1ccncc1.c1cccc2[nH]ccc12 | 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 | null | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.COC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1>Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1.O1CCOCC1>COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3bd3a8925f5747e98eebb13938d740d2 | COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | COC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C=1C=NC=CC1)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C(C)(=O)OCC>>COC(NC1=CC(=CC(=C1)C(=O)C=1C=NC=CC1)C1=C2C=CNC2=CC=C1)=O | CC(C)[Si](C(C)C)(C(C)C)[n:24]1[c:23]2[cH:22][cH:21][cH:20][c:19](-[c:18]3[cH:17][c:8]([C:9](=[O:10])[c:11]4[cH:12][cH:13][cH:14][n:15][cH:16]4)[cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:28]3)[c:27]2[cH:26][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][cH... | COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | null | null | C1CCOC1 | Deprotection | OtherReaction | 7c2e21594486284c07d91d3a35172f6f97c1f0e21d7ef6570d737987b23577df | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)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 | null | [] | null | null | 10 | MINUTE | To a stirred solution of 0.160 g (0.31 mmol) of [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester in 5 mL of THF was added 0.310 mL of 1M tetra-n-butylammonium fluoride in THF. The reaction was stirred 10 min, poured into water and ethyl acetate. The phases were separat... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | Other | C1CCOC1 | null | 0.166667 | COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>C1CCOC1>COC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c80f051e3b5148c9a0d49ede2623aee0 | CCC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>>CCC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | C([O-])(O)=O.[Na+].NC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1.C(C)(C)N(CC)C(C)C.C(CC)(=O)Cl>>BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NC(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:20]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[cH:20]1 | CCC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | CCC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | null | null | ClC(C)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 1 | HOUR | To 0.20 g of (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.72 mmol) in 10 mL of dichloroethane was added 0.25 mL of diisopropylethylamine and 0.065 mL of propionyl chloride. The reaction was stirred 1 h at ambient temperature, then poured into saturated aqueous sodium bicarbonate. The phases were separated and the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | ClC(C)Cl | null | 1 | CCC(=O)Cl.Nc1cc(Br)cc(C(=O)c2cccnc2)c1>ClC(C)Cl>CCC(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c072a979a3cd4577b6994bb033b47d10 | CCC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>CCC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NC(CC)=O.N1=CC(=CC=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC(CC)=O>>N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NC(CC)=O | CC(C)[Si](C(C)C)(C(C)C)[n:24]1[c:23]2[cH:22][cH:21][cH:20][c:19](-[c:18]3[cH:17][c:8]([C:9](=[O:10])[c:11]4[cH:12][cH:13][cH:14][n:15][cH:16]4)[cH:7][c:6]([NH:5][C:3]([CH2:2][CH3:1])=[O:4])[cH:28]3)[c:27]2[cH:26][cH:25]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15... | CCC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | CCC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 | null | null | null | Deprotection | OtherReaction | 7c2e21594486284c07d91d3a35172f6f97c1f0e21d7ef6570d737987b23577df | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)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 | null | [] | null | null | null | null | N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-propionamide was converted to N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-propionamide, and the triisopropylsilyl group was removed with tetra n-butylammonium fluoride to give N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-propionamide as d... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CCC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>CCC(=O)Nc1cc(C(=O)c2cccnc2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3547cc7b96ce462eb0b07ee1663ebfe7 | COc1ccc(CCl)cc1.Oc1ccc(Br)cc1Br>>COc1ccc(COc2ccc(Br)cc2Br)cc1 | C([O-])([O-])=O.[Cs+].[Cs+].COC1=CC=C(CCl)C=C1.BrC1=C(C=CC(=C1)Br)O.C([O-])([O-])=O.[K+].[K+]>>BrC1=C(C=CC(=C1)Br)OCC1=CC=C(C=C1)OC | 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][cH:11][c:12]([Br:13])[cH:14][c:15]1[Br:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[Br:16])[cH:17][cH:18]1 | COc1ccc(CCl)cc1.Oc1ccc(Br)cc1Br | COc1ccc(COc2ccc(Br)cc2Br)cc1 | null | null | O.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] | 98 | [{"value": 98.0, "product": "BrC1=C(C=CC(=C1)Br)OCC1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "BrC1=C(C=CC(=C1)Br)OCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-Methoxybenzylchloride (0.6 mL, 4.4 mmol) was added to a mixture of 2,4-dibromo-phenol (1 g, 4 mmol) and potassium carbonate (0.61 g, 4.4 mmol) in DMF (20 mL) at room temperature. The resulting mixture was stirred at room temperature for 1 hr. After adding cesium carbonate (1.3 g, 4 mmol), the resulting mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | O.CN(C)C=O | null | 1 | COc1ccc(CCl)cc1.Oc1ccc(Br)cc1Br>O.CN(C)C=O>COc1ccc(COc2ccc(Br)cc2Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98563ff731384abeb2265dd327d01442 | COc1ccc(COc2ccc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)cc2C(=O)c2cccnc2)cc1>>O=C(c1cccnc1)c1cc(-c2cccc3[nH]ccc23)ccc1O | COC1=CC=C(COC2=C(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.C(=O)(C(F)(F)F)O.C(=O)(O)[O-].[Na+]>>OC1=C(C=C(C=C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC=CC1 | COc1ccc(C[O:24][c:23]2[c:9]([C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][n:7][cH:8]3)[cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]4[n:17]([Si](C(C)C)(C(C)C)C(C)C)[cH:18][cH:19][c:20]34)[cH:21][cH:22]2)cc1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]3[nH:17][cH:1... | COc1ccc(COc2ccc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)cc2C(=O)c2cccnc2)cc1 | O=C(c1cccnc1)c1cc(-c2cccc3[nH]ccc23)ccc1O | null | null | ClCCl.CSC | Reduction | OtherReaction | 63dde71090524dfe816aacbeb73220ede8c80fc03e995eb7b05c27dc4b663a4a | e0b1422bef25db45aecd1b91d52276549faecdaa4ba19e30ce4bb80cad333481 | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)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-O-c1:c:c:c(-C-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]=[O;D1;H0:12]):c:c:1>>[O;D1;H0:12]=[C:11]-[c:10]:[c:8](-[OH;D1;+0:7]):[c:9].[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 14.1 | [{"value": 14.0, "product": "OC1=C(C=C(C=C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.1, "product": "OC1=C(C=C(C=C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of [2-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone (42 mg, 0.07 mmol) in dichloromethane (0.5 mL) and dimethylsulfide (0.5 mL) at 0° C. was added TFA (1 mL) dropwise. After stirring at 0° C. for 30 mins, the starting material was gone. Saturated aqueous NaHC... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group | Aromatic alcohol | c1ccccc1.c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | ClCCl.CSC | 0 | 0.5 | COc1ccc(COc2ccc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)cc2C(=O)c2cccnc2)cc1>ClCCl.CSC>O=C(c1cccnc1)c1cc(-c2cccc3[nH]ccc23)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce2eec77f655423d968bc41519cfb9aa | O=C(c1cccnc1)c1cc(Br)cc(Br)c1>>O=C(c1cccnc1)c1cc(O)cc(Br)c1 | OOS(=O)[O-].[K+].BrC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.C(C)(=O)[O-].[K+]>>BrC=1C=C(C=C(C1)O)C(=O)C=1C=NC=CC1 | Br[c:11]1[cH:10][c:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][n:7][cH:8]2)[cH:16][c:14]([Br:15])[cH:13]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][c:11]([OH:12])[cH:13][c:14]([Br:15])[cH:16]1 | O=C(c1cccnc1)c1cc(Br)cc(Br)c1 | O=C(c1cccnc1)c1cc(O)cc(Br)c1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | CS(=O)C.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 7a3c53af18de91c78bb62d37ef80030b1c8a86f2645b966400b7ecee02318777 | 0a2c9c06cdf2e38a7b19edfe753c378fe9b4cd388941f2ee347592ac3cf825ba | O=C(c1ccccc1)c1cccnc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7]>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;D1;H1:8]):[c:6]:[c:7] | 57.4 | [{"value": 57.0, "product": "BrC=1C=C(C=C(C1)O)C(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "BrC=1C=C(C=C(C1)O)C(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 10 | MINUTE | A 50 mL tube was charged with (3,5-dibromo-phenyl)-pyridin-3-yl-methanone (2.55 g, 7.5 mmol), bis(pinacolato)diboron (1.26 g, 5.0 mmol), potassium acetate (1.47 g, 15.0 mmol) and Pd(dppf)Cl2.CH2Cl2 (200 mg). DMSO (15 mL) was added, and the solution was degassed with nitrogen, then the tube was sealed. After heating the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CS(=O)C.C(Cl)Cl | 80 | 0.166667 | O=C(c1cccnc1)c1cc(Br)cc(Br)c1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CS(=O)C.C(Cl)Cl>O=C(c1cccnc1)c1cc(O)cc(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c09b2d0ce09a4446b2e1f8618d3f89ac | N#Cc1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1.[OH-]>>NC(=O)c1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 | OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C=CC(=NC1)C#N.[OH-].[Na+]>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C=CC(=NC1)C(=O)N | [N:1]#[C:2][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([OH:12])[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]4[nH:20][cH:21][cH:22][c:23]34)[cH:24]2)[cH:25][n:26]1.[OH-:3]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([OH:12])[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]4[nH:20][cH... | N#Cc1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1.[OH-] | NC(=O)c1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 | null | null | O.OO.CO | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1cncc(Nc2cccc(-c3cccc4[nH]ccc34)c2)c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6].[OH-;D0:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:7])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 66 | [{"value": 66.0, "product": "OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C=CC(=NC1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carbonitrile (83 mg, 0.25 mmol) in MeOH (1 mL) was added 50% NaOH solution in H2O (200 μL) and 30% H2O2 (500 μL), and the mixture was stirred for 16 h at room temperature. The solution was concentrated to half the volume with a gentle stream of nit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | O.OO.CO | null | 16 | N#Cc1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1.[OH-]>O.OO.CO>NC(=O)c1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd02b07b92ea4fdab52c52bb2c8b01b1 | CC(C)[Si](Oc1cc(Br)cc(Br)c1)(C(C)C)C(C)C.N#Cc1ccc(N)cn1>>CC(C)[Si](Oc1cc(Br)cc(Nc2ccc(C#N)cc2)c1)(C(C)C)C(C)C | BrC=1C=C(C=C(C1)Br)O[Si](C(C)C)(C(C)C)C(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].NC=1C=CC(=NC1)C#N>>BrC=1C=C(C=C(C1)O[Si](C(C)C)(C(C)C)C(C)C)NC1=CC=C(C#N)C=C1 | Br[c:11]1[cH:10][c:8]([Br:9])[cH:7][c:6]([O:5][Si:4]([CH:2]([CH3:1])[CH3:3])([CH:22]([CH3:23])[CH3:24])[CH:25]([CH3:26])[CH3:27])[cH:21]1.n1[c:16]([C:17]#[N:18])[cH:19][cH:14][c:13]([NH2:12])[cH:20]1>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([C:17]#[N:1... | CC(C)[Si](Oc1cc(Br)cc(Br)c1)(C(C)C)C(C)C.N#Cc1ccc(N)cn1 | CC(C)[Si](Oc1cc(Br)cc(Nc2ccc(C#N)cc2)c1)(C(C)C)C(C)C | null | 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.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 | Heteroatom Alkylation and Arylation | OtherReaction | d3575605ef704e39f5c31dba6bb3eb892e53f07e413b2832327ec6b7a1589bfa | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11](-[NH2;D1;+0:12]):[cH;D2;+0:13]:n:1>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:8]1:[c:14]:[cH;D2;+0:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[cH;D2;+0:13]:[cH;D2;+0:9]:1 | 46.4 | [{"value": 46.4, "product": "BrC=1C=C(C=C(C1)O[Si](C(C)C)(C(C)C)C(C)C)NC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To 1.0 g (2.45 mmol) of 3,5-dibromotriisopropylsiloxybenzene in 20.0 mL of anhydrous 1,4-dioxane was added 1.12 g (3.43 mmol) of Cs2CO3, 0.32 g (2.7 mmol) of 5-amino-pyridine-2-carbonitrile and 43 mg (0.074 mmol) Xantphos. The reaction mixture was deoxygenated by bubbling argon for 30 mins and then treated with 57 mg (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | 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.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 | 100 | null | CC(C)[Si](Oc1cc(Br)cc(Br)c1)(C(C)C)C(C)C.N#Cc1ccc(N)cn1>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.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.O1CCOC... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e668e222400e4a6f880d1188d108b5b3 | CC(C)[Si](Oc1cc(Nc2ccc(C#N)nc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1)(C(C)C)C(C)C>>N#Cc1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 | BrC=1C=C(C=C(C1)O[Si](C(C)C)(C(C)C)C(C)C)NC1=CC=C(C#N)C=C1.C(C)(C)[Si](N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)O[Si](C(C)C)(C(C)C)C(C)C)NC=1C=CC(=NC1)C#N)(C(C)C)C(C)C>>OC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC=1C=CC(=NC1)C#N | CC(C)[Si](C(C)C)(C(C)C)[O:11][c:10]1[cH:9][c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[n:25][cH:24]2)[cH:23][c:13](-[c:14]2[cH:15][cH:16][cH:17][c:18]3[n:19]([Si](C(C)C)(C(C)C)C(C)C)[cH:20][cH:21][c:22]23)[cH:12]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][c:10]([OH:11])[cH:12][c:13](-[c:14]3[cH:15][cH:... | CC(C)[Si](Oc1cc(Nc2ccc(C#N)nc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1)(C(C)C)C(C)C | N#Cc1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 | null | null | null | Deprotection | OtherReaction | 2d5a0c60ff7f2e50457468ec0bb66db561b7f437299f695504ac5007f160b414 | 7a17b5a6213d7d750ed2c2a0e52dc8af429232c6fdbf2beedd471ef9f5f7f3f2 | 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-C(-C)-[Si](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])(-C(-C)-C)-C(-C)-C>>[OH;D1;+0:7]-[c:8](:[c:9]):[c:10].[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | null | [] | null | null | null | null | 4-(3-Bromo-5-triisopropylsilanyloxy-phenylamino)-benzonitrile was converted to 5-[3-(1-triisopropylsilanyl-1H-indol-4-yl)-5-triisopropylsilanyloxy-phenylamino]-pyridine-2-carbonitrile, and the triisopropylsilyl groups were removed with tetra n-butylammonium fluoride to give 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-p... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group.Silyl protective group | Aromatic alcohol | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CC(C)[Si](Oc1cc(Nc2ccc(C#N)nc2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1)(C(C)C)C(C)C>>N#Cc1ccc(Nc2cc(O)cc(-c3cccc4[nH]ccc34)c2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1895ad04c203471ca6ad0e5b449f9b51 | CNC.Nc1cc(Br)cc(C(=O)c2cccnc2)c1.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>>CN(C)C(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | NC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1.ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-].C(C)(C)N(CC)C(C)C.CNC>>BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)NC(N(C)C)=O | [CH3:1][NH:2][CH3:3].[NH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][n:19][cH:20]2)[cH:21]1.O=[N+]([O-])c1ccc(O[C:4](Cl)=[O:5])cc1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][n:19][cH:20]2)[cH:21]... | CNC.Nc1cc(Br)cc(C(=O)c2cccnc2)c1.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | CN(C)C(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 | null | null | N1=CC=CC=C1.C(Cl)Cl.C1CCOC1 | Acylation | OtherReaction | ff99b2060d6ce3e40d165249bc9093aa43725edec767fbde8ced0df64c62383b | 98aebc6d58d100f429173d34545e4a01ad4d63f23c63a0b359bb1da5bc08270a | O=C(c1ccccc1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c(-[N+](=O)-[O-]):c:c:1.[C;D1;H3:3]-[NH;D2;+0:4]-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | To 0.2 g (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.72 mmol) in 5 mL of methylene chloride was added 0.16 g of 4-nitrophenyl chloroformate (0.79 mmol) and 0.12 mL of pyridine. An additional 10 mL of methylene chloride was added, and the reaction was stirred for 3 hours at room temperature at which time 0.15 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Nitro group.Primary amine.Secondary amine | Urea | c1ccccc1 | null | c1ccccc1.c1ccncc1 | HCl | N1=CC=CC=C1.C(Cl)Cl.C1CCOC1 | null | 8 | CNC.Nc1cc(Br)cc(C(=O)c2cccnc2)c1.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>N1=CC=CC=C1.C(Cl)Cl.C1CCOC1>CN(C)C(=O)Nc1cc(Br)cc(C(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f1efc668ff44e5e949c0e45a7f3e243 | Brc1cc(Br)cc(Br)c1.CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3[nH]ccc23)c1.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1 | ClC1=NC=CC(=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC(C)=O.BrC1=CC(=CC(=C1)Br)Br.ClC=1C=C(C#N)C=CN1.ClC1=NC=CC(=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC(C)=O>>ClC1=NC=CC(=C1)C(=O)C1=CC(=CC(=C1)Br)Br.ClC1=NC=CC(=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)NC(C)=O | Brc1c[c:33]([Br:34])[cH:35][c:36]([Br:37])c1.CC(C)[Si](C(C)C)(C(C)C)[n:24]1[c:23]2[cH:22][cH:21][cH:20][c:19](-[c:18]3[cH:17][c:7]([C:8](=[O:9])[c:10]4[cH:11][cH:12][n:13][c:14]([Cl:15])[cH:16]4)[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:28]3)[c:27]2[cH:26][cH:25]1.CC(=O)Nc1cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)[cH:... | Brc1cc(Br)cc(Br)c1.CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3[nH]ccc23)c1.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1 | null | null | null | Miscellaneous | OtherReaction | 7dcce32b7758de4db959ee48a87fc57a2e140a25c50a9cbe3e2daa79e53ae682 | d5bb1724f1fa73b6cf9465215a8e039786a7b654678c29ab34e5f82311a720f9 | O=C(c1ccccc1)c1ccncc1.O=C(c1ccncc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-c1:c:[c;H0;D3;+0:1](-[Br;D1;H0:2]):[c:3]:[c;H0;D3;+0:4](-[Br;D1;H0:5]):c:1.C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[c:10]:1:[c:11].C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-n1:c:c:c2:c(-c3:[cH;D2;+0:12]:[c:13](-[C:14](=[O;D1;H0:15])-[c:16]):[cH;D2;+0:17]:c(-N-C(-C)=O):c:3):c:c:c:c:2:1>>[Br;D1;H0:2]... | null | [] | null | null | null | null | (2-Chloro-pyridin-4-yl)-(3,5-dibromo-phenyl)-methanone was prepared from 1,3,5-tribromobenzene and 2-chloro-isonicotinonitrile as described in Example 25. This was converted to N-[3-(2-chloro-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide in the same manner as described for Example 82. N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Secondary amide.Silyl protective group.Silyl protective group | Aromatic halide.Aromatic halide | c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1.c1ccccc1.c1ccncc1 | HBr | null | null | null | Brc1cc(Br)cc(Br)c1.CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3[nH]ccc23)c1.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55753a3062bd498994465846621d4331 | CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.C[O-]>>COc1cc(C(=O)c2cc(NC(C)=O)cc(-c3cccc4[nH]ccc34)c2)ccn1 | ClC1=NC=CC(=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC(C)=O.C[O-].[Na+]>>N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)C(=O)C1=CC(=NC=C1)OC)NC(C)=O | CC(C)[Si](C(C)C)(C(C)C)[n:22]1[c:21]2[cH:20][cH:19][cH:18][c:17](-[c:16]3[cH:15][c:10]([NH:11][C:12]([CH3:13])=[O:14])[cH:9][c:8]([C:6]([c:5]4[cH:4][c:3](Cl)[n:29][cH:28][cH:27]4)=[O:7])[cH:26]3)[c:25]2[cH:24][cH:23]1.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][c:10]([NH:11][C:12]([CH3:13])=[... | CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.C[O-] | COc1cc(C(=O)c2cc(NC(C)=O)cc(-c3cccc4[nH]ccc34)c2)ccn1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c68473ba204b1ecd75e203f888ea783e84da868ebd11f0a7ea0e22c0fdf47aa6 | 075aa9549749ddd580161f7f04e0f5d5703a5018218dfca1bda3e5fc6a908eba | O=C(c1ccncc1)c1cccc(-c2cccc3[nH]ccc23)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].Cl-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]-[C:12]=[O;D1;H0:13].[C;D1;H3:14]-[O-;H0;D1:15]>>[C;D1;H3:14]-[O;H0;D2;+0:15]-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]-[C:12]=[O;D1;H0:13].[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 11.8 | [{"value": 11.8, "product": "N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)C(=O)C1=CC(=NC=C1)OC)NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To N-[3-(2-Chloro-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide (Example 83, 0.120 g, 0.22 mmol) in 25 mL of anhydrous methanol was added 0.036 g (0.66 mmol) NaOMe. The reaction mixture was refluxed overnight. The methanol was removed under vacuum and water added to the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Silyl protective group | Ether | c1cccc2[nH]ccc12.c1ccncc1 | c1ccncc1.c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | CO | null | null | CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.C[O-]>CO>COc1cc(C(=O)c2cc(NC(C)=O)cc(-c3cccc4[nH]ccc34)c2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a7b2a0b8e31455a800d0c63702ad7c8 | CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.C[O-]>>COc1cc(C(=O)c2cc(N)cc(-c3cccc4[nH]ccc34)c2)ccn1 | ClC1=NC=CC(=C1)C(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC(C)=O.C[O-].[Na+]>>NC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C1=CC(=NC=C1)OC | CC(=O)[NH:11][c:10]1[cH:9][c:8]([C:6]([c:5]2[cH:4][c:3](Cl)[n:26][cH:25][cH:24]2)=[O:7])[cH:23][c:13](-[c:14]2[cH:15][cH:16][cH:17][c:18]3[n:19]([Si](C(C)C)(C(C)C)C(C)C)[cH:20][cH:21][c:22]23)[cH:12]1.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][c:10]([NH2:11])[cH:12][c:13](-[c:14]3[cH:15][cH:... | CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.C[O-] | COc1cc(C(=O)c2cc(N)cc(-c3cccc4[nH]ccc34)c2)ccn1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 6ed9fa24e29da8898c0d5b976d6416dc1c802e1c09d4e873f889948f5ff46f9c | 4471b743a91526e4ad3ee4906570a864db0d05613ac6d8755a194bb388a5093a | O=C(c1ccncc1)c1cccc(-c2cccc3[nH]ccc23)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(=O)-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10].Cl-[c;H0;D3;+0:11](:[#7;a:12]:[c:13]):[c:14]:[c:15]-[C:16]=[O;D1;H0:17].[C;D1;H3:18]-[O-;H0;D1:19]>>[C;D1;H3:18]-[O;H0;D2;+0:19]-[c;H0;D3;+0:11](:[#7;a:12]:[c:13]):[c:14]:[c:15]-[C:16]=[O;D1;H0:17]... | 12.9 | [{"value": 12.9, "product": "NC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)C(=O)C1=CC(=NC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To N-[3-(2-Chloro-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide (Example 83, 0.150 g, 0.27 mmol) in 25 mL of anhydrous methanol was added 0.022 g (0.41 mmol) NaOMe. The reaction mixture was refluxed overnight. The methanol was removed under vacuum and water was added to the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide.Silyl protective group | Ether.Primary amine | c1ccncc1.c1cccc2[nH]ccc12 | c1ccncc1.c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | CO | null | null | CC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1.C[O-]>CO>COc1cc(C(=O)c2cc(N)cc(-c3cccc4[nH]ccc34)c2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e72776a19224d0aaa321979d502a209 | CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2ccnc(Cl)c2)c1.C[O-]>>COc1cc(C(=O)c2cc(Br)cc(NS(C)(=O)=O)c2)ccn1 | BrC=1C=C(C=C(C1)C(=O)C1=CC(=NC=C1)Cl)NS(=O)(=O)C.C[O-].[Na+]>>BrC=1C=C(C=C(C1)C(=O)C1=CC(=NC=C1)OC)NS(=O)(=O)C | Cl[c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][c:10]([Br:11])[cH:12][c:13]([NH:14][S:15]([CH3:16])(=[O:17])=[O:18])[cH:19]2)[cH:20][cH:21][n:22]1.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][c:10]([Br:11])[cH:12][c:13]([NH:14][S:15]([CH3:16])(=[O:17])=[O:18])[cH:19]2)[cH:20][cH:21][n:22]1 | CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2ccnc(Cl)c2)c1.C[O-] | COc1cc(C(=O)c2cc(Br)cc(NS(C)(=O)=O)c2)ccn1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 600484490705932a09b3fac6538a42c6f3fc156ab44a4ea0bbd020dd3eafd6ff | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=C(c1ccccc1)c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6]=[O;D1;H0:7].[C;D1;H3:8]-[O-;H0;D1:9]>>[C;D1;H3:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6]=[O;D1;H0:7] | 43.3 | [{"value": 43.3, "product": "BrC=1C=C(C=C(C1)C(=O)C1=CC(=NC=C1)OC)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a mixture of 0.080 g (0.21 mmol) of N-[3-bromo-5-(2-chloro-pyridine-4-carbonyl)-phenyl]-methanesulfonamide in 10.0 mL of anhydrous methanol in a pressure tube was added 0.007 g (0.21 mmol) of sodium methoxide. The tube was sealed and the reaction was heated at 80° C. for 18 hours. The methanol was removed under vacu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | Other | CO | 80 | null | CS(=O)(=O)Nc1cc(Br)cc(C(=O)c2ccnc(Cl)c2)c1.C[O-]>CO>COc1cc(C(=O)c2cc(Br)cc(NS(C)(=O)=O)c2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8fc32e507c447a2a572342e7c9afc4b | CNOC.Cc1cc(C(=O)O)cc(Cl)n1>>CON(C)C(=O)c1cc(C)nc(Cl)c1 | C(C)(C)N(CC)C(C)C.CONC.ClC=1C=C(C(=O)O)C=C(N1)C.O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>ClC=1C=C(C(=O)N(C)OC)C=C(N1)C | [CH3:1][O:2][NH:3][CH3:4].O[C:5](=[O:6])[c:7]1[cH:8][c:9]([CH3:10])[n:11][c:12]([Cl:13])[cH:14]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([CH3:10])[n:11][c:12]([Cl:13])[cH:14]1 | CNOC.Cc1cc(C(=O)O)cc(Cl)n1 | CON(C)C(=O)c1cc(C)nc(Cl)c1 | null | null | O.CN(C)C=O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[#8:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C;D1;H3:9]-[#8:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 57.6 | [{"value": 57.6, "product": "ClC=1C=C(C(=O)N(C)OC)C=C(N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | To 0.500 g (2.91 mmol) 2-chloro-6-methyl-isonicotinic acid in 5.0 mL of anhydrous methylene chloride and 0.5 mL of anhydrous DMF was added 0.47 g (3.5 mmol) 1-hydroxybenzotriazole hydrate. The reaction mixture was stirred for 20 minutes at 0° C. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.67 g, 3.5 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccncc1 | HO- | O.CN(C)C=O.C(Cl)Cl | 0 | 0.333333 | CNOC.Cc1cc(C(=O)O)cc(Cl)n1>O.CN(C)C=O.C(Cl)Cl>CON(C)C(=O)c1cc(C)nc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccb9c1d832214addb7fa98780978663c | Brc1cc(Br)cc(Br)c1.CON(C)C(=O)c1cc(C)nc(Cl)c1>>Cc1cc(C(=O)c2cc(Br)cc(Br)c2)cc(Cl)n1 | C([O-])(O)=O.[Na+].ClC=1C=C(C(=O)N(C)OC)C=C(N1)C.BrC1=CC(=CC(=C1)Br)Br.[Li]CCCC>>ClC1=NC(=CC(=C1)C(=O)C1=CC(=CC(=C1)Br)Br)C | Br[c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([Br:13])[cH:14]1.CON(C)[C:5]([c:4]1[cH:3][c:2]([CH3:1])[n:18][c:16]([Cl:17])[cH:15]1)=[O:6]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][c:12]([Br:13])[cH:14]2)[cH:15][c:16]([Cl:17])[n:18]1 | Brc1cc(Br)cc(Br)c1.CON(C)C(=O)c1cc(C)nc(Cl)c1 | Cc1cc(C(=O)c2cc(Br)cc(Br)c2)cc(Cl)n1 | null | null | CCOCC.C(C)(=O)OCC.C1CCOC1 | C-C Coupling | OtherReaction | 99face78a8bbaa38ff4dd2141c4a0df3e690005988b6fb5a9a2afc6a90da7e24 | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | O=C(c1ccccc1)c1ccncc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-O-N(-C)-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 77 | [{"value": 77.0, "product": "ClC1=NC(=CC(=C1)C(=O)C1=CC(=CC(=C1)Br)Br)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "ClC1=NC(=CC(=C1)C(=O)C1=CC(=CC(=C1)Br)Br)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | To 0.45 grams (1.4 mmol) of 1,3,5-tribromobenzene in 25.0 mL of anhydrous ether at −78° C. was added 0.57 mL of 2.5 M n-BuLi (1.4 mmol) at a rate that maintained the internal temperature of the reaction at less than −70° C. After the addition was complete, the reaction was stirred 1 hour at −78° C., then 0.220 grams (1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | CCOCC.C(C)(=O)OCC.C1CCOC1 | -78 | 1 | Brc1cc(Br)cc(Br)c1.CON(C)C(=O)c1cc(C)nc(Cl)c1>CCOCC.C(C)(=O)OCC.C1CCOC1>Cc1cc(C(=O)c2cc(Br)cc(Br)c2)cc(Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c068807f0c4a46f494b4226691e4f68e | CB(O)O.COC(=O)Nc1cc(C(=O)c2cc(C)nc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>>COC(=O)Nc1cc(C(=O)c2cc(C)nc(C)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | COC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C1=CC(=NC(=C1)C)Cl)=O.C([O-])([O-])=O.[K+].[K+].CB(O)O>>COC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C1=CC(=NC(=C1)C)C)=O | OB(O)[CH3:17].Cl[c:16]1[n:15][c:13]([CH3:14])[cH:12][c:11]([C:9]([c:8]2[cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:40][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]4[c:26]3[cH:27][cH:28][n:29]4[Si:30]([CH:31]([CH3:32])[CH3:33])([CH:34]([CH3:35])[CH3:36])[CH:37]([CH3:38])[CH3:39])[cH:19]2)=[O:10])[cH:18]1>>[CH3:1][O:2][... | CB(O)O.COC(=O)Nc1cc(C(=O)c2cc(C)nc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | COC(=O)Nc1cc(C(=O)c2cc(C)nc(C)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1 | 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.O | C-C Coupling | Suzuki coupling with boronic acids | e6427a06cf763f629ade010ec8edb6d572dcafeb9186c64e3948e154bc0e8e0d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccncc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6]=[O;D1;H0:7].O-B(-O)-[CH3;D1;+0:8]>>[CH3;D1;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6]=[O;D1;H0:7] | 62 | [{"value": 62.0, "product": "COC(NC1=CC(=CC(=C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)C(=O)C1=CC(=NC(=C1)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | To 0.100 g (0.174 mmol) [3-(2-chloro-6-methyl-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester in 2.0 mL of anhydrous dioxane in a pressure tube was added 0.034 g (0.24 mmol) potassium carbonate and 0.015 g (0.24 mmol) methylboronic acid. The reaction mixture was degassed ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cccc2[nH]ccc12 | HCl.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.O1CCOCC1.O | 110 | null | CB(O)O.COC(=O)Nc1cc(C(=O)c2cc(C)nc(Cl)c2)cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)c1>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.O>COC(=O)Nc1cc(C(=O)c2cc(C)nc(C)c2)cc(-c2cccc3c2ccn3[Si... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36127330c5584e7fa7702fe68790e3b4 | COC(=O)Nc1cc(Br)cc(C(=O)c2ccnc(Cl)c2)c1.COC(N)=O.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1>>COC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3[nH]ccc23)c1 | ClC1=NC=CC(=C1)C(=O)C1=CC(=CC(=C1)Br)Br.COC(NC1=CC(=CC(=C1)C(=O)C1=CC(=NC=C1)Cl)Br)=O.COC(N)=O>>COC(NC1=CC(=CC(=C1)C1=C2C=CNC2=CC=C1)C(=O)C1=CC(=NC=C1)Cl)=O | Br[c:19]1[cH:18][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][n:14][c:15]([Cl:16])[cH:17]2)[cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:29]1.CO[C:26](=O)[NH2:25].O=[C:20]([c:21]1ccn[c:24](Cl)c1)[c:28]1cc(Br)[cH:23][c:22](Br)[cH:27]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][n:... | COC(=O)Nc1cc(Br)cc(C(=O)c2ccnc(Cl)c2)c1.COC(N)=O.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1 | COC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3[nH]ccc23)c1 | null | [Pd] | null | C-C Coupling | OtherReaction | 48938f901b1c0685435765bd166a333ac1d5c29a0c53a6ce830bc8d1754a8114 | ab52103621fbd81542a3ff2f55c181fa9d4e6c50d499fad054423188198d9094 | O=C(c1ccncc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].Br-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:c(-Br):c:[c;H0;D3;+0:10](-[C;H0;D3;+0:11](=O)-[c;H0;D3;+0:12]2:c:c:n:[c;H0;D3;+0:13](-Cl):c:2):[cH;D2;+0:14]:1.C-O-[C;H0;D3;+0:15](=O)-[NH2;D1;+0:16]>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11]1:[cH;D2;+0:12... | null | [] | null | null | null | null | (2-Chloro-pyridin-4-yl)-(3,5-dibromo-phenyl)-methanone was converted to [3-bromo-5-(2-chloro-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester under the palladium catalyzed conditions described for Example 86, using carbamic acid methyl ester in place of methanesulfonamide. The Suzuki reaction and removal of the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Carbamic ester.Ketone.Ether | null | c1ccccc1.c1ccncc1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1ccc2[nH]ccc2c1 | HCl.Br- | [Pd] | null | null | COC(=O)Nc1cc(Br)cc(C(=O)c2ccnc(Cl)c2)c1.COC(N)=O.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1>[Pd]>COC(=O)Nc1cc(C(=O)c2ccnc(Cl)c2)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90586a893ad24e0db7054077ceb13cb3 | C1COCCN1.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1>>O=C(c1cc(Br)cc(Br)c1)c1ccnc(N2CCOCC2)c1 | ClC1=NC=CC(=C1)C(=O)C1=CC(=CC(=C1)Br)Br.N1CCOCC1>>BrC=1C=C(C=C(C1)Br)C(=O)C1=CC(=NC=C1)N1CCOCC1 | [NH:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1.Cl[c:15]1[n:14][cH:13][cH:12][c:11]([C:2](=[O:1])[c:3]2[cH:4][c:5]([Br:6])[cH:7][c:8]([Br:9])[cH:10]2)[cH:22]1>>[O:1]=[C:2]([c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([Br:9])[cH:10]1)[c:11]1[cH:12][cH:13][n:14][c:15]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[cH:22]1 | C1COCCN1.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1 | O=C(c1cc(Br)cc(Br)c1)c1ccnc(N2CCOCC2)c1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1ccccc1)c1ccnc(N2CCOCC2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]-[C:6]=[O;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[O;D1;H0:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1):[#7;a:2]:[c:3] | 52.3 | [{"value": 52.3, "product": "BrC=1C=C(C=C(C1)Br)C(=O)C1=CC(=NC=C1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To (2-chloro-pyridin-4-yl)-(3,5-dibromo-phenyl)-methanone (0.200 g, 0.53 mmol) in 1.0 mL of 1,4-dioxane in a microwave tube was added 0.070 g (0.80 mmol) morpholine. The reaction was subjected to microwave irradiation at 120° C. for 60 minutes. The reaction mixture was cooled and concentrated. The crude product was chr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccccc1.c1ccncc1.C1COCC[NH]1 | HCl | O1CCOCC1 | null | null | C1COCCN1.O=C(c1cc(Br)cc(Br)c1)c1ccnc(Cl)c1>O1CCOCC1>O=C(c1cc(Br)cc(Br)c1)c1ccnc(N2CCOCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4902999dbd14def8e1e030623f1b029 | O=C(c1cccnc1)c1cc(Br)cc(Br)c1.O=C1CCCN1>>O=C(c1cccnc1)c1cc(Br)cc(N2CCCC2=O)c1 | BrC=1C=C(C=C(C1)Br)C(=O)C=1C=NC=CC1.C([O-])([O-])=O.[Cs+].[Cs+].CNCCNC.N1C(CCC1)=O>>BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)N1C(CCC1)=O | Br[c:14]1[cH:13][c:11]([Br:12])[cH:10][c:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][n:7][cH:8]2)[cH:21]1.[NH:15]1[CH2:16][CH2:17][CH2:18][C:19]1=[O:20]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][c:11]([Br:12])[cH:13][c:14]([N:15]2[CH2:16][CH2:17][CH2:18][C:19]2=[O:20])[cH:21]1 | O=C(c1cccnc1)c1cc(Br)cc(Br)c1.O=C1CCCN1 | O=C(c1cccnc1)c1cc(Br)cc(N2CCCC2=O)c1 | null | [Cu]I | O1CCOCC1 | Heteroatom Alkylation and Arylation | Goldberg coupling | f6dabce0e556a3bc4252c63b536c694b4525d2ce7193f8af0c0c6646e77b4515 | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C(c1cccnc1)c1cccc(N2CCCC2=O)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[O;D1;H0:7].[O;D1;H0:8]=[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[O;D1;H0:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[C:10]-[C:9]-1=[O;D1;H0:8]):[c:2]:[c:3] | 7.2 | [{"value": 7.2, "product": "BrC=1C=C(C=C(C1)C(=O)C=1C=NC=CC1)N1C(CCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a nitrogen-flushed tube were added 0.20 grams (0.72 mmol) (3,5-dibromo-phenyl)-pyridin-3-yl-methanone, 0.137 g (0.72 mmol) copper (I) iodide, 0.235 (0.72 mmol) cesium carbonate, 0.063 g (0.72 mmol) N,N′-dimethyl-ethane-1,2-diamine, 0.061 g (0.72 mmol) pyrrolidin-2-one and 5 mL dioxane. The tube was sealed and heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Tertiary amide | c1ccccc1.C1CCNC1 | c1ccccc1.C1CC[NH]C1 | c1ccncc1.c1ccccc1.C1CC[NH]C1 | HBr | [Cu]I.O1CCOCC1 | 80 | null | O=C(c1cccnc1)c1cc(Br)cc(Br)c1.O=C1CCCN1>[Cu]I.O1CCOCC1>O=C(c1cccnc1)c1cc(Br)cc(N2CCCC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04cd896dfc38491abdc158aa0159c304 | N#Cc1cc2c(O)cccc2[nH]1.O=S(=O)([O-])C(F)(F)F>>N#Cc1cc2c(OS(=O)(=O)C(F)(F)F)cccc2[nH]1 | OC1=C2C=C(NC2=CC=C1)C#N.[O-]S(=O)(=O)C(F)(F)F>>C(#N)C=1NC2=CC=CC(=C2C1)OS(=O)(=O)C(F)(F)F | [N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([OH:7])[cH:15][cH:16][cH:17][c:18]2[nH:19]1.[O-][S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14]>>[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([O:7][S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17][c:18]2[nH:19]1 | N#Cc1cc2c(O)cccc2[nH]1.O=S(=O)([O-])C(F)(F)F | N#Cc1cc2c(OS(=O)(=O)C(F)(F)F)cccc2[nH]1 | null | null | null | Miscellaneous | OtherReaction | ba84d08741dc57cca837179da107c727f33f41827c881049a0cab23247fbb369 | fcecc986e6b6ef358a6dd65b54f52d1bac6e13854a99d0d8523194ad4b1de7ad | c1ccc2[nH]ccc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6].[F;D1;H0:7]-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[S;H0;D4;+0:11](-[O-])(=[O;D1;H0:12])=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-[S;H0;D4;+0:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[C:8](-[F;D1;H0:7])(-[F;D1;H0:9])-[F;D1;H0:10]):[c:6] | null | [] | null | null | null | null | 4-Hydroxy-1H-indole-2-carbonitrile was made as described by Estep, K. G., Synth. Comm. 25: 507-14 (1995). It was converted to the triflate by the procedure in Example 21.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfonic acid | Triflate | null | null | c1ccc2[nH]ccc2c1 | HO- | null | null | null | N#Cc1cc2c(O)cccc2[nH]1.O=S(=O)([O-])C(F)(F)F>>N#Cc1cc2c(OS(=O)(=O)C(F)(F)F)cccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-102fc239cdc54307991e1b80dd3df6e3 | COC(=O)Nc1cc(Br)cc(C(=O)c2ccnc(OC)c2)c1.O=S(=O)(Oc1cccc2occc12)C(F)(F)F>>COC(=O)Nc1cc(C(=O)c2ccnc(OC)c2)ccc1-c1cccc2occc12 | COC(NC1=CC(=CC(=C1)C(=O)C1=CC(=NC=C1)OC)Br)=O.O1C=CC2=C1C=CC=C2OS(=O)(=O)C(F)(F)F.CC1(OB(OC1(C)C)C1=CC=CC2=C1C=CO2)C.CC1(OB(OC1(C)C)C1=CC=CC2=C1C=CO2)C>>COC(NC1=C(C=CC(=C1)C(=O)C1=CC(=NC=C1)OC)C1=CC=CC=2OC=CC21)=O | Br[c:20]1[cH:19][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][n:14][c:15]([O:16][CH3:17])[cH:18]2)[cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:21]1.O=S(=O)(O[c:22]1[cH:23][cH:24][cH:25][c:26]2[o:27][cH:28][cH:29][c:30]12)C(F)(F)F>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][n:14]... | COC(=O)Nc1cc(Br)cc(C(=O)c2ccnc(OC)c2)c1.O=S(=O)(Oc1cccc2occc12)C(F)(F)F | COC(=O)Nc1cc(C(=O)c2ccnc(OC)c2)ccc1-c1cccc2occc12 | null | null | null | C-C Coupling | OtherReaction | bcbe213216ac7535648ed03236c23d6b931d4237ad27ef135300e77d2eb9d884 | 6fa0c5f5a567aef7a3c8790e894c3eacfb3f5a56b34ccd5ba5e56676973c2603 | O=C(c1ccncc1)c1ccc(-c2cccc3occc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6]:[c:7](-[#7:8]-[C:9]=[O;D1;H0:10]):[cH;D2;+0:11]:1.F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c:15]:[c:16]2:[#8;a:17]:[c:18]:[c:19]:[c:20]:2:1>>[O;D1;H0:5]=[C:4]-[c:3]1:[c:2]:[cH;D2;+0:1]:[c;H0;D3;+0:11](-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[c:15]:[c:16]3:... | null | [] | null | null | null | null | Trifluoro-methanesulfonic acid benzofuran-4-yl ester was converted to 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzofuran using conditions described in Wang, Y.-C. and Georghiou, P. E., Org. Lett. 4: 2675-78 (2002). The Suzuki coupling of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzofuran to [3-bromo-5... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Aromatic halide | null | c1ccccc1.c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | c1ccccc1.c1ccncc1.c1ccc2occc2c1 | TfOH.Br- | null | null | null | COC(=O)Nc1cc(Br)cc(C(=O)c2ccnc(OC)c2)c1.O=S(=O)(Oc1cccc2occc12)C(F)(F)F>>COC(=O)Nc1cc(C(=O)c2ccnc(OC)c2)ccc1-c1cccc2occc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9bc5d12d03d845a8b0bc4a3b31c4ecde | COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.OB(O)c1cccnc1>>COc1ccc(COc2cc(-c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | 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.C([O-])([O-])=O.[Na+].[Na+].N1C=CC2=CC=CC=C12.N1=CC(=CC=C1)B(O)O>>COC1=CC=C(COC=2C=C(C=C(C2)C=2C=NC=CC2)C2=C3C=CN(C3=CC=C2)[Si](C(C)C)(C(C)C)C(C)C)C=C1 | 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:41][cH:40]2)[cH:39][c:19](-[c:20]2[cH:21][cH:22][cH:23][c:24]3[c:25]2[cH:26][cH:27][n:28]3[Si:29]([CH:30]([CH3:31])[CH3:32])([CH:33]([CH3:34])[CH3:35])[CH:36]([CH3:37])[CH3:38])[cH:18]1.OB(O)[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[CH3:1][O:... | COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.OB(O)c1cccnc1 | COc1ccc(COc2cc(-c3cccnc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.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.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(COc2cc(-c3cccnc3)cc(-c3cccc4[nH]ccc34)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1):[c:2]:[c:3] | 46 | [{"value": 46.0, "product": "COC1=CC=C(COC=2C=C(C=C(C2)C=2C=NC=CC2)C2=C3C=CN(C3=CC=C2)[Si](C(C)C)(C(C)C)C(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a 30 mL vial equipped with stir-bar was added 0.400 g (0.71 mmol) 4-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-1-triisopropylsilanyl-1H-indole followed by 0.096 g (0.78 mmol) 3-pyridinyl boronic acid, 3 mL toluene, 3 mL ethanol, 0.71 mL 2 M aqueous sodium carbonate and 0.011 g (0.035 mmol) tetra n-butylammonium bromid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccccc1.c1ccncc1.c1cccc2[nH]ccc12 | HBr.B | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.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.C1(=CC=CC=C1)C.C(C)O | 100 | null | COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.OB(O)c1cccnc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.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.C1(=CC=CC=C1)C.C(C)O>COc1ccc(... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47da3b62b0ca484182c331a20b832d04 | Brc1cc(Br)cc(Br)c1.Nc1cccnc1>>Brc1cc(Br)cc(Nc2cccnc2)c1 | NC=1C=NC=CC1.BrC1=CC(=CC(=C1)Br)Br>>BrC=1C=C(C=C(C1)Br)NC=1C=NC=CC1 | Br[c:7]1[cH:6][c:4]([Br:5])[cH:3][c:2]([Br:1])[cH:15]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1>>[Br: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 | Brc1cc(Br)cc(Br)c1.Nc1cccnc1 | Brc1cc(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-Aminopyridine was coupled with 1,3,5-tribromobenzene to give (3,5-dibromo-phenyl)-pyridin-3-yl-amine by the method described in Example 44. The reaction was complete in 1 hour. The dibromide was converted to N-[3-bromo-5-(pyridin-3-ylamino)-phenyl]-acetamide by the method of Example 82.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HBr | null | null | null | Brc1cc(Br)cc(Br)c1.Nc1cccnc1>>Brc1cc(Br)cc(Nc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8bd94637e9242c58bd661a4c37616a5 | Brc1cc(Br)cc(Br)c1.N#Cc1ccc(N)cn1>>N#Cc1ccc(Nc2cc(Br)cc(Br)c2)cn1 | NC=1C=CC(=NC1)C#N.BrC1=CC(=CC(=C1)Br)Br>>BrC=1C=C(C=C(C1)Br)NC=1C=CC(=NC1)C#N | Br[c:8]1[cH:9][c:10]([Br:11])[cH:12][c:13]([Br:14])[cH:15]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:16][n:17]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][c:13]([Br:14])[cH:15]2)[cH:16][n:17]1 | Brc1cc(Br)cc(Br)c1.N#Cc1ccc(N)cn1 | N#Cc1ccc(Nc2cc(Br)cc(Br)c2)cn1 | 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:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | 5-Amino-pyridine-2-carbonitrile was coupled with 1,3,5-tribromobenzene to give 5-(3,5-dibromo-phenylamino)-pyridine-2-carbonitrile by the method described in Example 44. 5-(3,5-Dibromo-phenylamino)-pyridine-2-carbonitrile was converted to [3-bromo-5-(6-cyano-pyridin-3-ylamino)-phenyl]-carbamic acid methyl ester using t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | null | null | null | Brc1cc(Br)cc(Br)c1.N#Cc1ccc(N)cn1>>N#Cc1ccc(Nc2cc(Br)cc(Br)c2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8868586ea3dd4717b90f394488669e67 | COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.N#Cc1ccc(N)cc1>>COc1ccc(COc2cc(Nc3ccc(C#N)cc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | 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.NC1=CC=C(C#N)C=C1>>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)NC2=CC=C(C#N)C=C2)C=C1 | 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: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.[NH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][c... | COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.N#Cc1ccc(N)cc1 | COc1ccc(COc2cc(Nc3ccc(C#N)cc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2cc(Nc3ccccc3)cc(-c3cccc4[nH]ccc34)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]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | null | null | null | null | 4-[3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-1-triisopropylsilanyl-1H-indole was coupled with 4-amino-benzonitrile to give 4-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenylamino]-benzonitrile using the conditions of Example 80. This compound was deprotected to give 4-[3-hydroxy-5-(1H-indol-4-yl)-p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1cccc2[nH]ccc12 | HBr | null | null | null | COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1.N#Cc1ccc(N)cc1>>COc1ccc(COc2cc(Nc3ccc(C#N)cc3)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4708cdf3136740148e74c87a84be9659 | Nc1ncccc1O.O=C(O)c1cc(Br)cc(Br)c1>>Brc1cc(Br)cc(-c2nc3ncccc3o2)c1 | BrC=1C=C(C(=O)O)C=C(C1)Br.NC1=NC=CC=C1O>>BrC=1C=C(C=C(C1)Br)C=1OC=2C(=NC=CC2)N1 | [NH2:9][c:10]1[n:11][cH:12][cH:13][cH:14][c:15]1[OH:16].O=[C:8](O)[c:7]1[cH:6][c:4]([Br:5])[cH:3][c:2]([Br:1])[cH:17]1>>[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7](-[c:8]2[n:9][c:10]3[n:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17]1 | Nc1ncccc1O.O=C(O)c1cc(Br)cc(Br)c1 | Brc1cc(Br)cc(-c2nc3ncccc3o2)c1 | null | null | null | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | a070d4bbe848c5c302d9a11e414aef5399f3e53373b6b4721e984bea2f224fef | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ncccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[c:11](-[OH;D1;+0:12]):[c:13]>>[c:10]:[#7;a:9]:[c:8]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[o;H0;D2;+0:12]:[c:11]:1:[c:13] | null | [] | null | null | null | null | 3,5-Dibromo-benzoic acid and 2-amino-pyridin-3-ol were condensed to give 2-(3,5-dibromo-phenyl)-oxazolo[4,5-b]pyridine using the conditions of Clark, R. L., et al., J. Med. Chem. 21: 1158-62 (1978). This compound was converted to N-(3-bromo-5-oxazolo[4,5-b]pyridin-2-yl-phenyl)-acetamide as described in Example 82. Conv... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccncc1 | c1cnc2ncoc2c1 | c1ccccc1.c1cnc2ncoc2c1 | HO- | null | null | null | Nc1ncccc1O.O=C(O)c1cc(Br)cc(Br)c1>>Brc1cc(Br)cc(-c2nc3ncccc3o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea78a04bfc5d496984b271659bc10868 | Nc1ccccc1O.O=C(O)c1cc(Br)cc(Br)c1>>Brc1cc(Br)cc(-c2nc3ccccc3o2)c1 | BrC=1C=C(C(=O)O)C=C(C1)Br.NC1=C(C=CC=C1)O>>BrC=1C=C(C=C(C1)Br)C=1OC2=C(N1)C=CC=C2 | [NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[OH:16].O=[C:8](O)[c:7]1[cH:6][c:4]([Br:5])[cH:3][c:2]([Br:1])[cH:17]1>>[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17]1 | Nc1ccccc1O.O=C(O)c1cc(Br)cc(Br)c1 | Brc1cc(Br)cc(-c2nc3ccccc3o2)c1 | null | null | null | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:9]:[c:8]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[o;H0;D2;+0:11]:[c:10]:1:[c:12] | null | [] | null | null | null | null | 3,5-Dibromo-benzoic acid and 2-aminophenol were condensed to give 2-(3,5-dibromo-phenyl)-benzoxazole, which was converted to N-[3-benzoxazol-2-yl-5-(1H-indol-4-yl)-phenyl]-acetamide as described in Example 106. 1H NMR (400 MHz, DMSO-d6): δ 11.35 (s, 1H), 10.36 (s, 1H), 8.57 (t, J=1.6 Hz, 1H), 8.13 (d, J=1.6 Hz, 2H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | null | null | null | Nc1ccccc1O.O=C(O)c1cc(Br)cc(Br)c1>>Brc1cc(Br)cc(-c2nc3ccccc3o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c921fa3934a246efafb7e0885251b9e0 | Brc1cc(Br)cc(-c2nc3ccccc3o2)c1.NC(=O)OCc1ccccc1>>O=C(Nc1cc(Br)cc(-c2nc3ccccc3o2)c1)OCc1ccccc1 | BrC=1C=C(C=C(C1)Br)C=1OC2=C(N1)C=CC=C2.C(C1=CC=CC=C1)OC(N)=O.C([O-])([O-])=O.[Cs+].[Cs+].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>>C(C1=CC=CC=C1)OC(NC1=CC(=CC(=C1)Br)C=1OC2=C(N1)C=CC=C2)=O | Br[c:4]1[cH:5][c:6]([Br:7])[cH:8][c:9](-[c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[o:18]2)[cH:19]1.[O:1]=[C:2]([NH2:3])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Br:7])[cH:8][c:9](-[c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[o:18]2)[cH:19]1)[... | Brc1cc(Br)cc(-c2nc3ccccc3o2)c1.NC(=O)OCc1ccccc1 | O=C(Nc1cc(Br)cc(-c2nc3ccccc3o2)c1)OCc1ccccc1 | 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.[Pd] | null | Heteroatom Alkylation and Arylation | Goldberg coupling | 6908f1dcf5268c746b7a7269b75335bd2fc1b14f2d985976d054ac2fda336d3a | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | O=C(Nc1cccc(-c2nc3ccccc3o2)c1)OCc1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#8:7]-[C:8](-[NH2;D1;+0:9])=[O;D1;H0:10]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:10])-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 47.3 | [{"value": 46.0, "product": "C(C1=CC=CC=C1)OC(NC1=CC(=CC(=C1)Br)C=1OC2=C(N1)C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "C(C1=CC=CC=C1)OC(NC1=CC(=CC(=C1)Br)C=1OC2=C(N1)C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 18 | HOUR | 2-(3,5-Dibromo-phenyl)-benzoxazole (0.4 g, 1.10 mmol), carbamic acid benzyl ester (0.17 g, 1.10 mmol), cesium carbonate (0.74 g, 2.30 mmol), Xantphos (46.0 mg, 0.08 mmol) and Pd(dba)2 (62.0 mg, 0.74 mmol) were placed into a dry two-neck flask, which was then flushed with nitrogen. 1,4-Dioxane (5.0 mL) was added into th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester | Carbamic ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ocnc2c1.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.[Pd] | 60 | 18 | Brc1cc(Br)cc(-c2nc3ccccc3o2)c1.NC(=O)OCc1ccccc1>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]>O=C(Nc1cc(Br)cc(-c2nc3ccccc3o2)c1)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d9107d478364f95a008861f4cb4dd11 | O=C(Nc1cc(Br)cc(-c2nc3ccccc3o2)c1)OCc1ccccc1>>Nc1cc(Br)cc(-c2nc3ccccc3o2)c1 | C(C1=CC=CC=C1)OC(NC1=CC(=CC(=C1)Br)C=1OC2=C(N1)C=CC=C2)=O.B(F)(F)F.CCOCC.CSC>>O1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)Br)N | O=C(OCc1ccccc1)[NH:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17]1>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17]1 | O=C(Nc1cc(Br)cc(-c2nc3ccccc3o2)c1)OCc1ccccc1 | Nc1cc(Br)cc(-c2nc3ccccc3o2)c1 | null | null | C(Cl)(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 92 | [{"value": 92.0, "product": "O1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)Br)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "O1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)Br)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a solution of (3-benzoxazol-2-yl-5-bromo-phenyl)-carbamic acid benzyl ester (0.160 g, 0.38 mmol) in chloroform (5.0 mL) at room temperature was added BF3-Et2O (0.21 g, 1.5 mmol) and dimethylsulfide (0.24 g, 3.78 mmol). The reaction mixture was stirred at room temperature for 20 hours. The solvent was removed and res... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)Cl | null | 20 | O=C(Nc1cc(Br)cc(-c2nc3ccccc3o2)c1)OCc1ccccc1>C(Cl)(Cl)Cl>Nc1cc(Br)cc(-c2nc3ccccc3o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-381c471eddfe4b3a8622d9272982483c | CS(=O)(=O)Cl.Nc1cc(Br)cc(-c2nc3ccccc3o2)c1>>CS(=O)(=O)Nc1cc(Br)cc(-c2nc3ccccc3o2)c1 | O1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)Br)N.CS(=O)(=O)Cl>>O1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)Br)NS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11](-[c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[cH:21]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11](-[c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[cH:21]1 | CS(=O)(=O)Cl.Nc1cc(Br)cc(-c2nc3ccccc3o2)c1 | CS(=O)(=O)Nc1cc(Br)cc(-c2nc3ccccc3o2)c1 | null | CN(C)C=1C=CN=CC1 | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(-c2nc3ccccc3o2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 55.1 | [{"value": 55.0, "product": "O1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)Br)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.1, "product": "O1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)Br)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To a solution of 3-benzoxazol-2-yl-5-bromo-phenylamine (0.12 g, 0.42 mmol) in pyridine (2.0 mL) at room temperature was added methanesulfonyl chloride (0.14 g, 1.30 mmol) and catalytic DMAP. The resulting mixture was stirred at room temperature for 17 hours. The solvent was removed under vacuum and the residue was puri... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2ocnc2c1 | HCl | CN(C)C=1C=CN=CC1.N1=CC=CC=C1 | null | 17 | CS(=O)(=O)Cl.Nc1cc(Br)cc(-c2nc3ccccc3o2)c1>CN(C)C=1C=CN=CC1.N1=CC=CC=C1>CS(=O)(=O)Nc1cc(Br)cc(-c2nc3ccccc3o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe53dbf2e3084c29a53f43c3f3606311 | Ic1cccnc1.Sc1cc(Cl)cc(Cl)c1>>Clc1cc(Cl)cc(Sc2cccnc2)c1 | C(C)(=O)OCC.IC=1C=NC=CC1.ClC=1C=C(C=C(C1)Cl)S.CC(C)([O-])C.[K+]>>ClC=1C=C(C=C(C1)Cl)SC=1C=NC=CC1 | I[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1.[Cl:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([SH:8])[cH:15]1>>[Cl:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([S:8][c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[cH:15]1 | Ic1cccnc1.Sc1cc(Cl)cc(Cl)c1 | Clc1cc(Cl)cc(Sc2cccnc2)c1 | 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].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | d40840136f5f5e29bbaef6e2996737db75662bad17302c6d6c30b714087f5e81 | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | c1ccc(Sc2cccnc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[S;H0;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | 717.1 | [{"value": 72.0, "product": "ClC=1C=C(C=C(C1)Cl)SC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 717.1, "product": "ClC=1C=C(C=C(C1)Cl)SC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A solution of 0.018 g (0.020 mmol) Pd2dba3 and 0.021 g (0.039 mmol) DPEphos in toluene (3 mL) was stirred under an argon atmosphere for 5 minutes. 3-Iodo-pyridine (0.100 g, 0.49 mmol), 3,5-dichlorobenzenethiol (0.087 g, 0.49 mmol) and 0.060 g (0.54 mmol) potassium t-butoxide were added and the reaction mixture was heat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | 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].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.C1(=CC=CC=C1)C | 100 | 2 | Ic1cccnc1.Sc1cc(Cl)cc(Cl)c1>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].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6.C1(=CC=CC=C1)C>Clc1cc(Cl)cc(Sc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-40e908d8e8294628a4cc1ff4ee50fefd | CC(=O)Nc1cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)cc(S(=O)(=O)c2cccnc2)c1>>CC(=O)Nc1cc(-c2cccc3[nH]ccc23)cc(S(=O)(=O)c2cccnc2)c1 | ClC=1C=C(C=C(C1)S(=O)(=O)C=1C=NC=CC1)NC(C)=O.N1=CC(=CC=C1)S(=O)(=O)C=1C=C(C=C(C1)C1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)NC(C)=O>>N1C=CC2=C(C=CC=C12)C=1C=C(C=C(C1)S(=O)(=O)C=1C=NC=CC1)NC(C)=O | CC(C)[Si](C(C)C)(C(C)C)[n:13]1[c:12]2[cH:11][cH:10][cH:9][c:8](-[c:7]3[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:28][c:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][cH:25][n:26][cH:27]4)[cH:17]3)[c:16]2[cH:15][cH:14]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]3[nH:13][cH:14][cH:1... | CC(=O)Nc1cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)cc(S(=O)(=O)c2cccnc2)c1 | CC(=O)Nc1cc(-c2cccc3[nH]ccc23)cc(S(=O)(=O)c2cccnc2)c1 | null | null | null | Deprotection | OtherReaction | 7c2e21594486284c07d91d3a35172f6f97c1f0e21d7ef6570d737987b23577df | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | O=S(=O)(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)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 | null | [] | null | null | null | null | N-[3-chloro-5-(pyridine-3-sulfonyl)-phenyl]-acetamide was converted to N-[3-(pyridine-3-sulfonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide and the triisopropylsilyl protecting group was removed as described in Example 35. 1H NMR (400 MHz, CD3OD): δ 9.17 (br s, 1H), 8.82 (br s, 1H), 8.38 (d, J=8.4 Hz, 1... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccncc1 | Other | null | null | null | CC(=O)Nc1cc(-c2cccc3c2ccn3[Si](C(C)C)(C(C)C)C(C)C)cc(S(=O)(=O)c2cccnc2)c1>>CC(=O)Nc1cc(-c2cccc3[nH]ccc23)cc(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b64c4dc4464f4057aa95327d0707b89a | ClCc1cccnc1.Sc1cc(Cl)cc(Cl)c1>>Clc1cc(Cl)cc(SCc2cccnc2)c1 | C(Cl)Cl.[OH-].[Na+].ClC=1C=C(C=C(C1)Cl)S.Cl.ClCC=1C=NC=CC1>>ClC=1C=C(C=C(C1)Cl)SCC=1C=NC=CC1 | Cl[CH2:9][c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1.[Cl:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([SH:8])[cH:16]1>>[Cl:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[cH:16]1 | ClCc1cccnc1.Sc1cc(Cl)cc(Cl)c1 | Clc1cc(Cl)cc(SCc2cccnc2)c1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | S-alkylation of thiols | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(SCc2cccnc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:4]:[#7;a:5]:[c:6] | 95.1 | [{"value": 95.0, "product": "ClC=1C=C(C=C(C1)Cl)SCC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "ClC=1C=C(C=C(C1)Cl)SCC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Sodium hydroxide (0.154 g. 3.85 mmol) in 2 mL water was added to 3,5-dichloro-benzenethiol (0.328 g, 1.83 mmol) in 5 mL of ethanol. After 10 min stirring, 3-chloromethyl-pyridine hydrochloride (0.301 g, 1.83 mmol) in 2 mL water was added slowly. The resulting reaction mixture was stirred at room temperature overnight. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccncc1 | HCl | O.C(C)O | null | 0.166667 | ClCc1cccnc1.Sc1cc(Cl)cc(Cl)c1>O.C(C)O>Clc1cc(Cl)cc(SCc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4582bbaa9e704aacbe4a92fcf7710903 | C=[CH][Sn]([CH2]CC)([CH2]CC)[CH2]CC.O=[N+]([O-])c1cccnc1Cl>>C=Cc1ncccc1[N+](=O)[O-] | ClC1=NC=CC=C1[N+](=O)[O-].C(CC)[Sn](C=C)(CCC)CCC>>[N+](=O)([O-])C=1C(=NC=CC1)C=C | CC[CH2][Sn]([CH2]CC)([CH2]CC)[CH:2]=[CH2:1].Cl[c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11]>>[CH2:1]=[CH:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11] | C=[CH][Sn]([CH2]CC)([CH2]CC)[CH2]CC.O=[N+]([O-])c1cccnc1Cl | C=Cc1ncccc1[N+](=O)[O-] | 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 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_vinyl | 3dd1babd20b217bb4acf07044a72bf65da3bd9404d25a4b198b8fddcb5d9092e | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccncc1 | C-C-[CH2]-[Sn](-[CH2]-C-C)(-[CH2]-C-C)-[CH;D2;+0:1]=[C;D1;H2:2].Cl-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[#7;+:7]):[c:8]>>[#7;+:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[CH;D2;+0:1]=[C;D1;H2:2]):[#7;a:4]:[c:5] | 54 | [{"value": 54.0, "product": "[N+](=O)([O-])C=1C(=NC=CC1)C=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.0, "product": "[N+](=O)([O-])C=1C(=NC=CC1)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.92 g (5.80 mmol) of 2-chloro-3-nitro-pyridine, 1.60 g (5.80 mmol) tripropyl-vinyl-stannane, 0.335 g (0.290 mmol) Pd(PPh3)4 and 10 mL of toluene were combined and refluxed under an inert atmosphere overnight. After routine aqueous workup the crude product was purified by chromatography on silica gel to gi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl.Sn | 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.C1(=CC=CC=C1)C | null | null | C=[CH][Sn]([CH2]CC)([CH2]CC)[CH2]CC.O=[N+]([O-])c1cccnc1Cl>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.C1(=CC=CC=C1)C>C=Cc1ncccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6a65ec3dd0942a3b631b6ed572f7e46 | C=Cc1ncccc1[N+](=O)[O-]>>CCc1ncccc1N | [N+](=O)([O-])C=1C(=NC=CC1)C=C>>C(C)C1=NC=CC=C1N | O=[N+:9]([O-])[c:8]1[c:3]([CH:2]=[CH2:1])[n:4][cH:5][cH:6][cH:7]1>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[NH2:9] | C=Cc1ncccc1[N+](=O)[O-] | CCc1ncccc1N | null | [Pd] | CO.C(C)(=O)OCC | Reduction | OtherReaction | 4cfc2c89a5b8ed17216485080c09efca2ccbfe28555fae72defd9e4bf408b7ae | 721ae13b9e4fcc6cfd1b6485a6bfce819c2e8b1bef3ac66e22f254a5b5eb6b97 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[CH;D2;+0:5]=[CH2;D1;+0:6]):[#7;a:7]:[c:8]>>[CH3;D1;+0:6]-[CH2;D2;+0:5]-[c:4](:[#7;a:7]:[c:8]):[c:2](-[NH2;D1;+0:1]):[c:3] | 89.1 | [{"value": 89.0, "product": "C(C)C1=NC=CC=C1N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.1, "product": "C(C)C1=NC=CC=C1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 0.220 g (1.47 mmol) of 3-nitro-2-vinyl-pyridine dissolved in 1:1 methanol/ethyl acetate was added 0.010 g of Pd/C. The resulting mixture was hydrogenated overnight at 50 psi. Filtration and removal of solvent provided 0.160 g (89% yield) of 2-ethyl-pyridin-3-ylamine.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Vinyl | Primary amine | null | null | c1ccncc1 | Other | [Pd].CO.C(C)(=O)OCC | null | 8 | C=Cc1ncccc1[N+](=O)[O-]>[Pd].CO.C(C)(=O)OCC>CCc1ncccc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f74dff4fa8a4476b2ec7430d068868b | CC(C)[Si](Oc1cc(Br)cc(Br)c1)(C(C)C)C(C)C.CCc1ncccc1N>>CCc1ncccc1Nc1cc(Br)cc(O[Si](C(C)C)(C(C)C)C(C)C)c1 | BrC=1C=C(O[Si](C(C)C)(C(C)C)C(C)C)C=C(C1)Br.C(C)C1=NC=CC=C1N>>BrC=1C=C(C=C(C1)O[Si](C(C)C)(C(C)C)C(C)C)NC=1C(=NC=CC1)CC | Br[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]([O:16][Si:17]([CH:18]([CH3:19])[CH3:20])([CH:21]([CH3:22])[CH3:23])[CH:24]([CH3:25])[CH3:26])[cH:27]1.[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[NH2:9]>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[NH:9][c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]([O:16][Si:17]([CH... | CC(C)[Si](Oc1cc(Br)cc(Br)c1)(C(C)C)C(C)C.CCc1ncccc1N | CCc1ncccc1Nc1cc(Br)cc(O[Si](C(C)C)(C(C)C)C(C)C)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].[C:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[C:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:12] | null | [] | null | null | null | null | (3,5-Dibromo-phenoxy)-triisopropyl-silane and 2-ethyl-pyridin-3-ylamine were coupled to give (3-bromo-5-triisopropylsilanyloxy-phenyl)-(2-ethyl-pyridin-3-yl)-amine as described for Example 80. (3-Bromo-5-triisopropylsilanyloxy-phenyl)-(2-ethyl-pyridin-3-yl)-amine was converted to 3-(2-ethyl-pyridin-3-ylamino)-5-(1H-ind... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | null | null | null | CC(C)[Si](Oc1cc(Br)cc(Br)c1)(C(C)C)C(C)C.CCc1ncccc1N>>CCc1ncccc1Nc1cc(Br)cc(O[Si](C(C)C)(C(C)C)C(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a0d31e72cd5419d88557d9ca46e59c5 | CN(C)c1ncccc1N.COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1>>CN(C)c1ncccc1Nc1cc(O)cc(-c2cccc3[nH]ccc23)c1 | 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.CN(C1=NC=CC=C1N)C>>CN(C1=NC=CC=C1NC=1C=C(C=C(C1)C1=C2C=CNC2=CC=C1)O)C | [CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[NH2:10].COc1ccc(C[O:14][c:13]2[cH:12][c:11](Br)[cH:26][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]4[n:22]([Si](C(C)C)(C(C)C)C(C)C)[cH:23][cH:24][c:25]34)[cH:15]2)cc1>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[NH:10][c:11]1[cH:12][c:13]([OH:14])[cH:15... | CN(C)c1ncccc1N.COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1 | CN(C)c1ncccc1Nc1cc(O)cc(-c2cccc3[nH]ccc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0216fdda3450816c545a1ee70e815d961eb4177f656896c736565a2b99cdfa38 | 00ca9e38260c521d3e1d1cbc7e1fdd484ab3843d870b2921a2ff6e0f9d2c1a8d | c1cncc(Nc2cccc(-c3cccc4[nH]ccc34)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-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].[#7:14]-[c:15](:[#7;a:16]:[c:17]):[c:18](-[NH2;D1;+0:19]):[c:20]>>[#7:14]-[c:15](:[#7;a:16]:[c:17]):[c:18](-[NH;D2;+0:19]-[c;H0;D3;+0:1]1:[c:2]:... | null | [] | null | null | null | null | Dimethyl-(3-nitro-pyridin-2-yl)-amine was obtained as a byproduct from the reaction of 2-chloro-3-nitro-pyridine with pent-4-en-1-ol (2 eq.) and sodium hydride (3 eq.) in DMF at 100° C. overnight. To this compound (0.122 g) in a mixture of ethyl acetate/methanol (5 mL, 1:1) was added 10% Pd on carbon (24 mg). The react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Primary amine.Silyl protective group | Aromatic alcohol.Secondary amine | c1ccccc1.c1ccccc1.c1cccc2[nH]ccc12 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccncc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | null | null | null | CN(C)c1ncccc1N.COc1ccc(COc2cc(Br)cc(-c3cccc4c3ccn4[Si](C(C)C)(C(C)C)C(C)C)c2)cc1>>CN(C)c1ncccc1Nc1cc(O)cc(-c2cccc3[nH]ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02f972cc0f5e4e0294a06273c791e05b | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.Nc1ccc(Br)cc1C(=O)c1cccnc1>>Nc1ccc(-c2cccc3[nH]ccc23)cc1C(=O)c1cccnc1 | C(C)(=O)OCC.NC1=C(C=C(C=C1)Br)C(=O)C=1C=NC=CC1.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+]>>NC1=C(C=C(C=C1)C1=C2C=CNC2=CC=C1)C(=O)C=1C=NC=CC1 | CC(C)[Si](C(C)C)(C(C)C)[n:11]1[c:10]2[cH:9][cH:8][cH:7][c:6](B3OC(C)(C)C(C)(C)O3)[c:14]2[cH:13][cH:12]1.Br[c:5]1[cH:4][cH:3][c:2]([NH2:1])[c:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][n:23][cH:24]2)[cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]3[nH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.Nc1ccc(Br)cc1C(=O)c1cccnc1 | Nc1ccc(-c2cccc3[nH]ccc23)cc1C(=O)c1cccnc1 | null | Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1 | O1CCOCC1.CN(C)C=O | C-C Coupling | OtherReaction | aeb86be82220e9f8efce5215aae6d0d37c29049529c0ec831bb0387e6cbe392f | 6f67b81704bc0744b740333880170d0e9a28a46a1b13bf3056e35bbffb3b7cec | O=C(c1cccnc1)c1cccc(-c2cccc3[nH]ccc23)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]2:[c:12]:1:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16]:2-B1-O-C(-C)(-C)-C(-C)(-C)-O-1>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:16]1:[c:15]:[c:14]:[c:13]:[c:12]2:[nH;D2;+0:8]:[c:9]... | null | [] | 120 | CELSIUS | null | null | To (2-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.120 g, 0.43 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (0.210 g, 0.52 mmol) in 1 mL of dioxane and 0.5 mL of DMF was added chloro(di-2-norbornylphosphino)(2′-dimethylamino-1,1′-biphenyl-2-yl)palladium (II) and 2M aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester.Silyl protective group | null | c1cccc2[nH]ccc12.B1OCCO1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccncc1 | 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.CN(C)C=O | 120 | null | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(B3OC(C)(C)C(C)(C)O3)cccc21.Nc1ccc(Br)cc1C(=O)c1cccnc1>Cl[Pd-](C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)P(C1C2CCC(C1)C2)C2C1CCC(C2)C1.O1CCOCC1.CN(C)C=O>Nc1ccc(-c2cccc3[nH]ccc23)cc1C(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-029a39d51ba24a0fbc2a74494c6e0b6d | NC(=O)c1cc(Br)cc(Br)c1.Nc1cnccn1>>NC(=O)c1cc(Br)cc(Nc2cnccn2)c1 | BrC=1C=C(C(=O)N)C=C(C1)Br.N1=C(C=NC=C1)N>>BrC=1C=C(C(=O)N)C=C(C1)NC1=NC=CN=C1 | Br[c:9]1[cH:8][c:6]([Br:7])[cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:17]1.[NH2:10][c:11]1[cH:12][n:13][cH:14][cH:15][n:16]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][c:9]([NH:10][c:11]2[cH:12][n:13][cH:14][cH:15][n:16]2)[cH:17]1 | NC(=O)c1cc(Br)cc(Br)c1.Nc1cnccn1 | NC(=O)c1cc(Br)cc(Nc2cnccn2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[N;D1;H2:5])=[O;D1;H0:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[N;D1;H2:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1):[c:7]:[c:8] | null | [] | null | null | null | null | 3,5-Dibromo-benzamide and pyrazin-2-ylamine were coupled to give 3-bromo-5-(pyrazin-2-ylamino)-benzamide as described for Example 44. 3-Bromo-5-(pyrazin-2-ylamino)-benzamide was converted to 3-(1H-indol-4-yl)-5-(pyrazin-2-ylamino)-benzamide as described in Example 75. 1H NMR (400 MHz, CDCl3): δ 10.61 (s, 1H), 8.24 (t, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnccn1 | HBr | null | null | null | NC(=O)c1cc(Br)cc(Br)c1.Nc1cnccn1>>NC(=O)c1cc(Br)cc(Nc2cnccn2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1db2cbf2f17e4343bd0566b522379ff3 | NC(=O)c1cc(Br)cc(Br)c1.Nc1cccnc1>>NC(=O)c1cc(Br)cc(Nc2cccnc2)c1 | BrC=1C=C(C(=O)N)C=C(C1)Br.N1=CC(=CC=C1)N>>BrC=1C=C(C(=O)N)C=C(C1)NC=1C=NC=CC1 | Br[c:9]1[cH:8][c:6]([Br:7])[cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:17]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[cH:17]1 | NC(=O)c1cc(Br)cc(Br)c1.Nc1cccnc1 | NC(=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](-[N;D1;H2:5])=[O;D1;H0:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14]>>[N;D1;H2:5]-[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 | 3,5-Dibromo-benzamide and pyridin-3-ylamine were coupled to give 3-bromo-5-(pyridin-3-ylamino)-benzamide as described for Example 44. 3-Bromo-5-(pyridin-3-ylamino)-benzamide was converted to 3-(1H-indol-4-yl)-5-(pyridin-3-ylamino)-benzamide as described in Example 75. 1H NMR (400 MHz, CDCl3): δ 10.58 (s, 1H), 8.36 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HBr | null | null | null | NC(=O)c1cc(Br)cc(Br)c1.Nc1cccnc1>>NC(=O)c1cc(Br)cc(Nc2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0bfeeb5b506a4595a50252d3877a08b5 | O=C(O)c1cc(Br)cc(I)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>[N-]=[N+]=NC(=O)c1cc(Br)cc(I)c1 | BrC=1C=C(C(=O)O)C=C(C1)I.C(C)(C)N(CC)C(C)C.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>BrC=1C=C(C(=O)N=[N+]=[N-])C=C(C1)I | O[C:4](=[O:5])[c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([I:12])[cH:13]1.O=P(c1ccccc1)(c1ccccc1)[N:3]=[N+:2]=[N-:1]>>[N-:1]=[N+:2]=[N:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([I:12])[cH:13]1 | O=C(O)c1cc(Br)cc(I)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | [N-]=[N+]=NC(=O)c1cc(Br)cc(I)c1 | null | null | CO | Acylation | OtherReaction | 733bf4fafd8897855b35c2a6839c7114165a830c6a4f49a25de8982866b8574d | 1caafdae684b2533c9e7294dfc2ced4755a97e34134efb3c6ff53fcade5f48fc | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=P(-[N;H0;D2;+0:6]=[#7;+:7]=[N;-;D1;H0:8])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[N;-;D1;H0:8]=[#7;+:7]=[N;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 96 | [{"value": 96.0, "product": "BrC=1C=C(C(=O)N=[N+]=[N-])C=C(C1)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.7, "product": "BrC=1C=C(C(=O)N=[N+]=[N-])C=C(C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a stirred solution of 3-bromo-5-iodo benzoic acid (5.0 g, 15 mmol) in methanol (30 mL) was added diisopropylethylamine (2.9 mL, 16.8 mmol) and diphenylphosphoryl azide (3.6 mL, 16.8 mmol). The reaction mixture was stirred for 12 hours at room temperature and then quenched with the addition of 100 mL water. A solid p... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide | Azide | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | CO | null | 12 | O=C(O)c1cc(Br)cc(I)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>CO>[N-]=[N+]=NC(=O)c1cc(Br)cc(I)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d996fc57382415498ebbc3808665e3b | COC(=O)Cl.Nc1cc(Br)cc(I)c1>>COC(=O)Nc1cc(Br)cc(I)c1 | BrC=1C=C(N)C=C(C1)I.N1=CC=CC=C1.ClC(=O)OC>>COC(NC1=CC(=CC(=C1)I)Br)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([I:12])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11]([I:12])[cH:13]1 | COC(=O)Cl.Nc1cc(Br)cc(I)c1 | COC(=O)Nc1cc(Br)cc(I)c1 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 99.2 | [{"value": 99.0, "product": "COC(NC1=CC(=CC(=C1)I)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "COC(NC1=CC(=CC(=C1)I)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a stirred solution of 3-bromo-5-iodo-aniline (0.60 g, 2.01 mmol) and pyridine (0.65 mL, 8.06 mmol) in CH2Cl2 (15 mL) at 0° C. was added methyl chloroformate (0.17 mL, 2.22 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 12 hours. The reaction mixture was washed with twice with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 12 | COC(=O)Cl.Nc1cc(Br)cc(I)c1>C(Cl)Cl>COC(=O)Nc1cc(Br)cc(I)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d665081fa7442c3a4216bae27b5bc2c | COC(=O)Nc1cc(Br)cc(I)c1.OB(O)c1cccnc1>>COC(=O)Nc1cc(Br)cc(-c2cccnc2)c1 | COC(NC1=CC(=CC(=C1)I)Br)=O.N1=CC(=CC=C1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>COC(NC1=CC(=CC(=C1)C=1C=NC=CC1)Br)=O | I[c:11]1[cH:10][c:8]([Br:9])[cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:18]1.OB(O)[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[cH:18]1 | COC(=O)Nc1cc(Br)cc(I)c1.OB(O)c1cccnc1 | COC(=O)Nc1cc(Br)cc(-c2cccnc2)c1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1):[c:2]:[c:3] | 38.3 | [{"value": 38.0, "product": "COC(NC1=CC(=CC(=C1)C=1C=NC=CC1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.3, "product": "COC(NC1=CC(=CC(=C1)C=1C=NC=CC1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | (3-Bromo-5-iodo-phenyl)-carbamic acid methyl ester (0.22 g, 0.62 mmol), 3-pyridylboronic acid (0.11 g, 0.93 mmol), and Pd(dppf)Cl2.CH2Cl2 complex (0.051 g, 0.062 mmol) were dissolved in dioxane (6 mL). Aqueous 2 M potassium carbonate (0.26 g, 1.9 mmol) was added and the reaction mixture was stirred at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HI.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1 | null | 1 | COC(=O)Nc1cc(Br)cc(I)c1.OB(O)c1cccnc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1>COC(=O)Nc1cc(Br)cc(-c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9934eafc6bc044718d676c4a1f11e389 | CCOC(=O)C1CCN(C(C)C)CC1>>CC(C)N1CCC(CO)CC1 | [OH-].[Na+].S(=O)(=O)([O-])[O-].[Mg+2].C(C)(C)N1CCC(CC1)C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)(C)N1CCC(CC1)CO | CCO[C:8]([CH:7]1[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:11][CH2:10]1)=[O:9]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[CH2:10][CH2:11]1 | CCOC(=O)C1CCN(C(C)C)CC1 | CC(C)N1CCC(CO)CC1 | null | null | O1CCCC1.O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | 105.7 | [{"value": 105.7, "product": "C(C)(C)N1CCC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -50 | CELSIUS | 2.5 | HOUR | Lithium aluminum hydride (500 mg) was suspended in 40 ml of tetrahydrofuran, a solution of 3.55 g of ethyl 1-isopropylpiperidine-4-carboxylate in 10 ml of tetrahydrofuran was added thereto at −50° C. and the mixture was stirred for 2.5 hours from under ice-cooling to at room temperature. To this were added 0.5 ml of wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | HO- | O1CCCC1.O | -50 | 2.5 | CCOC(=O)C1CCN(C(C)C)CC1>O1CCCC1.O>CC(C)N1CCC(CO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f557ff94a62c40dcb20eb8ef6d562520 | CC(C)N1CCC(CO)CC1>>CC(C)N1CCC(C=O)CC1 | C(C)(C)N1CCC(CC1)CO.C(C(=O)Cl)(=O)Cl.CS(=O)C.C(O)([O-])=O.[Na+]>>C(C)(C)N1CCC(CC1)C=O | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[CH2:10][CH2:11]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH:8]=[O:9])[CH2:10][CH2:11]1 | CC(C)N1CCC(CO)CC1 | CC(C)N1CCC(C=O)CC1 | null | null | ClCCl.O.C(C)N(CC)CC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCNCC1 | [C:1]-[C:2](-[CH2;D2;+0:3]-[OH;D1;+0:4])-[C:5]>>[C:1]-[C:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4])-[C:5] | 39.8 | [{"value": 39.8, "product": "C(C)(C)N1CCC(CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 15 | MINUTE | Oxalyl chloride (3.15 ml) was dissolved in 30 ml of dichloromethane, a solution of 3.20 ml of dimethyl sulfoxide in 6 ml of dichloromethane was added thereto at −70° C., the mixture was stirred for 15 minutes, a solution of 2.93 g of (1-isopropyl-4-piperidyl)methanol in 15 ml of dichloromethane was added thereto at −70... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC[NH]CC1 | null | ClCCl.O.C(C)N(CC)CC | -70 | 0.25 | CC(C)N1CCC(CO)CC1>ClCCl.O.C(C)N(CC)CC>CC(C)N1CCC(C=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7aa221d6ac2744a6922391cd77f30911 | BrCc1ccccc1.O=C(O)c1cccc(O)c1[N+](=O)[O-]>>O=C(OCc1ccccc1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] | OC=1C(=C(C(=O)O)C=CC1)[N+](=O)[O-].C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC=1C(=C(C(=O)OCC2=CC=CC=C2)C=CC1)[N+](=O)[O-] | Br[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.[O:1]=[C:2]([OH:3])[c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[c:24]1[N+:25](=[O:26])[O-:27]>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24]1[N+:25](=... | BrCc1ccccc1.O=C(O)c1cccc(O)c1[N+](=O)[O-] | O=C(OCc1ccccc1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 72d1c2b090053a23ad738a37a3cb5892dd40a7a11cc0ee31c0e0604d86872f07 | 6c958dcb3e552492aca64534cb11a4afa104129654bdbddfbe6a577b0564c983 | O=C(OCc1ccccc1)c1cccc(OCc2ccccc2)c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[O;D1;H0:5]=[C:6](-[O;H0;D2;+0:7]-[C:13]-[c:14])-[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12] | null | [] | null | null | null | null | 3-Hydroxy-2-nitrobenzoic acid (10.5 g) was dissolved in 60 ml of N,N-dimethylformamide, then 15 ml of benzyl bromide and 19.0 g of potassium carbonate were added at 0° C. and the mixture was stirred at room temperature for one night. The reaction solution was filtered through Celite and the filtrate was concentrated in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Aromatic alcohol | Ester.Ether | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Br- | CN(C=O)C | null | null | BrCc1ccccc1.O=C(O)c1cccc(O)c1[N+](=O)[O-]>CN(C=O)C>O=C(OCc1ccccc1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e5fe57f3f7d4301a11ddaebb78ff923 | O=C(OCc1ccccc1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-]>>O=C(O)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] | C(C1=CC=CC=C1)OC=1C(=C(C(=O)OCC2=CC=CC=C2)C=CC1)[N+](=O)[O-].[OH-].[Na+]>>C(C1=CC=CC=C1)OC=1C(=C(C(=O)O)C=CC1)[N+](=O)[O-] | c1ccc(C[O:3][C:2](=[O:1])[c:4]2[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]2[N+:18](=[O:19])[O-:20])cc1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]1[N+:18](=[O:19])[O-:20] | O=C(OCc1ccccc1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] | O=C(O)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccccc2)cc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | 101.5 | [{"value": 101.5, "product": "C(C1=CC=CC=C1)OC=1C(=C(C(=O)O)C=CC1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 5 | HOUR | To 20.7 g of benzyl 3-benzyloxy-2-nitrobenzoate were added 100 ml of ethanol and 120 ml of a 1N aqueous solution of sodium hydroxide and the mixture was stirred at room temperature for one night, at 60° C. for 3 hours and at 80° C. for 5 hours. After ethanol was evaporated in vacuo, the resulting aqueous solution was w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | C(C)O | 80 | 5 | O=C(OCc1ccccc1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-]>C(C)O>O=C(O)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b6610d6df3b4e849f97afc52e3fd0e9 | O=C(Nc1ccc(Cl)cn1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-]>>Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1 | C(C1=CC=CC=C1)OC=1C(=C(C(=O)NC2=NC=C(C=C2)Cl)C=CC1)[N+](=O)[O-].CC=1C(=C(C(=C(C1)C)C)C)C>>NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=CC=C1O | O=[N+:1]([O-])[c:2]1[c:3]([O:4]Cc2ccccc2)[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1>>[NH2:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1 | O=C(Nc1ccc(Cl)cn1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] | Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 9170d0c986a4b23b0014d38a47c7fc9d4706242a2267d3f5bc0d6f66b2394435 | f6fedbf3f30216a140de5c3218dc044b3cb8996afe756cfb2650e812e7cf56ad | O=C(Nc1ccccn1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[O;H0;D2;+0:8]-C-c1:c:c:c:c:c:1):[c:9]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2](-[NH2;D1;+0:1]):[c:7](-[OH;D1;+0:8]):[c:9] | 89.6 | [{"value": 89.6, "product": "NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=CC=C1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | To 7.44 g of 3-benzyloxy-N-(5-chloro-2-pyridyl)-2-nitrobenzamide were added 40 ml of trifluoroacetic acid and 3.72 g of pentamethylbenzene and the mixture was stirred at 40° C. for one night. The reaction solution was concentrated in vacuo, to the residue was added a saturated aqueous solution of sodium hydrogen carbon... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group | Aromatic alcohol.Primary amine | c1ccccc1 | null | c1ccccc1.c1ccncc1 | HO- | FC(C(=O)O)(F)F | 40 | null | O=C(Nc1ccc(Cl)cn1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-]>FC(C(=O)O)(F)F>Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30fbaf5ebfbe45d680c9c4ab79a3bf84 | Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1.O=C1CCC(=O)N1Cl>>Nc1c(O)cc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=CC=C1O.ClN1C(CCC1=O)=O>>NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=C(C=C1O)Cl | [NH2:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1.O=C1CCC(=O)N1[Cl:7]>>[NH2:1][c:2]1[c:3]([OH:4])[cH:5][c:6]([Cl:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1 | Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1.O=C1CCC(=O)N1Cl | Nc1c(O)cc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | null | null | CN(C=O)C | Functional Group Interconversion | Chlorination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(Nc1ccccn1)c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c;H0;D3;+0:7](-[Cl;H0;D1;+0:1]):[c:8]:[c:9] | 22.2 | [{"value": 22.2, "product": "NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=C(C=C1O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 4 | HOUR | 2-Amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (3.06 g) and 1.80 g of N-chlorosuccinimide were dissolved in 60 ml of N,N-dimethylformamide, the solution was stirred at 50° C. for 8 hours and at room temperature for 4 hours and the insoluble matter was filtered off. The solvent was evaporated in vacuo, to the resulti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | CN(C=O)C | 50 | 4 | Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1.O=C1CCC(=O)N1Cl>CN(C=O)C>Nc1c(O)cc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf54cf6e6afe4726b96c5a998dd415b6 | Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1.O=C1CCC(=O)N1Br>>Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1 | NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=CC=C1O.BrN1C(CCC1=O)=O.O.C(C)(=O)OCC.BrN1C(CCC1=O)=O>>NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=C(C=C1O)Br | [NH2:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1.O=C1CCC(=O)N1[Br:7]>>[NH2:1][c:2]1[c:3]([OH:4])[cH:5][c:6]([Br:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1 | Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1.O=C1CCC(=O)N1Br | Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(Nc1ccccn1)c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c;H0;D3;+0:7](-[Br;H0;D1;+0:1]):[c:8]:[c:9] | 83.3 | [{"value": 83.3, "product": "NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=C(C=C1O)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | null | null | 2-Amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (5.27 g) was dissolved in 60 ml of N,N-dimethylformamide and the solution was stirred at −15° C. N-Bromosuccinimide (3.56 g) was added thereto by dividing into four with an interval of 5 minutes each and the mixture was stirred at −15° C. for 1.5 hours. Then more 0.36 g... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | CN(C=O)C | -15 | null | Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1.O=C1CCC(=O)N1Br>CN(C=O)C>Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4cfcc01f8e9d4cd8be424b588c6114d4 | Nc1ccc(Cl)cc1.O=C(O)c1cccc(O)c1[N+](=O)[O-]>>O=C(Nc1ccc(Cl)cc1)c1cccc(O)c1[N+](=O)[O-] | OC=1C(=C(C(=O)O)C=CC1)[N+](=O)[O-].ClC1=CC=C(N)C=C1.Cl.C(C)N=C=NCCCN(C)C.ON1N=NC2=C1C=CC=C2>>ClC1=CC=C(NC(C2=C(C(=CC=C2)O)[N+](=O)[O-])=O)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[c:17]1[N+:18](=[O:19])[O-:20]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[c:17]1[N+:18](=[O:19])[O-:20] | Nc1ccc(Cl)cc1.O=C(O)c1cccc(O)c1[N+](=O)[O-] | O=C(Nc1ccc(Cl)cc1)c1cccc(O)c1[N+](=O)[O-] | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 92.9 | [{"value": 92.9, "product": "ClC1=CC=C(NC(C2=C(C(=CC=C2)O)[N+](=O)[O-])=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | 3-Hydroxy-2-nitrobenzoic acid (2.00 g) was dissolved in 110 ml of N,N-dimethylformamide, then 1.53 g of 4-chloroaniline, 3.15 g of 1-ethyl-3-[3-(N,N-dimethylamino) propyl]carbodiimide hydrochloride and 2.21 g of 1-hydroxybenzotriazole were added thereto and the mixture was stirred at room temperature for 4 days. The re... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | 96 | Nc1ccc(Cl)cc1.O=C(O)c1cccc(O)c1[N+](=O)[O-]>CN(C=O)C>O=C(Nc1ccc(Cl)cc1)c1cccc(O)c1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65a38d3fa3914cd8a6e03e67d37dd0f5 | O=C(Nc1ccc(Br)cn1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-]>>O=C(Nc1ccc(Br)cn1)c1cccc(O)c1[N+](=O)[O-] | C(C1=CC=CC=C1)OC=1C(=C(C(=O)NC2=NC=C(C=C2)Br)C=CC1)[N+](=O)[O-].CC=1C(=C(C(=C(C1)C)C)C)C>>BrC=1C=CC(=NC1)NC(C1=C(C(=CC=C1)O)[N+](=O)[O-])=O | c1ccc(C[O:16][c:15]2[cH:14][cH:13][cH:12][c:11]([C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]3)[c:17]2[N+:18](=[O:19])[O-:20])cc1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1)[c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[c:17]1[N+:18](=[O:19])[O-:20] | O=C(Nc1ccc(Br)cn1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-] | O=C(Nc1ccc(Br)cn1)c1cccc(O)c1[N+](=O)[O-] | null | null | FC(C(=O)O)(F)F | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Nc1ccccn1)c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 93 | [{"value": 93.0, "product": "BrC=1C=CC(=NC1)NC(C1=C(C(=CC=C1)O)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To 10.7 g of 3-benzyloxy-N-(5-bromo-2-pyridyl)-2-nitrobenzamide were added 50 ml of trifluoroacetic acid and 4.88 g of pentamethylbenzene and the mixture was stirred at room temperature for 4 days. The reaction solution was concentrated in vacuo, to the residue was added a saturated aqueous solution of sodium hydrogen ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccncc1.c1ccccc1 | Other | FC(C(=O)O)(F)F | null | 96 | O=C(Nc1ccc(Br)cn1)c1cccc(OCc2ccccc2)c1[N+](=O)[O-]>FC(C(=O)O)(F)F>O=C(Nc1ccc(Br)cn1)c1cccc(O)c1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9af9e730d78f44cdbede39e3d67e7fb3 | O=C(Nc1ccc(Br)cn1)c1cccc(O)c1[N+](=O)[O-]>>Nc1c(O)cccc1C(=O)Nc1ccc(Br)cn1 | [Cl-].[NH4+].BrC=1C=CC(=NC1)NC(C1=C(C(=CC=C1)O)[N+](=O)[O-])=O>>NC1=C(C(=O)NC2=NC=C(C=C2)Br)C=CC=C1O | O=[N+:1]([O-])[c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]1>>[NH2:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]1 | O=C(Nc1ccc(Br)cn1)c1cccc(O)c1[N+](=O)[O-] | Nc1c(O)cccc1C(=O)Nc1ccc(Br)cn1 | null | null | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccn1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#7:6])=[O;D1;H0:7]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 6 | [{"value": 6.0, "product": "NC1=C(C(=O)NC2=NC=C(C=C2)Br)C=CC=C1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-(5-Bromo-2-pyridyl)-3-hydroxy-2-nitrobenzamide (7.71 g) was suspended in 50 ml of ethanol and 22 ml of distilled water, then 12.7 g of reduced iron and 2.45 g of ammonium chloride were added thereto and the mixture was heated to reflux for 6 hours. After it was cooled down to room temperature, insoluble matter was fi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | O.C(C)O | null | null | O=C(Nc1ccc(Br)cn1)c1cccc(O)c1[N+](=O)[O-]>O.C(C)O>Nc1c(O)cccc1C(=O)Nc1ccc(Br)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b1ce6b5af8745e2a725956aee0de433 | Nc1c(O)cccc1C(=O)Nc1ccc(Br)cn1.O=C1CCC(=O)N1Cl>>Nc1c(O)cc(Cl)cc1C(=O)Nc1ccc(Br)cn1 | NC1=C(C(=O)NC2=NC=C(C=C2)Br)C=CC=C1O.ClN1C(CCC1=O)=O>>NC1=C(C(=O)NC2=NC=C(C=C2)Br)C=C(C=C1O)Cl | [NH2:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][n:19]1.O=C1CCC(=O)N1[Cl:7]>>[NH2:1][c:2]1[c:3]([OH:4])[cH:5][c:6]([Cl:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][n:19]1 | Nc1c(O)cccc1C(=O)Nc1ccc(Br)cn1.O=C1CCC(=O)N1Cl | Nc1c(O)cc(Cl)cc1C(=O)Nc1ccc(Br)cn1 | null | null | CN(C=O)C | Functional Group Interconversion | Chlorination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(Nc1ccccn1)c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c;H0;D3;+0:7](-[Cl;H0;D1;+0:1]):[c:8]:[c:9] | 50.6 | [{"value": 50.6, "product": "NC1=C(C(=O)NC2=NC=C(C=C2)Br)C=C(C=C1O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | 2-Amino-N-(5-bromo-2-pyridyl)-3-hydroxybenzamide (1.99 g) and 990 mg of N-chlorosuccinimide were dissolved in 30 ml of N,N-dimethylformamide, the solution was stirred at 50° C. for 2 hours and the insoluble matter was filtered off. The solvent was evaporated in vacuo, water was added to the resulting residue and the pr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | CN(C=O)C | 50 | 2 | Nc1c(O)cccc1C(=O)Nc1ccc(Br)cn1.O=C1CCC(=O)N1Cl>CN(C=O)C>Nc1c(O)cc(Cl)cc1C(=O)Nc1ccc(Br)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6b5cc335d7c487e830aad2e34cfe502 | CC(C)N1CCC(C(=O)O)CC1.Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1>>CC(C)N1CCC(C(=O)Nc2c(O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1 | NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=C(C=C1O)Br.C(C)(C)N1CCC(CC1)C(=O)O.C([O-])(O)=O.[Na+].Cl.C(C)N=C=NCCCN(C)C.ON1N=NC2=C1C=CC=C2>>BrC1=CC(=C(NC(=O)C2CCN(CC2)C(C)C)C(=C1)O)C(NC1=NC=C(C=C1)Cl)=O | O[C:8]([CH:7]1[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:30][CH2:29]1)=[O:9].[NH2:10][c:11]1[c:12]([OH:13])[cH:14][c:15]([Br:16])[cH:17][c:18]1[C:19](=[O:20])[NH:21][c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][n:28]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([C:8](=[O:9])[NH:10][c:11]2[c:12]([OH:13])[cH:14]... | CC(C)N1CCC(C(=O)O)CC1.Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1 | CC(C)N1CCC(C(=O)Nc2c(O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1NC(=O)C1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12] | 59.3 | [{"value": 59.3, "product": "BrC1=CC(=C(NC(=O)C2CCN(CC2)C(C)C)C(=C1)O)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 46 | HOUR | 2-Amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (5.14 g) and 2.83 g of 1-isopropylpiperidine-4-carboxylic acid were dissolved in 75 ml of N,N-dimethylformamide, then 4.33 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride and 3.04 g of 1-hydroxybenzotriazole were added thereto and the mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 46 | CC(C)N1CCC(C(=O)O)CC1.Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1>CN(C=O)C.C(C)(=O)OCC>CC(C)N1CCC(C(=O)Nc2c(O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5d779f62c794173830e4dd98530e123 | CC(C)N1CCC(C=O)CC1.Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1>>CC(C)N1CCC(CNc2c(O)cccc2C(=O)Nc2ccc(Cl)cn2)CC1.Cl | O.NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=CC=C1O.C(C)(C)N1CCC(CC1)C=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>Cl.ClC=1C=CC(=NC1)NC(C1=C(C(=CC=C1)O)NCC1CCN(CC1)C(C)C)=O | O=[CH:8][CH:7]1[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:28][CH2:27]1.[NH2:9][c:10]1[c:11]([OH:12])[cH:13][cH:14][cH:15][c:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][c:10]2[c:11]([OH:12])[cH:13][cH:14][cH:15][c:16]2[... | CC(C)N1CCC(C=O)CC1.Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1 | CC(C)N1CCC(CNc2c(O)cccc2C(=O)Nc2ccc(Cl)cn2)CC1.Cl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Reductive amination with aldehyde | 7d1b6092237fd369773eab744edec53855841c9fba6370f9ea667d17afb10a43 | 349d032a341f28a5e8c653eea4b45ad75ec46e02d142d0018cfaf68db09826d4 | O=C(Nc1ccccn1)c1ccccc1NCC1CCNCC1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):[c:11] | 122.4 | [{"value": 122.4, "product": "Cl.ClC=1C=CC(=NC1)NC(C1=C(C(=CC=C1)O)NCC1CCN(CC1)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 15 | HOUR | 2-Amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (100 mg) and 80 mg of 1-isopropylpiperidine-4-carbaldehyde were suspended in 5 ml of toluene, then 10 mg of p-toluenesulfonic acid hydrate were added thereto and the mixture was heated to reflux for 2 hours together with removal of water by an azeotropic operation. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | null | C1(=CC=CC=C1)C | 70 | 15 | CC(C)N1CCC(C=O)CC1.Nc1c(O)cccc1C(=O)Nc1ccc(Cl)cn1>C1(=CC=CC=C1)C>CC(C)N1CCC(CNc2c(O)cccc2C(=O)Nc2ccc(Cl)cn2)CC1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29078b7230a741bf84969d79b6bf9c90 | O=C(Nc1ccc(Cl)cc1)c1cccc(O)c1[N+](=O)[O-].[NH4+]>>CC(C)N1CCC(CNc2c(O)cccc2C(=O)Nc2ccc(Cl)cc2)CC1.N | O.[Cl-].[NH4+].ClC1=CC=C(NC(C2=C(C(=CC=C2)O)[N+](=O)[O-])=O)C=C1>>N.ClC1=CC=C(NC(C2=C(C(=CC=C2)O)NCC2CCN(CC2)C(C)C)=O)C=C1 | O=[N+:9]([O-])[c:10]1[c:11]([OH:12])[cH:13][cH:14][cH:15][c:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][cH:1][c:23]([Cl:24])[cH:25][cH:26]1.[NH4+:4]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][c:10]2[c:11]([OH:12])[cH:13][cH:14][cH:15][c:16]2[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH... | O=C(Nc1ccc(Cl)cc1)c1cccc(O)c1[N+](=O)[O-].[NH4+] | CC(C)N1CCC(CNc2c(O)cccc2C(=O)Nc2ccc(Cl)cc2)CC1.N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | cb96696a59fa22d7baa55967dcf7a7dd9eebf221a0c45c5d4249830ddbe6cd51 | 8ec145831198165a0e3de2c65ce2d1ca99f9fce2dfea73b866ca077d579a0d30 | O=C(Nc1ccccc1)c1ccccc1NCC1CCNCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[Cl;D1;H0:12]):[cH;D2;+0:13]:[cH;D2;+0:14]:1.[NH4+;D0:15]>>[C;D1;H3:16]-[C:17](-[CH3;D1;+0:13])-[N;H0;D3;+0:15]1-[C:18]-[C:19]-[C:20](-[C:21]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]2:[c:9]... | null | [] | 60 | CELSIUS | 2 | HOUR | 4′-Chloro-3-hydroxy-2-nitrobenzanilide (1.43 g) was suspended in 50 ml of methanol, then 5 ml of distilled water, 2.80 g of reduced iron and 530 mg of ammonium chloride were added thereto and the mixture was stirred at 60° C. for 2 hours. The reaction was filtered through Celite and concentrated in vacuo. To the result... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Aromatic halide.Secondary amine.Tertiary amine | c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1 | null | CO | 60 | 2 | O=C(Nc1ccc(Cl)cc1)c1cccc(O)c1[N+](=O)[O-].[NH4+]>CO>CC(C)N1CCC(CNc2c(O)cccc2C(=O)Nc2ccc(Cl)cc2)CC1.N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7e9fbe4f20a4ac4afc9bb11f2d35b06 | CC(C)N1CCC(C(=O)O)CC1.Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1>>CC(C)N1CCC(C(=O)Nc2c(O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1 | NC1=C(C(=O)NC2=NC=C(C=C2)Cl)C=C(C=C1O)Br.C(C)(C)N1CCC(CC1)C(=O)O.Cl.C(C)N=C=NCCCN(C)C.ON1N=NC2=C1C=CC=C2>>Cl.BrC1=CC(=C(NC(=O)C2CCN(CC2)C(C)C)C(=C1)O)C(NC1=NC=C(C=C1)Cl)=O | O[C:8]([CH:7]1[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:30][CH2:29]1)=[O:9].[NH2:10][c:11]1[c:12]([OH:13])[cH:14][c:15]([Br:16])[cH:17][c:18]1[C:19](=[O:20])[NH:21][c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][n:28]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([C:8](=[O:9])[NH:10][c:11]2[c:12]([OH:13])[cH:14]... | CC(C)N1CCC(C(=O)O)CC1.Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1 | CC(C)N1CCC(C(=O)Nc2c(O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1 | null | null | O.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1NC(=O)C1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12] | 72.7 | [{"value": 72.7, "product": "Cl.BrC1=CC(=C(NC(=O)C2CCN(CC2)C(C)C)C(=C1)O)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | 2-Amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (2.39 g) and 1.32 g of 1-isopropylpiperidine-4-carboxylic acid were dissolved in 35 ml of N,N-dimethylformamide, then 2.02 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride, 1.42 g of 1-hydroxybenzotriazole and 1.46 ml of triethylamine were added ther... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | 22 | CC(C)N1CCC(C(=O)O)CC1.Nc1c(O)cc(Br)cc1C(=O)Nc1ccc(Cl)cn1>O.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>CC(C)N1CCC(C(=O)Nc2c(O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09d8927eed9d4206824edc5084cae123 | CNC(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1>>CNC(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | C(Cl)Cl.CO.NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)S.CNC(CBr)=O.C(=O)(O)[O-].[Na+]>>NC1=C(C(=C(C(=N1)SCC(=O)NC)C#N)C1=CC=C(C=C1)O)C#N | Br[CH2:5][C:3]([NH:2][CH3:1])=[O:4].[SH:6][c:7]1[n:8][c:9]([NH2:10])[c:11]([C:12]#[N:13])[c:14](-[c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]2)[c:22]1[C:23]#[N:24]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][S:6][c:7]1[n:8][c:9]([NH2:10])[c:11]([C:12]#[N:13])[c:14](-[c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]2)[c:2... | CNC(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1 | CNC(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | null | null | O.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C;D1;H3:5].[SH;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[C;D1;H3:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10] | null | [] | null | null | null | null | At room temperature (RT), 53.6 mg (0.2 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile and 45.6 mg (0.3 mmol) of N-methylbromo-acetamide are stirred in 0.5 ml of dimethylformamide (DMF) together with 33.6 mg (0.4 mmol) of NaHCO3 for 4 hours. Thin-layer chromatography (TLC) (CH2Cl2/CH3OH 10:1)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccccc1 | HBr | O.CN(C=O)C.C(C)(=O)OCC | null | null | CNC(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1>O.CN(C=O)C.C(C)(=O)OCC>CNC(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64b645d960d245bb88cbc3c5b421da9c | CCN(CC)C(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1>>CCN(CC)C(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | C(Cl)Cl.CO.NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)S.C(C)N(C(CBr)=O)CC.C(=O)(O)[O-].[Na+]>>NC1=C(C(=C(C(=N1)SCC(=O)N(CC)CC)C#N)C1=CC=C(C=C1)O)C#N | Br[CH2:8][C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7].[SH:9][c:10]1[n:11][c:12]([NH2:13])[c:14]([C:15]#[N:16])[c:17](-[c:18]2[cH:19][cH:20][c:21]([OH:22])[cH:23][cH:24]2)[c:25]1[C:26]#[N:27]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[CH2:8][S:9][c:10]1[n:11][c:12]([NH2:13])[c:14]([C:15]#[N:16])[c:17](-[c:18]... | CCN(CC)C(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1 | CCN(CC)C(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | null | null | O.CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[SH;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C:5]-[#7:4](-[C:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11] | null | [] | null | null | null | null | At RT, 53.6 mg (0.2 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile and 58.2 mg (0.3 mmol) of N,N-diethylbromoacetamide are stirred in 0.5 ml of DMF together with 33.6 mg (0.4 mmol) of NaHCO3 for 4 hours. TLC (CH2Cl2/CH3OH 10:1) shows complete conversion. The entire mixture is diluted with wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccccc1 | HBr | O.CN(C)C=O.C(C)(=O)OCC | null | null | CCN(CC)C(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1>O.CN(C)C=O.C(C)(=O)OCC>CCN(CC)C(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78fedb32620646d5b1f94b66e481d520 | CCNC(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1>>CCNC(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)S.C(C)NC(CBr)=O.C(=O)(O)[O-].[Na+]>>NC1=C(C(=C(C(=N1)SCC(=O)NCC)C#N)C1=CC=C(C=C1)O)C#N | Br[CH2:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5].[SH:7][c:8]1[n:9][c:10]([NH2:11])[c:12]([C:13]#[N:14])[c:15](-[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[c:23]1[C:24]#[N:25]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][S:7][c:8]1[n:9][c:10]([NH2:11])[c:12]([C:13]#[N:14])[c:15](-[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:... | CCNC(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1 | CCNC(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5].[SH;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[C:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10] | null | [] | null | null | null | null | At RT 0.76 g (2 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile and 0.5 g (3 mmol) of N-ethylbromoacetamide are stirred in 5 ml of DMF together with 0.34 g (4 mmol) of NaHCO3 for 4 hours. After dilution with water, the mixture is extracted with ethyl acetate and the ethyl acetate phase is dri... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | null | null | CCNC(=O)CBr.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1>CN(C)C=O>CCNC(=O)CSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-505786e9f22b4e2dad9573f0558735e5 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1.NCCBr>>N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1 | NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)S.Br.BrCCN.C(=O)(O)[O-].[Na+]>>NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)SCCN | [N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([SH:8])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]1.Br[CH2:9][CH2:10][NH2:11]>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][CH2:10][NH2:11])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]1 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1.NCCBr | N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1 | null | null | Cl.CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[N;D1;H2:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[N;D1;H2:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | null | null | 268 mg (1 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile, 105 mg (1 mmol) of 2-bromoethylamine hydrobromide and 168 mg (2 mmol) of NaHCO3 are stirred in 1 ml of DMF for 1 hour. The entire mixture is diluted with a few milliliters of 1N HCl. The crystals are filtered off with suction and drie... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccccc1 | HBr | Cl.CN(C)C=O | null | null | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1.NCCBr>Cl.CN(C)C=O>N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-671ec931b8ea43fb8cbdaf938cb5a441 | CC(=O)n1ccnc1.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>>CC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)SCCN.C(C)(=O)N1C=NC=C1.O>>NC1=C(C(=C(C(=N1)SCCNC(C)=O)C#N)C1=CC=C(C=C1)O)C#N | c1cn([C:2]([CH3:1])=[O:3])cn1.[NH2:4][CH2:5][CH2:6][S:7][c:8]1[n:9][c:10]([NH2:11])[c:12]([C:13]#[N:14])[c:15](-[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[c:23]1[C:24]#[N:25]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][S:7][c:8]1[n:9][c:10]([NH2:11])[c:12]([C:13]#[N:14])[c:15](-[c:16]2[cH:17][cH:18][c:19]([OH:2... | CC(=O)n1ccnc1.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1 | CC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | null | null | CN(C)C=O | Acylation | OtherReaction | f4659f3a15ccf79ef925dffc68bd610eae9f8ffbe31464b66bb78c4334a7ca96 | 45ca336cc0b18cf59a837ab710e8845f67d23306b24bf1f37b36a34a2de4779a | c1ccc(-c2ccncc2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-n1:c:c:n:c:1.[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:2](-[C;D1;H3:1])=[O;D1;H0:3] | null | [] | null | null | 5 | HOUR | At RT 60 mg (0.2 mmol) of 2-amino-6-[(2-aminoethyl)sulfanyl]-4-(4-hydroxyphenyl)-3,5-pyridinedicarbonitrile and 30 mg (0.3 mmol) of N-acetylimidazole are stirred in 0.5 ml of DMF for 1 hour. Water is slowly added dropwise, the mixture becomes slightly turbid and the crude product crystallizes out. The product is filter... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | c1c[nH]cn1 | null | c1ccncc1.c1ccccc1 | Other | CN(C)C=O | null | 5 | CC(=O)n1ccnc1.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>CN(C)C=O>CC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a1fad36eb70425982c51764c2b086a9 | N#C[O-].N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>>N#Cc1c(N)nc(SCCNC(N)=O)c(C#N)c1-c1ccc(O)cc1 | NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)SCCN.[O-]C#N.[K+]>>NC1=C(C(=C(C(=N1)SCCNC(=O)N)C#N)C1=CC=C(C=C1)O)C#N | [C:12](#[N:13])[O-:14].[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][CH2:10][NH2:11])[c:15]([C:16]#[N:17])[c:18]1-[c:19]1[cH:20][cH:21][c:22]([OH:23])[cH:24][cH:25]1>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][CH2:10][NH:11][C:12]([NH2:13])=[O:14])[c:15]([C:16]#[N:17])[c:18]1-[c:19]1[cH:20][cH:21][... | N#C[O-].N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1 | N#Cc1c(N)nc(SCCNC(N)=O)c(C#N)c1-c1ccc(O)cc1 | null | CO | Cl | Acylation | OtherReaction | f8798d1193af6f9b314ac8855e814716b90ff3758bcfa29778cc632fcaa83b7a | 5efe06db19c806d9e9798893351dc14c0cc48f1e8f8c857f54c6171e86c96a1b | c1ccc(-c2ccncc2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[O-;H0;D1:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](-[NH2;D1;+0:4])=[O;H0;D1;+0:6] | null | [] | 50 | CELSIUS | 10 | HOUR | 31.1 mg (0.1 mmol) of 2-amino-6-[(2-aminoethyl)sulfanyl]-4-(4-hydroxyphenyl)-3,5-pyridinedicarbonitrile are suspended in 0.91 ml of 1N HCl, and 8.1 mg (0.1 mmol) of potassium cyanate are added. After the addition of a few drops of methanol, the mixture is stirred at 50° C. for a total of 10 hours. The crystals are filt... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Urea | null | null | c1ccncc1.c1ccccc1 | null | CO.Cl | 50 | 10 | N#C[O-].N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>CO.Cl>N#Cc1c(N)nc(SCCNC(N)=O)c(C#N)c1-c1ccc(O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-257949194b88492588089f2d1031feb9 | CN=C=O.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>>CNC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)SCCN.CN=C=O>>NC1=C(C(=C(C(=N1)SCCNC(=O)NC)C#N)C1=CC=C(C=C1)O)C#N | [CH3:1][N:2]=[C:3]=[O:4].[NH2:5][CH2:6][CH2:7][S:8][c:9]1[n:10][c:11]([NH2:12])[c:13]([C:14]#[N:15])[c:16](-[c:17]2[cH:18][cH:19][c:20]([OH:21])[cH:22][cH:23]2)[c:24]1[C:25]#[N:26]>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[n:10][c:11]([NH2:12])[c:13]([C:14]#[N:15])[c:16](-[c:17]2[cH:18][cH:19][c:20]([O... | CN=C=O.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1 | CNC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2ccncc2)cc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[C;D1;H3:1] | null | [] | null | null | 8 | HOUR | 62.2 mg (0.2 mmol) of 2-amino-6-[(2-aminoethyl)sulfanyl]-4-(4-hydroxyphenyl)-3,5-pyridinedicarbonitrile are suspended in 0.4 ml of DMF, and 11.4 mg (0.2 mmol) of methyl isocyanate are added at room temperature. The mixture is stirred overnight, filtered and purified by preparative HPLC.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccncc1.c1ccccc1 | null | CN(C)C=O | null | 8 | CN=C=O.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>CN(C)C=O>CNC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc5e0ee4c1fd4e79a84df5f3682c463b | CCN=C=O.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>>CNC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)SCCN.C(C)N=C=O>>NC1=C(C(=C(C(=N1)SCCNC(=O)NC)C#N)C1=CC=C(C=C1)O)C#N | C[CH2:1][N:2]=[C:3]=[O:4].[NH2:5][CH2:6][CH2:7][S:8][c:9]1[n:10][c:11]([NH2:12])[c:13]([C:14]#[N:15])[c:16](-[c:17]2[cH:18][cH:19][c:20]([OH:21])[cH:22][cH:23]2)[c:24]1[C:25]#[N:26]>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[n:10][c:11]([NH2:12])[c:13]([C:14]#[N:15])[c:16](-[c:17]2[cH:18][cH:19][c:20]([... | CCN=C=O.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1 | CNC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N | null | null | CN(C)C=O | Acylation | OtherReaction | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2ccncc2)cc1 | C-[CH2;D2;+0:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[CH3;D1;+0:1] | null | [] | null | null | 8 | HOUR | 62.2 mg (0.2 mmol) of 2-amino-6-[(2-aminoethyl)sulfanyl]-4-(4-hydroxyphenyl)-3,5-pyridinedicarbonitrile are suspended in 0.4 ml of DMF, and 14.2 mg (0.2 mmol) of ethyl isocyanate are added at room temperature. The mixture is stirred overnight, filtered and purified by preparative HPLC.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccncc1.c1ccccc1 | Other | CN(C)C=O | null | 8 | CCN=C=O.N#Cc1c(N)nc(SCCN)c(C#N)c1-c1ccc(O)cc1>CN(C)C=O>CNC(=O)NCCSc1nc(N)c(C#N)c(-c2ccc(O)cc2)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5cc5fc8c6e2e422f8d848b9f531ad563 | N#Cc1c(N)nc(S)c(C#N)c1-c1cc(Cl)c(O)c(Cl)c1.NC(=O)CBr>>N#Cc1c(N)nc(CC(N)=O)c(C#N)c1-c1cc(Cl)c(O)c(Cl)c1 | NC1=NC(=C(C(=C1C#N)C1=CC(=C(C(=C1)Cl)O)Cl)C#N)S.BrCC(=O)N.C(=O)(O)[O-].[Na+]>>C(#N)C=1C(=NC(=C(C1C1=CC(=C(C(=C1)Cl)O)Cl)C#N)N)CC(N)=O | S[c:7]1[n:6][c:4]([NH2:5])[c:3]([C:2]#[N:1])[c:15](-[c:16]2[cH:17][c:18]([Cl:19])[c:20]([OH:21])[c:22]([Cl:23])[cH:24]2)[c:12]1[C:13]#[N:14].Br[CH2:8][C:9]([NH2:10])=[O:11]>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([CH2:8][C:9]([NH2:10])=[O:11])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][c:18]([Cl:19])[c:20]([OH:21])[... | N#Cc1c(N)nc(S)c(C#N)c1-c1cc(Cl)c(O)c(Cl)c1.NC(=O)CBr | N#Cc1c(N)nc(CC(N)=O)c(C#N)c1-c1cc(Cl)c(O)c(Cl)c1 | null | null | O.CN(C)C=O | C-C Coupling | OtherReaction | 6852ba785294b64b22dacb73c7c061e0926b672b30f5e7866280494a7400960e | 76a52a34f99aab8d142e9d5af88822c401475fcc21e1f295efc28ca49de2a52f | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].S-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:8](-[C:9]#[N;D1;H0:10]):[c:11]>>[N;D1;H0:10]#[C:9]-[c:8](:[c:11]):[c;H0;D3;+0:5](-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4]):[#7;a:6]:[c:7] | null | [] | null | null | 8 | HOUR | 337.2 mg (1 mmol) of 2-amino-4-(3,5-dichloro-4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile and 207 mg (1.5 mmol) of bromoacetamide are dissolved in 4 ml of DMF, 336 mg (4 mmol) of NaHCO3 are added and the mixture is stirred at RT for 8 hours. The mixture is diluted with water and washed with ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | null | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | O.CN(C)C=O | null | 8 | N#Cc1c(N)nc(S)c(C#N)c1-c1cc(Cl)c(O)c(Cl)c1.NC(=O)CBr>O.CN(C)C=O>N#Cc1c(N)nc(CC(N)=O)c(C#N)c1-c1cc(Cl)c(O)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe683d00dcf449668d67301cdeeb9755 | CN1CCN(S(=O)(=O)c2ccc(-c3c(C#N)c(N)nc(S)c3C#N)cc2)CC1.NC(=O)CBr>>CN1CCN(S(=O)(=O)c2ccc(-c3c(C#N)c(N)nc(SCC(N)=O)c3C#N)cc2)CC1 | C[NH+]1CCOCC1.NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)S(=O)(=O)N1CCN(CC1)C)C#N)S.BrCC(=O)N.C(=O)(O)[O-].[Na+]>>NC1=C(C(=C(C(=N1)SCC(=O)N)C#N)C1=CC=C(C=C1)S(=O)(=O)N1CCN(CC1)C)C#N | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][c:12](-[c:13]3[c:14]([C:15]#[N:16])[c:17]([NH2:18])[n:19][c:20]([SH:21])[c:26]3[C:27]#[N:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1.Br[CH2:22][C:23]([NH2:24])=[O:25]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][c:12](-[... | CN1CCN(S(=O)(=O)c2ccc(-c3c(C#N)c(N)nc(S)c3C#N)cc2)CC1.NC(=O)CBr | CN1CCN(S(=O)(=O)c2ccc(-c3c(C#N)c(N)nc(SCC(N)=O)c3C#N)cc2)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=S(=O)(c1ccc(-c2ccncc2)cc1)N1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[SH;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[N;D1;H2:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | 84 mg (0.163 mmol) of 2-amino-4-{4-[(4-methylpiperazino)sulfonyl]phenyl}-6-sulfanyl-3,5-pyridinedicarbonitrile N-methylmorpholinium salt together with 53.3 mg (0.244 mmol) of bromoacetamide and 54.7 mg (0.65 mmol) of NaHCO3 are stirred in 0.5 ml of DMF overnight. After filtration, the reaction solution is initially pur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccncc1 | HBr | CN(C)C=O | null | null | CN1CCN(S(=O)(=O)c2ccc(-c3c(C#N)c(N)nc(S)c3C#N)cc2)CC1.NC(=O)CBr>CN(C)C=O>CN1CCN(S(=O)(=O)c2ccc(-c3c(C#N)c(N)nc(SCC(N)=O)c3C#N)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-724d98e1f7214e958705c4e6bea3c13b | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(OCC(=O)[O-])cc1.NC(=O)CBr>>N#Cc1c(N)nc(SCC(N)=O)c(C#N)c1-c1ccc(OCC(=O)O)cc1 | C[NH+]1CCOCC1.NC1=NC(=C(C(=C1C#N)C1=CC=C(OCC(=O)[O-])C=C1)C#N)S.BrCC(=O)N.C(=O)(O)[O-].[Na+]>>NC1=NC(=C(C(=C1C#N)C1=CC=C(OCC(=O)O)C=C1)C#N)SCC(=O)N | [N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([SH:8])[c:13]([C:14]#[N:15])[c:16]1-[c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][C:23](=[O:24])[O-:25])[cH:26][cH:27]1.Br[CH2:9][C:10]([NH2:11])=[O:12]>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][C:10]([NH2:11])=[O:12])[c:13]([C:14]#[N:15])[c:16]1-[c:17]1[cH:18][cH:19... | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(OCC(=O)[O-])cc1.NC(=O)CBr | N#Cc1c(N)nc(SCC(N)=O)c(C#N)c1-c1ccc(OCC(=O)O)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 85d2acf70285ed50a6b1d7dac5c36c10c2ab2c6642a5fdba82c5bea3ff5f3826 | 3fc96152889a4180490b6d2eb2ae57fb3cc9f90d4d42317e75605418ce19aa61 | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8].[SH;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[C:5]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7].[N;D1;H2:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13] | null | [] | null | null | null | null | 135 mg (0.316 mmol) of 2-[4-(2-amino-3,5-dicyano-6-sulfanyl-4-pyridinyl)-phenoxy]acetic acid N-methylmorpholinium salt together with 103.3 mg (0.474 mmol) of bromoacetamide and 106.1 mg (1.263 mmol) of NaHCO3 are stirred in 0.5 ml of DMF overnight. After filtration, the reaction solution is prepurified by preparative H... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Carboxylic acid.Monosulfide | null | null | c1ccncc1.c1ccccc1 | Br- | CN(C)C=O | null | null | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(OCC(=O)[O-])cc1.NC(=O)CBr>CN(C)C=O>N#Cc1c(N)nc(SCC(N)=O)c(C#N)c1-c1ccc(OCC(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e36129c4df9e41db88ae8119b73049f1 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(C(=O)[O-])cc1.NC(=O)CBr>>N#Cc1c(N)nc(SCC(N)=O)c(C#N)c1-c1ccc(C(=O)O)cc1 | C[NH+]1CCOCC1.NC1=NC(=C(C(=C1C#N)C1=CC=C(C(=O)[O-])C=C1)C#N)S.BrCC(=O)N.C(=O)(O)[O-].[Na+]>>NC1=NC(=C(C(=C1C#N)C1=CC=C(C(=O)O)C=C1)C#N)SCC(=O)N | [N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([SH:8])[c:13]([C:14]#[N:15])[c:16]1-[c:17]1[cH:18][cH:19][c:20]([C:21](=[O:22])[O-:23])[cH:24][cH:25]1.Br[CH2:9][C:10]([NH2:11])=[O:12]>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][C:10]([NH2:11])=[O:12])[c:13]([C:14]#[N:15])[c:16]1-[c:17]1[cH:18][cH:19][c:20]([C:21]... | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(C(=O)[O-])cc1.NC(=O)CBr | N#Cc1c(N)nc(SCC(N)=O)c(C#N)c1-c1ccc(C(=O)O)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 85d2acf70285ed50a6b1d7dac5c36c10c2ab2c6642a5fdba82c5bea3ff5f3826 | 3fc96152889a4180490b6d2eb2ae57fb3cc9f90d4d42317e75605418ce19aa61 | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[O-;H0;D1:5]-[C:6](=[O;D1;H0:7])-[c:8].[SH;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[N;D1;H2:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | null | [] | null | null | null | null | 72 mg (0.18 mmol) of 2-[4-(2-amino-3,5-dicyano-6-sulfanyl-4-pyridinyl)benzoic acid N-methylmorpholinium salt together with 59.2 mg (0.27 mmol) of bromoacetamide and 60.9 mg (0.72 mmol) of NaHCO3 are stirred in 0.5 ml of DMF overnight. After filtration, the reaction solution is prepurified by preparative HPLC. The isola... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Carboxylic acid.Monosulfide | null | null | c1ccncc1.c1ccccc1 | Br- | CN(C)C=O | null | null | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(C(=O)[O-])cc1.NC(=O)CBr>CN(C)C=O>N#Cc1c(N)nc(SCC(N)=O)c(C#N)c1-c1ccc(C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a62b3572d6d4f85bafef42a02ec4483 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1.OCCBr>>N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc(O)cc1 | BrCCO.C([O-])(O)=O.[Na+].NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)S>>NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)O)C#N)SCCO | [N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([SH:8])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]1.Br[CH2:9][CH2:10][OH:11]>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][CH2:10][OH:11])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]1 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1.OCCBr | N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc(O)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | 8 | HOUR | 26.8 mg (0.1 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile are dissolved in 0.2 ml of dimethylformamide. 20 mg (0.238 mmol) of solid sodium bicarbonate are added, followed by a solution of 18.74 mg (0.15 mmol) of 2-bromoethanol in 0.06 ml of dimethylformamide. The reaction mixture is shaken... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccccc1 | HBr | CN(C=O)C | null | 8 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc(O)cc1.OCCBr>CN(C=O)C>N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc(O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f87e5dfbcd364d2c8293d075f4d09f50 | CC(=O)Nc1ccc(C=O)cc1.N#CCC#N>>CC(=O)Nc1ccc(C=C(C#N)C#N)cc1 | N(C(=O)C)C1=CC=C(C=O)C=C1.C(CC#N)#N>>C(#N)C(=CC1=CC=C(C=C1)NC(C)=O)C#N | O=[CH:9][c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:16][cH:15]1.[CH2:10]([C:11]#[N:12])[C:13]#[N:14]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[C:10]([C:11]#[N:12])[C:13]#[N:14])[cH:15][cH:16]1 | CC(=O)Nc1ccc(C=O)cc1.N#CCC#N | CC(=O)Nc1ccc(C=C(C#N)C#N)cc1 | null | N1CCCCC1 | C(C)O | C-C Coupling | Knoevenagel Condensation | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9]>>[N;D1;H0:5]#[C:6]-[C;H0;D3;+0:7](-[C:8]#[N;D1;H0:9])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 32.6 g (0.2 mol) of 4-acetaminobenzaldehyde and 13.74 g (0.208 mol) of malononitrile are initially charged in 140 ml of ethanol, and 24 drops of piperidine are added. The mixture is stirred at reflux for 30 min. After cooling, the crystals are filtered off with suction and dried.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1 | HO- | N1CCCCC1.C(C)O | null | null | CC(=O)Nc1ccc(C=O)cc1.N#CCC#N>N1CCCCC1.C(C)O>CC(=O)Nc1ccc(C=C(C#N)C#N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c08b117f2676448eb81e4c74ab745903 | CC(=O)Nc1ccc(C=C(C#N)C#N)cc1.N#CCC#N.Sc1ccccc1>>CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(Sc3ccccc3)c2C#N)cc1 | C(C)N(CC)CC.C(#N)C(=CC1=CC=C(C=C1)NC(C)=O)C#N.C(CC#N)#N.C1(=CC=CC=C1)S>>NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)NC(C)=O)C#N)SC1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[C:24]([C:16]#[N:15])[C:25]#[N:26])[cH:27][cH:28]1.[CH2:10]([C:11]#[N:12])[C:13]#[N:14].[SH:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]#[N:12])[c:13]([NH2:14])[n:15][c:16]([S:17][c:18]3[cH... | CC(=O)Nc1ccc(C=C(C#N)C#N)cc1.N#CCC#N.Sc1ccccc1 | CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(Sc3ccccc3)c2C#N)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 406aa28238d3ea734bb169ab27ec17c6ea5414d0a85bd625dba80f3c83d14725 | 9a8a9e21625984e496f3a9e0ab4c71bb6dfc3b788aaebe22d08d8a732c4c178c | c1ccc(Sc2cc(-c3ccccc3)ccn2)cc1 | [N;D1;H0:1]#[C:2]-[C;H0;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])=[CH;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[N;D1;H0:12]#[C:13]-[CH2;D2;+0:14]-[C;H0;D2;+0:15]#[N;H0;D1;+0:16].[SH;D1;+0:17]-[c:18](:[c:19]):[c:20]>>[N;D1;H0:12]#[C:13]-[c;H0;D3;+0:14]1:[c;H0;D3;+0:15](-[NH2;D1;+0:16]):[n;H0;D2;+0:5]:[c;H0;D3;... | null | [] | null | null | null | null | 19 g (0.09 mol) of N-[4-(2,2-dicyanovinyl)phenyl]acetamide, 5.95 g (0.09 mol) of malononitrile and 9.91 g (0.09 mol) of thiophenol are initially charged in 120 ml of ethanol, and 0.4 ml of triethylamine are added. The mixture is stirred at reflux for 2 h, during which the product crystallizes. After cooling, the produc... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile.Aromatic thiol | Primary amine.Monosulfide | null | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | null | C(C)O | null | null | CC(=O)Nc1ccc(C=C(C#N)C#N)cc1.N#CCC#N.Sc1ccccc1>C(C)O>CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(Sc3ccccc3)c2C#N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5ff107b1d0b4f2fa5f7f78f1c0c66f3 | CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(Sc3ccccc3)c2C#N)cc1>>CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(S)c2C#N)cc1 | NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)NC(C)=O)C#N)SC1=CC=CC=C1.[S-2].[Na+].[Na+].Cl>>NC1=NC(=C(C(=C1C#N)C1=CC=C(C=C1)NC(C)=O)C#N)S | c1ccc([S:17][c:16]2[n:15][c:13]([NH2:14])[c:10]([C:11]#[N:12])[c:9](-[c:8]3[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:22][cH:21]3)[c:18]2[C:19]#[N:20])cc1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]#[N:12])[c:13]([NH2:14])[n:15][c:16]([SH:17])[c:18]2[C:19]#[N:20])[cH:21][cH:22]1 | CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(Sc3ccccc3)c2C#N)cc1 | CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(S)c2C#N)cc1 | null | null | CN(C)C=O | Deprotection | OtherReaction | 785611756aff29aa55293576841f24f47e0b8aca6084ff58df84df5db1ede00b | 30464763b1f3b86eec15b9cd012229de4a24ef37ee861ad1e806c0a745137bee | c1ccc(-c2ccncc2)cc1 | [c:1]:[#7;a:2]:[c:3](-[S;H0;D2;+0:4]-c1:c:c:c:c:c:1):[c:5]>>[SH;D1;+0:4]-[c:3](:[c:5]):[#7;a:2]:[c:1] | null | [] | 80 | CELSIUS | 2 | HOUR | Under argon, 1.16 g (3 mmol) of N-{4-[2-amino-3,5-dicyano-6-(phenylsulfanyl)-4-pyridinyl]phenyl}-acetamide are dissolved in 10 ml of DMF, 0.78 g (10 mmol) of sodium sulfide are added and the mixture is stirred at 80° C. for 2 h. 20 ml of 1N HCl are then added and the resulting crystals are filtered off with suction and... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Aromatic thiol | c1ccccc1 | null | c1ccccc1.c1ccncc1 | Other | CN(C)C=O | 80 | 2 | CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(Sc3ccccc3)c2C#N)cc1>CN(C)C=O>CC(=O)Nc1ccc(-c2c(C#N)c(N)nc(S)c2C#N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86a83da1fa074becaad5021827bd0a08 | CC(NC(=O)c1cc(C(=O)O)cc(N(C)S(C)(=O)=O)c1)c1ccccc1.CCN(C(C)C)C(C)C.CN(C)C=O.On1nnc2ccccc21>>COc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)c2cc(C(=O)NC(C)c3ccccc3)cc(N(C)S(C)(=O)=O)c2)c1 | CN(S(=O)(=O)C)C=1C=C(C(=O)O)C=C(C1)C(NC(C)C1=CC=CC=C1)=O.O.ON1N=NC2=C1C=CC=C2.C(C)(C)N(CC)C(C)C.CN(C)C=O>>OC(C(CC1=CC=CC=C1)NC(C1=CC(C(=O)NC(C)C2=CC=CC=C2)=CC(=C1)N(S(=O)(=O)C)C)=O)CNCC1=CC(=CC=C1)OC | O[C:27]([c:26]1[cH:25][c:24]([C:22](=[O:23])[NH:29][CH:30]([CH3:31])[c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[cH:46][c:39]([N:40]([CH3:41])[S:42]([CH3:43])(=[O:44])=[O:45])[cH:38]1)=[O:28].[CH3:3][CH:47]([N:9]([CH2:8][CH3:7])[CH:10]([CH3:4])[CH3:6])[CH3:14].N([CH3:1])([CH:11]=[O:12])[CH3:13].n1[c:15]2[cH:16][cH:17][... | CC(NC(=O)c1cc(C(=O)O)cc(N(C)S(C)(=O)=O)c1)c1ccccc1.CCN(C(C)C)C(C)C.CN(C)C=O.On1nnc2ccccc21 | COc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)c2cc(C(=O)NC(C)c3ccccc3)cc(N(C)S(C)(=O)=O)c2)c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 28cd06eb8619ec6e32756a20d87de0681943a75556141b4e61125f2dbc5040bb | c9f738fd1672edfbdbf29c91727d6d4f410007f757bdd651961c550b5e7e4eee | O=C(NCc1ccccc1)c1cccc(C(=O)NC(CCNCc2ccccc2)Cc2ccccc2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10](-[C;D1;H3:11])-[c:12]):[c:13].[CH3;D1;+0:14]-N(-[CH3;D1;+0:15])-[CH;D2;+0:16]=[O;H0;D1;+0:17].[CH3;D1;+0:18]-[CH;D3;+0:19](-[CH3;D1;+0:20])-[N;H0;D3;+0:21](-[C:22]-[CH3;D1;+0:23])-[CH;D3;+0:24](-[CH3;D1;+0:25])-[C... | null | [] | null | null | null | null | Tert-butyl 3-hydroxy-4-(3-methoxybenzylamino)-1-phenylbutan-2-ylcarbamate was obtained in a single step by the ring opening reaction of tert-butyl-(1-oxiranyl-2-phenylethyl)-carbamate with 3-methoxybenzylamine under reflux condition in 2-propanol. Deprotection of Boc group by treatment of TFA in CH2Cl2 or methanolic HC... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Tertiary amide.Tertiary amine | Ether.Secondary amide.Secondary amide.Secondary alcohol.Secondary amine | c1ccc2[nH]nnc2c1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CC(NC(=O)c1cc(C(=O)O)cc(N(C)S(C)(=O)=O)c1)c1ccccc1.CCN(C(C)C)C(C)C.CN(C)C=O.On1nnc2ccccc21>C(Cl)Cl>COc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)c2cc(C(=O)NC(C)c3ccccc3)cc(N(C)S(C)(=O)=O)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ca783e74b7f4afda7fdf29c9133cd08 | CNCc1ccccc1.COC(=O)c1cc(C(=O)OC)cc(N(C)S(C)(=O)=O)c1>>COC(=O)c1cc(C(=O)NC(C)c2ccccc2)cc(N(C)S(C)(=O)=O)c1 | CN(S(=O)(=O)C)C=1C=C(C=C(C(=O)OC)C1)C(=O)OC.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.CCN(C(C)C)C(C)C.CNCC1=CC=CC=C1>>CN(S(=O)(=O)C)C=1C=C(C(=O)OC)C=C(C1)C(NC(C)C1=CC=CC=C1)=O | [NH:10]([CH2:11][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH3:12].CO[C:8]([c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:27][c:20]([N:21]([CH3:22])[S:23]([CH3:24])(=[O:25])=[O:26])[cH:19]1)=[O:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8](=[O:9])[NH:10][CH:11]([CH3:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:... | CNCc1ccccc1.COC(=O)c1cc(C(=O)OC)cc(N(C)S(C)(=O)=O)c1 | COC(=O)c1cc(C(=O)NC(C)c2ccccc2)cc(N(C)S(C)(=O)=O)c1 | null | null | null | Acylation | OtherReaction | 808dc150d36d738dfb344b16687a23eb64ff56ba5e7b9811a61bcf2a629ab9d4 | f18ab3ec7f8f7b68cd60322853620cf948305392319293d368e811e4b4883da3 | O=C(NCc1ccccc1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[NH;D2;+0:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[CH3;D1;+0:6]-[CH;D3;+0:8](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | Dimethyl 5-aminoisophthalate was mesylated by treating with methane sulfonylchloride and pyridine in dichloromethane. Then N-alkylation with methyl iodide under NaH/DMF condition gave dimethyl 5-(N-methylmethylsulfonamnido)isophthalate. Selective hydrolysis of dimethyl 5-(N-methylmethylsulfonamido)isophthalate, followe... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CNCc1ccccc1.COC(=O)c1cc(C(=O)OC)cc(N(C)S(C)(=O)=O)c1>>COC(=O)c1cc(C(=O)NC(C)c2ccccc2)cc(N(C)S(C)(=O)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9b67d4b36004ece928ef24a89ab9278 | CC(C)(C)OC(=O)NC(Cc1ccccc1)C1CO1.COc1cccc(CN)c1>>COc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)OC(C)(C)C)c1 | C(C)(C)(C)OC(NC(CC1=CC=CC=C1)C1OC1)=O.COC=1C=C(CN)C=CC1>>COC=1C=C(CNCC(C(CC2=CC=CC=C2)NC(OC(C)(C)C)=O)O)C=CC1 | [CH2:10]1[CH:11]([CH:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[O:12]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][CH:11]([OH:12])[CH:13]([CH2:14][c:15]2[cH... | CC(C)(C)OC(=O)NC(Cc1ccccc1)C1CO1.COc1cccc(CN)c1 | COc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)OC(C)(C)C)c1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(CCCCNCc2ccccc2)cc1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[NH;D2;+0:5]-[C:6]-[c:7] | 77 | [{"value": 77.0, "product": "COC=1C=C(CNCC(C(CC2=CC=CC=C2)NC(OC(C)(C)C)=O)O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of tert-butyl-(1-oxiranyl-2-phenylethyl)-carbamate (131.6 mg, 0.5 mmol), 3-methoxy-benzylamine (0.25 mL, 2 mmol) in 3 mL of 2-propanol was heated to reflux for 12 h to afford tert-butyl 4-(3-methoxybenzylamino)-3-hydroxy-1-phenylbutan-2-ylcarba-mate. The solvent was evaporated and the crude produc... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.c1ccccc1 | null | CC(C)O | null | null | CC(C)(C)OC(=O)NC(Cc1ccccc1)C1CO1.COc1cccc(CN)c1>CC(C)O>COc1cccc(CNCC(O)C(Cc2ccccc2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14cd69973a56476394dd9346dd853cfe | CC(=O)c1cccnc1.[NH4+]>>CC(N)c1cccnc1 | Cl.C(#N)[BH3-].[Na+].C(C)(=O)C=1C=NC=CC1.C(C)(=O)[O-].[NH4+]>>N1=CC(=CC=C1)C(C)N | O=[C:2]([CH3:1])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1.[NH4+:3]>>[CH3:1][CH:2]([NH2:3])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | CC(=O)c1cccnc1.[NH4+] | CC(N)c1cccnc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccncc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[NH4+;D0:8]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH2;D1;+0:8])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | 20 | MINUTE | To a solution of 3-acetylpridine (82.6 mmol) in methanol (200 mL) was added ammonium acetate (1.03 mol) in one portion at room temperature. After the mixture has been stirred for 20 min, sodium cyanoborohydride (57.8 mmol) was added to this mixture. After being stirring for one day, 6 M hydrochloric acid was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | c1ccncc1 | HO- | CO | null | 0.333333 | CC(=O)c1cccnc1.[NH4+]>CO>CC(N)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbc5cb693c1a4ee4ad60661f5959feb5 | C=O.CC(C)(C)OC(=O)NCc1cccc(N)c1>>CNc1cccc(CNC(=O)OC(C)(C)C)c1 | NC=1C=C(CNC(OC(C)(C)C)=O)C=CC1.C=O.C(#N)[BH3-].[Na+]>>CNC=1C=C(CNC(OC(C)(C)C)=O)C=CC1 | O=[CH2:1].[NH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17]1>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17]1 | C=O.CC(C)(C)OC(=O)NCc1cccc(N)c1 | CNc1cccc(CNC(=O)OC(C)(C)C)c1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive methylation of primary amine with formaldehyde | 51d235def9103cd7a524cbedb590276839772d481304df37a121e64cb81721f4 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccccc1 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Tert-butyl 3-aminobenzylcarbamate was converted to the target molecule following standard reductive amination conditions using formaldehyde and sodium cyanoborohydride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | null | null | null | C=O.CC(C)(C)OC(=O)NCc1cccc(N)c1>>CNc1cccc(CNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b698925d96c4693929fae997b8485d2 | OCc1cncc(OCc2ccccc2)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>[N-]=[N+]=NCc1cncc(OCc2ccccc2)c1 | N12CCCCCC2=NCCC1.C1CCC2=NCCCN2CC1.C(C1=CC=CC=C1)OC=1C=C(C=NC1)CO.C=1C=CC(=CC1)P(=O)(C=2C=CC=CC2)N=[N+]=[N-]>>N(=[N+]=[N-])CC=1C=NC=C(C1)OCC1=CC=CC=C1 | O[CH2:4][c:5]1[cH:6][n:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1.O=P(c1ccccc1)(c1ccccc1)[N:3]=[N+:2]=[N-:1]>>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][n:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | OCc1cncc(OCc2ccccc2)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | [N-]=[N+]=NCc1cncc(OCc2ccccc2)c1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | cfa52427fe008248ccb3b060cca934c64c46f29eb11684ddb953f16825bf2f0e | da5ad8c0affa2dc7232b479927687ff59fae3f37df63d467193897a964229798 | c1ccc(COc2cccnc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].O=P(-[N;H0;D2;+0:7]=[#7;+:8]=[N;-;D1;H0:9])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[N;-;D1;H0:9]=[#7;+:8]=[N;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 65 | [{"value": 65.0, "product": "N(=[N+]=[N-])CC=1C=NC=C(C1)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.4, "product": "N(=[N+]=[N-])CC=1C=NC=C(C1)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | HOUR | To a stirring solution of 250 mg (1.17 mmol) of (5-(benzyloxy)pyridin-3-yl)methanol in 8 mL of toluene was added 310 μL (1.44 mmol) of DPPA. The mixture was cooled to 0° C. and 210 μL (1.44 mmol) of 1,8-diazabicyclo[5.4.0]-undec-7-ene] (DBU) was added. The ice bath was removed, and stirring was continued with wanning t... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Primary alcohol | Azide | c1ccccc1.c1ccccc1 | null | c1ccncc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 0 | 20 | OCc1cncc(OCc2ccccc2)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>[N-]=[N+]=NCc1cncc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b98888c3d3f04ebfb0309fc29f53b5c3 | [N-]=[N+]=NCc1cncc(OCc2ccccc2)c1>>NCc1cncc(OCc2ccccc2)c1 | N(=[N+]=[N-])CC=1C=NC=C(C1)OCC1=CC=CC=C1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C1=CC=CC=C1)OC=1C=C(C=NC1)CN | [N-]=[N+]=[N:1][CH2:2][c:3]1[cH:4][n: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>>[NH2:1][CH2:2][c:3]1[cH:4][n: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 | [N-]=[N+]=NCc1cncc(OCc2ccccc2)c1 | NCc1cncc(OCc2ccccc2)c1 | null | null | C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(COc2cccnc2)cc1 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[N;H0;D2;+0:5]=[N+]=[N-]>>[#7;a:1]:[c:2]:[c:3]-[C:4]-[NH2;D1;+0:5] | null | [] | null | null | null | null | To a stirring solution of 181 mg of 3-(azidomethyl)-5-(benzyloxy)pyridine in 6 mL of THF at 0° C. was added 80.6 mg (2.12 mmol) of LiAlH4. The ice bath was removed and stirring was continued with warming to r.t. After 30 min. the reaction was quenched by adding successively 160 μL of H2O, 160 μL of 15% aqueous NaOH, an... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | C1CCOC1 | null | null | [N-]=[N+]=NCc1cncc(OCc2ccccc2)c1>C1CCOC1>NCc1cncc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aaa8a5b1564243ed80020bd6935f426d | O=C(O)c1cc(F)cc(C(=O)O)c1>>O=C(O)c1ccc(F)c(C(=O)O)c1 | FC1=C(C(=O)O)C=C(C=C1)C.FC=1C=C(C=C(C(=O)O)C1)C(=O)O>>FC1=C(C=C(C(=O)O)C=C1)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:8])[cH:7][c:9]([C:10](=[O:11])[OH:12])[cH:13]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([C:10](=[O:11])[OH:12])[cH:13]1 | O=C(O)c1cc(F)cc(C(=O)O)c1 | O=C(O)c1ccc(F)c(C(=O)O)c1 | null | null | null | Miscellaneous | OtherReaction | 8b388a01d4ace5c68f33e893b8a373b9c9e85f67fc49eb8a1980866a8512628a | 50b3263108b11afcbe25d1a908d5d62fc9b7a01756ee297f5e635ade1a0cdefb | c1ccccc1 | [F;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8]:[c:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[cH;D2;+0:13]:1>>[F;H0;D1;+0:1]-[c;H0;D3;+0:13]1:[cH;D2;+0:2]:[c:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8]:[c:9]:1-[C:10](=[O;D1;H0:11])-[O;D1;H1:12] | null | [] | null | null | null | null | The precursor compound was synthesized from 2-fluoro-5-methylbenzoic acid following the procedure described for 5-fluoro-isophthalic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | null | null | null | O=C(O)c1cc(F)cc(C(=O)O)c1>>O=C(O)c1ccc(F)c(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4fbd592b11fb4b46a27e7dc82418659a | Cc1ccc(C)c(C(=O)O)c1.O=C(O)c1cc(F)cc(C(=O)O)c1>>Cc1ccc(C(=O)O)cc1C(=O)O | CC1=C(C(=O)O)C=C(C=C1)C.FC=1C=C(C=C(C(=O)O)C1)C(=O)O>>CC1=C(C=C(C(=O)O)C=C1)C(=O)O | C[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:10]([C:11](=[O:12])[OH:13])[cH:9]1.O=C(O)c1cc(F)cc([C:6](=[O:7])[OH:8])c1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[C:11](=[O:12])[OH:13] | Cc1ccc(C)c(C(=O)O)c1.O=C(O)c1cc(F)cc(C(=O)O)c1 | Cc1ccc(C(=O)O)cc1C(=O)O | null | null | null | C-C Coupling | OtherReaction | 5c84aad0ec599bb43e5c7982d1979371ca7d18948e79cb850a0bbae890f65f45 | a65e76a3bc21fa573e10bcfac3bc48313eb97ae43062b329739ae1d877e0bcec | c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].F-c1:c:c(-C(-O)=O):c:c(-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;D1;H1:11]):c:1>>[O;D1;H0:7]=[C:6](-[O;D1;H1:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;D1;H1:11]):[c:2]:[c:3] | null | [] | null | null | null | null | The precursor compound was synthesized from 2,5-dimethylbenzoic acid following the procedure described for 5-fluoro-isophthalic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | null | null | null | Cc1ccc(C)c(C(=O)O)c1.O=C(O)c1cc(F)cc(C(=O)O)c1>>Cc1ccc(C(=O)O)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8fda7e41797e40d284ad385eb199a360 | CC(=O)CCl.C[C@H](NC(=O)OC(C)(C)C)C(N)=S>>Cc1csc(C(C)NC(=O)OC(C)(C)C)n1 | C(=O)(OC(C)(C)C)N[C@@H](C)C(N)=S.ClCC(C)=O.C([O-])([O-])=O.[Ca+2]>>CC=1N=C(SC1)C(C)NC(OC(C)(C)C)=O | O=[C:2]([CH3:1])[CH2:3]Cl.[S:4]=[C:5]([C@H:6]([CH3:7])[NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[NH2:16]>>[CH3:1][c:2]1[cH:3][s:4][c:5]([CH:6]([CH3:7])[NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16]1 | CC(=O)CCl.C[C@H](NC(=O)OC(C)(C)C)C(N)=S | Cc1csc(C(C)NC(=O)OC(C)(C)C)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1cscn1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C;D1;H3:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[C@@H;D3;+0:12](-[C;D1;H3:13])-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[S;H0;D1;+0:16]>>[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[CH;D3;+0:12](-[C;D1;H3:13]... | 48 | [{"value": 48.0, "product": "CC=1N=C(SC1)C(C)NC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of BOC-alanine-thioamide (1.39 g, 6.81 mmoles), chloroacetone (0.65 mL, 8.18 mmoles) and calcium carbonate (1.0 g, 10.22 mmoles) were refluxed in ethanol (25 mL) for 4 h. The reaction was cooled to room temperature and quenched with 2OmL of saturated aq. NaHCO3 solution. Ethanol was evaporated under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1 | HCl | C(C)O | null | null | CC(=O)CCl.C[C@H](NC(=O)OC(C)(C)C)C(N)=S>C(C)O>Cc1csc(C(C)NC(=O)OC(C)(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-849eb0be731b49e3a6ea4f7a033fdcef | NCC1CCN(C(=O)OCc2ccccc2)CC1.O=BC=NC(Cc1ccccc1)C1CO1>>O=BC=NC(Cc1ccccc1)C(O)CNCC1CCN(C(=O)OCc2ccccc2)CC1 | O1C(C1)C(CC1=CC=CC=C1)N=CB=O.NCC1CCN(CC1)C(=O)OCC1=CC=CC=C1>>OC(CNCC1CCN(CC1)C(=O)OCC1=CC=CC=C1)C(CC1=CC=CC=C1)N=CB=O | [NH2:16][CH2:17][CH:18]1[CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:32][CH2:33]1.[O:1]=[B:2][CH:3]=[N:4][CH:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]1[O:14][CH2:15]1>>[O:1]=[B:2][CH:3]=[N:4][CH:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[... | NCC1CCN(C(=O)OCc2ccccc2)CC1.O=BC=NC(Cc1ccccc1)C1CO1 | O=BC=NC(Cc1ccccc1)C(O)CNCC1CCN(C(=O)OCc2ccccc2)CC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | O=C(OCc1ccccc1)N1CCC(CNCCCCc2ccccc2)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[CH2;D2;+0:6]-[C:5](-[C:4])-[OH;D1;+0:7] | 121.6 | [{"value": 121.6, "product": "OC(CNCC1CCN(CC1)C(=O)OCC1=CC=CC=C1)C(CC1=CC=CC=C1)N=CB=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(oxiran-2-yl)-N-((oxoboryl)methylene)-2-phenylethanamine (1.61 mmol, 424 mg) and benzyl 4-(aminomethyl)piperidine-1-carboxylate (1.94 nmnol, 480 mg) in isopropanol (20 mL) was heated at 80° C. for overnight. Evaporated the solvent and purified by flash chromatography to get benzyl 4-((2-hydroxy-3-((oxoboryl)methylene... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | C(C)(C)O | null | null | NCC1CCN(C(=O)OCc2ccccc2)CC1.O=BC=NC(Cc1ccccc1)C1CO1>C(C)(C)O>O=BC=NC(Cc1ccccc1)C(O)CNCC1CCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-470f26b5a4894efe91e8c20c998849a6 | COC(=O)c1cccc(C(=O)[O-])c1.Cc1csc(CNC(C)C)n1>>COC(=O)c1cccc(C(=O)N(Cc2nc(C)cs2)C(C)C)c1 | CC=1N=C(SC1)CNC(C)C.C(C1=CC(C(=O)[O-])=CC=C1)(=O)OC>>C(C)(C)N(C(=O)C=1C=C(C(=O)OC)C=CC1)CC=1SC=C(N1)C | [O-][C:10]([c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:23]1)=[O:11].[NH:12]([CH2:13][c:14]1[n:15][c:16]([CH3:17])[cH:18][s:19]1)[CH:20]([CH3:21])[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][c:14]2[n:15][c:16]([CH3:17])[cH:18][s:19]2)[CH:20]([CH3:21])[CH... | COC(=O)c1cccc(C(=O)[O-])c1.Cc1csc(CNC(C)C)n1 | COC(=O)c1cccc(C(=O)N(Cc2nc(C)cs2)C(C)C)c1 | null | CCN(CC)CC | O=S(Cl)Cl.C(Cl)Cl | Acylation | OtherReaction | 4cfceec1aea84a79816c41fae0c81172c18248078f31ae4437446c5821f56e86 | abe2f9e72dd5fcaae131e2f313c58ce84793c9db4899e2929efc0f663f613b41 | O=C(NCc1nccs1)c1ccccc1 | [#16;a:1]:[c:2](-[C:3]-[NH;D2;+0:4]-[C:5](-[C;D1;H3:6])-[C;D1;H3:7]):[#7;a:8].[O-]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]>>[#16;a:1]:[c:2](-[C:3]-[N;H0;D3;+0:4](-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]):[#7;a:8] | 93 | [{"value": 93.0, "product": "C(C)(C)N(C(=O)C=1C=C(C(=O)OC)C=CC1)CC=1SC=C(N1)C", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 30 | MINUTE | Et3N (1 drop, catalytic) was added to a stirred suspension of mono-Methyl isophthalate (0.294 mmol, 1.0 eq) in 2 ml SOCl2 under Ar. The mixture was heated to reflux at 90° C. for 2 h. The reaction was cooled to RT, and the solvent was removed in vacuo. The residue was placed under an Ar atmosphere and dissolved in 2 ml... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amide | null | null | c1ccccc1.c1cscn1 | HO- | CCN(CC)CC.O=S(Cl)Cl.C(Cl)Cl | 90 | 0.5 | COC(=O)c1cccc(C(=O)[O-])c1.Cc1csc(CNC(C)C)n1>CCN(CC)CC.O=S(Cl)Cl.C(Cl)Cl>COC(=O)c1cccc(C(=O)N(Cc2nc(C)cs2)C(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b687ac30e4d84a9bac08ed01851f123f | CC(C)(C)O.Cc1cc(CC(=O)O)on1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>Cc1cc(CNC(=O)OC(C)(C)C)on1 | CC1=NOC(=C1)CC(=O)O.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].C(C)N(CC)CC.C(C)(C)(C)O>>CC1=NOC(=C1)CNC(OC(C)(C)C)=O | [OH:9][C:10]([CH3:11])([CH3:12])[CH3:13].O[C:7]([CH2:5][c:4]1[cH:3][c:2]([CH3:1])[n:15][o:14]1)=[O:8].[N-]=[N+]=[N:6]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[o:14][n:15]1 | CC(C)(C)O.Cc1cc(CC(=O)O)on1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | Cc1cc(CNC(=O)OC(C)(C)C)on1 | null | null | null | Protection | OtherReaction | df61fc599aa8adfb11bba92c1184c87669f8cd7e23eea6248759894a330e0e1a | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | c1cnoc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[c:4]1:[#8;a:5]:[#7;a:6]:[c:7]:[c:8]:1.O=P(-[N;H0;D2;+0:9]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[OH;D1;+0:14]>>[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[O;H0;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-... | 10 | [{"value": 10.0, "product": "CC1=NOC(=C1)CNC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 321 mg (2.27 mmol) of 2-(3-methylisoxazol-5-yl)acetic acid, 0.5 mL (2.32 mmol) of diphenylphosphorylazide (DPPA), and 0.35 mL (2.51 mmol) of triethylamine in 30 mL of distilled tert-butyl alcohol was refluxed for 13.5 hours. The solution was concentrated, and the crude residue was dissolved in EtOAc. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | c1ccccc1.c1ccccc1 | null | c1cnoc1 | HO- | null | null | null | CC(C)(C)O.Cc1cc(CC(=O)O)on1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>Cc1cc(CNC(=O)OC(C)(C)C)on1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef88394f1bbb4e17902870fb7589167d | BrCc1ccccc1.O=C(O)c1cncc(O)c1>>COC(=O)c1cncc(OCc2ccccc2)c1 | OC=1C=NC=C(C(=O)O)C1.C(=O)([O-])[O-].[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC=1C=NC=C(C(=O)OC)C1 | Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[OH:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([OH:10])[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | BrCc1ccccc1.O=C(O)c1cncc(O)c1 | COC(=O)c1cncc(OCc2ccccc2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 61d8f2c0f6f34647c4f3327f794817a40ca51b06bac1ed159c969fa398ffed2b | ce9b0a26b75ecadeee5e59813a60d1276e320d2d60474ed4c9be770045f98229 | c1ccc(COc2cccnc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]1:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]:[#7;a:13]:[c:14]:1>>[C;D1;H3:15]-[O;H0;D2;+0:7]-[C:6](=[O;D1;H0:5])-[c:8]1:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:[#7;a:13]:[c:14]:1 | 28 | [{"value": 28.0, "product": "C(C1=CC=CC=C1)OC=1C=NC=C(C(=O)OC)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.9, "product": "C(C1=CC=CC=C1)OC=1C=NC=C(C(=O)OC)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 818 mg (5.34 mmol) of 5-hydroxynicotinic acid, 1.70 g (12.3 mmol) of K2CO3, and 1.0 mL (8.41 mmol) of benzyl bromide in 25 mL of DMF was heated at 60° C. under Ar for 16 h. The mixture was filtered through cotton, and the residue was dissolved in CHCl3. The organic layer was washed with water (2×30 mL), br... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Aromatic alcohol | Ester.Ether | null | null | c1ccncc1.c1ccccc1 | null | CN(C)C=O | 60 | null | BrCc1ccccc1.O=C(O)c1cncc(O)c1>CN(C)C=O>COC(=O)c1cncc(OCc2ccccc2)c1 |
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