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-0387783899c642a8b7eb4ba379bcdf5d | ord-4d49f2de2fea4e568118fe4805b7b8f7 | COc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>>COc1cc(-c2nc3ccccc3o2)ccc1CC#N | [C-]#N.[Na+].BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.O>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)OC | Br[CH2:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1.[C-:19]#[N:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][C:19]#[N:20] | COc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N | COc1cc(-c2nc3ccccc3o2)ccc1CC#N | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(-c2nc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | A mixture of, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (318 mg, 1 mmol), dimethylformamide (7.5 mL) and deionzed water (2.5 mL) was stirred at rt. Sodium cyanide (150 mg, 3.0 mmol) was added to reaction. After 3 h, dimethylformamide (10 mL) was added to help dissolve solids in reaction mixture. Let reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1.c1ccc2ocnc2c1 | Br- | CN(C=O)C | null | 3 | COc1cc(-c2nc3ccccc3o2)ccc1CBr.[C-]#N>CN(C=O)C>COc1cc(-c2nc3ccccc3o2)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34ed716cd4364862b6fb3902c6311fb6 | BrCCCCBr.COc1cc(-c2nc3ccccc3o2)ccc1CC#N>>COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCCC1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC#N)OC.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].BrCCCCBr>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2(CCCC2)C#N)OC | Br[CH2:21][CH2:22][CH2:23][CH2:24]Br.[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][C:19]#[N:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[C:18]1([C:19]#[N:20])[CH2:21][CH2:22]... | BrCCCCBr.COc1cc(-c2nc3ccccc3o2)ccc1CC#N | COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCCC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 90ff2cdd2efc3b7e3d5fddf28ea72ab16385a91dc99fbace2077f543bebdb44a | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | c1ccc2oc(-c3ccc(C4CCCC4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-Br.[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[N;D1;H0:5]#[C:6]-[C;H0;D4;+0:7]1(-[c:8](:[c:9]):[c:10])-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | null | null | null | null | [4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile (130 mg, 0.49 mmol) in THF (5.0 mL) was cooled to −78° C. under argon atmosphere. Sodium bis(trimethylsilyl)amide (1.8 mL, 1.08 mmol) was added slowly and after fifteen minutes, added 1,4-dibromobutane (0.07 mL, 0.59 mmol) to dark brown reaction mixture. Let mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CCCC1 | c1ccccc1.c1ccc2ocnc2c1.C1CCCC1 | HBr | C1CCOC1 | null | null | BrCCCCBr.COc1cc(-c2nc3ccccc3o2)ccc1CC#N>C1CCOC1>COc1cc(-c2nc3ccccc3o2)ccc1C1(C#N)CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6aab020e505c4013a9621c93cb7e9ea8 | COc1cc(C(=O)O)cc(OC)c1C.Nc1ccccc1O>>COc1ccccc1NC(=O)c1cc(OC)c(C)c(OC)c1 | S(=O)(Cl)Cl.COC=1C=C(C(=O)O)C=C(C1C)OC.NC1=C(C=CC=C1)O.C(C)(C)N(CC)C(C)C>>COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=C(C1C)OC | O[C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([CH3:18])[c:19]([O:20][CH3:21])[cH:22]1.[OH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([CH3:18])[c:19]([O:20][CH3:21])[cH:22]1 | COc1cc(C(=O)O)cc(OC)c1C.Nc1ccccc1O | COc1ccccc1NC(=O)c1cc(OC)c(C)c(OC)c1 | null | null | C1CCOC1 | Acylation | OtherReaction | e490eebb477043dc0542732dd7a6ce49276641802836b4489c620def21f9d46c | fcf68d457905b35c628fee285772653b3fd6812b4e55ecf3f563dfc9713d647a | 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](-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:12]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:7](-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:8] | null | [] | null | null | 8 | HOUR | Thionyl chloride (10 mL) and 3,5-dimethoxy-4-methylbenzoic acid (1.0 g, 5.1 mmol) was refluxed under argon until no starting material was observed by TLC. After cooling reaction mixture to rt, concentrated mixture in vacuo. The resulting brown oil was added to a mixture of 2-aminophenol (580 mg, 5.3 mmol), diisopropyle... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | Ether.Secondary amide | null | null | c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | 8 | COc1cc(C(=O)O)cc(OC)c1C.Nc1ccccc1O>C1CCOC1>COc1ccccc1NC(=O)c1cc(OC)c(C)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-450eaf900c1b41f5a2503bdf4b4d4c54 | COc1ccccc1NC(=O)c1cc(OC)c(C)c(OC)c1>>COc1cc(-c2nc3ccccc3o2)cc(OC)c1C | COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=C(C1C)OC.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>COC=1C=C(C=C(C1C)OC)C=1OC2=C(N1)C=CC=C2 | C[O:14][c:13]1[c:8]([NH:7][C:6](=O)[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:19]([CH3:20])[c:16]([O:17][CH3:18])[cH:15]2)[cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][c:16]([O:17][CH3:18])[c:19]1[CH3:20] | COc1ccccc1NC(=O)c1cc(OC)c(C)c(OC)c1 | COc1cc(-c2nc3ccccc3o2)cc(OC)c1C | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | cca37de9709afcabd4b3174dfe5bb540cf174e2c2293a5aacc2ac5348d22416e | 7a715e0d3d7e660856ee0e7d29a6fc31cd81ad5715093f41ca51d14205e8785e | c1ccc(-c2nc3ccccc3o2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:12]>>[c:3]:[c:2]1:[o;H0;D2;+0:1]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:5]:[c:4]:1:[c:12] | null | [] | null | null | null | null | A mixture of 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide (1.29 g, 4.49 mmol), toluene (22 mL), p-toluenesulfonic acid monohydrate (5.9 g, 31 mmol) and molecular sieves was refluxed until no starting material was observed by TLC. Cooled mixture to rt and filtered, washing with warm chloroform. Removal of solvent... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | null | null | COc1ccccc1NC(=O)c1cc(OC)c(C)c(OC)c1>C1(=CC=CC=C1)C>COc1cc(-c2nc3ccccc3o2)cc(OC)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-394150f62b5b4dda8aa07bbea70ff52f | COc1cc(-c2nc3ccccc3o2)cc(OC)c1C>>c1ccc2ocnc2c1 | COC=1C=C(C=C(C1C)OC)C=1OC2=C(N1)C=CC=C2.C(Cl)(Cl)(Cl)Cl.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.BrN1C(CCC1=O)=O>>O1C=NC2=C1C=CC=C2 | COc1cc(-[c:6]2[o:5][c:4]3[cH:3][cH:2][cH:1][cH:9][c:8]3[n:7]2)cc(OC)c1C>>[cH:1]1[cH:2][cH:3][c:4]2[o:5][cH:6][n:7][c:8]2[cH:9]1 | COc1cc(-c2nc3ccccc3o2)cc(OC)c1C | c1ccc2ocnc2c1 | null | null | CCOC(=O)C | Reduction | OtherReaction | c81702d22f60b39bb722774c6b4018dac51380acf17ac5611d6045cf3fadcc5b | 1556a72485df4201aca96fb7a0c321edf07cb063300030d429a36e916471ff2c | c1ccc2ocnc2c1 | C-O-c1:c:c(-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:2):c:c(-O-C):c:1-C>>[#7;a:2]1:[c:3]:[c:4]:[#8;a:5]:[cH;D2;+0:1]:1 | null | [] | null | null | null | null | A mixture of 2-(3,5-dimethoxy-4-methylphenyl)-1,3-benzoxazole (260 mg, 1 mmol), carbon tetrachloride (4.2 mL), benzoyl peroxide (15 mg, 0.06 mmol) and N-bromosuccinimide (270 mg, 1.5 mmol) was heated to reflux conditions under argon overnight. Concentration of cooled reaction mixture in vacuo afforded a yellow solid. F... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1ccccc1.c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HO- | CCOC(=O)C | null | null | COc1cc(-c2nc3ccccc3o2)cc(OC)c1C>CCOC(=O)C>c1ccc2ocnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ebe673163ca41e2bbd2f1f42373a799 | Cc1ccc(C(=O)O)cc1Cl.O=C1CCC(=O)N1Br>>O=C(O)c1ccc(CBr)c(Cl)c1 | ClC=1C=C(C(=O)O)C=CC1C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrCC1=C(C=C(C(=O)O)C=C1)Cl | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[c:10]([Cl:11])[cH:12]1.O=C1CCC(=O)N1[Br:9]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][Br:9])[c:10]([Cl:11])[cH:12]1 | Cc1ccc(C(=O)O)cc1Cl.O=C1CCC(=O)N1Br | O=C(O)c1ccc(CBr)c(Cl)c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of 3-chloro-4-methylbenzoic acid (5.0 g, 29 mmol), N-bromosuccinimide (5.7 g, 32 mmol), benzoyl peroxide (710 mg, 2.9 mmol) in CCl4 (300 mL) was heated at reflux for 2.5 h. The mixture was concentrated under reduced pressure and dissolved in MTBE. The organic mixture was washed with 1N NaOH (3×25 mL). The aq... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(C(=O)O)cc1Cl.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>O=C(O)c1ccc(CBr)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-768846e0a8dc4bde93680feebe296211 | Cl.O=C(O)c1ccc(CBr)c(Cl)c1.[C-]#N>>N#CCc1ccc(C(=O)Cl)cc1Cl | BrCC1=C(C=C(C(=O)O)C=C1)Cl.[C-]#N.[Na+].Cl>>ClC=1C=C(C(=O)Cl)C=CC1CC#N | [ClH:10].O[C:8]([c:7]1[cH:6][cH:5][c:4]([CH2:3]Br)[c:12]([Cl:13])[cH:11]1)=[O:9].[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[Cl:10])[cH:11][c:12]1[Cl:13] | Cl.O=C(O)c1ccc(CBr)c(Cl)c1.[C-]#N | N#CCc1ccc(C(=O)Cl)cc1Cl | null | null | O.CN(C)C=O | C-C Coupling | OtherReaction | b25a570a619944c75625ecf77d235977d75202b4ed3ff8f5415990749ddac4a9 | e87271a0eba29341fc54289f87ecb789f51fe9203a0af8f3cf795de479e12020 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[C;H0;D3;+0:6](-O)=[O;D1;H0:7]):[c:8]:[c:9]:1.[C-;H0;D1:10]#[N;D1;H0:11].[ClH;D0;+0:12]>>[Cl;H0;D1;+0:12]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:5]1:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[C;H0;D2;+0:10]#[N;D1;H0:11]):[c:9]:[c:8]:1 | null | [] | 80 | CELSIUS | null | null | A suspension of 4-(bromomethyl)-3-chlorobenzoic acid (4.0 g, 16 mmol) in DMF (120 mL) and H2O (40 mL) was treated with NaCN (2.4 g, 49 mmol) and heated to 80° C. for 2 h. The mixture was cooled to rt and acidified with 1N HCl. The aqueous mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were con... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Acyl halide.Nitrile | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 80 | null | Cl.O=C(O)c1ccc(CBr)c(Cl)c1.[C-]#N>O.CN(C)C=O>N#CCc1ccc(C(=O)Cl)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6164288fd3c4bcb8895ec6a0beca9ed | N#CCc1ccc(C(=O)Nc2ncccc2O)cc1Cl>>N#CCc1ccc(-c2nc3ncccc3o2)cc1Cl | ClC=1C=C(C(=O)NC2=NC=CC=C2O)C=CC1CC#N>>ClC1=C(C=CC(=C1)C=1OC=2C(=NC=CC2)N1)CC#N | O=[C:8]([c:7]1[cH:6][cH:5][c:4]([CH2:3][C:2]#[N:1])[c:18]([Cl:19])[cH:17]1)[NH:9][c:10]1[n:11][cH:12][cH:13][cH:14][c:15]1[OH:16]>>[N:1]#[C:2][CH2:3][c:4]1[cH: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][c:18]1[Cl:19] | N#CCc1ccc(C(=O)Nc2ncccc2O)cc1Cl | N#CCc1ccc(-c2nc3ncccc3o2)cc1Cl | null | null | O=P(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 08224b6df024d417030953f413b01e82c02ffa385e73965b18b2fd66be2526fa | e4db370caafce196eb62f60d573e0a03e9af17c2927e176eeb3f4f837c389bef | c1ccc(-c2nc3ncccc3o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[OH;D1;+0:7]):[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[c:5]:[#7;a:4]:[c:3]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[o;H0;D2;+0:7]:[c:6]:1:[c:8] | null | [] | null | null | null | null | 3-chloro-4-(cyanomethyl)-N-(3-hydroxypyridin-2-yl)benzamide (550 mg, 1.9 mmol) was refluxed in POCl3 (15 mL) for 2.5 h. Excess POCl3 was removed by distillation and the mixture was cooled to rt. The crude mixture was diluted with H2O. The aqueous layer was made basic (pH 14) with 1N NaOH and extracted with CH2Cl2 (3×20... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol | null | c1ccncc1 | c1cnc2ncoc2c1 | c1ccccc1.c1cnc2ncoc2c1 | HO- | O=P(Cl)(Cl)Cl | null | null | N#CCc1ccc(C(=O)Nc2ncccc2O)cc1Cl>O=P(Cl)(Cl)Cl>N#CCc1ccc(-c2nc3ncccc3o2)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d309ba83d2484108a07efc99551b2565 | COc1cc(-c2nc3ccccc3o2)ccc1CBr.c1c[nH]nn1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1.COc1cc(-c2nc3ccccc3o2)ccc1Cn1nccn1 | BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1N=NC=C1.C(=O)([O-])[O-].[Cs+].[Cs+]>>COC=1C=C(C=CC1CN1N=NC=C1)C=1OC2=C(N1)C=CC=C2.COC=1C=C(C=CC1CN1N=CC=N1)C=1OC2=C(N1)C=CC=C2 | Br[CH2:41][c:40]1[cH:16][cH:15][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:27][c:26]1[O:25][CH3:24].[nH:19]1[cH:20][cH:21][n:22][n:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][n:19]1[cH:20][cH:21][n:22][n:23]1.[CH... | COc1cc(-c2nc3ccccc3o2)ccc1CBr.c1c[nH]nn1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1.COc1cc(-c2nc3ccccc3o2)ccc1Cn1nccn1 | null | null | CC#N | Aromatic Heterocycle Formation | N-alkylation of secondary amines with alkyl halides | 46112832254b9d7eb76fd770fca4698317982bcde40fd1548b8ff15fc7eb355a | 472eb6d73da5f7026b348a58143222abfbde6aa818697cfe6be183b231c19849 | c1ccc2oc(-c3ccc(Cn4ccnn4)cc3)nc2c1.c1ccc2oc(-c3ccc(Cn4nccn4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4]:[c;H0;D3;+0:5](-[c:6]2:[#7;a:7]:[c:8]:[c:9]:[#8;a:10]:2):[cH;D2;+0:11]:[c:12]:1-[#8:13].[#7;a:14]1:[#7;a:15]:[nH;D2;+0:16]:[c:17]:[c:18]:1>>[#7;a:14]1:[#7;a:15]:[n;H0;D3;+0:16](-[C:19]-[c:20]2:[c:21]:[c:22]:[c;H0;D3;+0:5](-[c:6]3:[#7;a:7]:[c:8]:[c:9]:[#8;a:10]:3):[c:4... | null | [] | null | null | null | null | A slurry of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 1H-1,2,3-triazole (70 mg, 1.0 mmol), and Cs2CO3 (325 mg, 1.0 mmol) and MeCN (10 mL) was stirred vigorously at rt for 8 h. Silica gel (600 mg) was added, and the reaction mixture was concentrated to dryness. The residue was purified b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether | c1ccccc1.c1c[nH]nn1 | c1ccccc1.c1c[nH]nn1.c1ccccc1.c1ccc2ocnc2c1.c1c[nH]nn1 | c1ccccc1.c1ccc2ocnc2c1.c1c[nH]nn1.c1ccccc1.c1ccc2ocnc2c1.c1c[nH]nn1 | Br- | CC#N | null | null | COc1cc(-c2nc3ccccc3o2)ccc1CBr.c1c[nH]nn1>CC#N>COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1.COc1cc(-c2nc3ccccc3o2)ccc1Cn1nccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f615630267445b480096088c21ae399 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cncn1 | COC=1C=C(C=CC1CN1N=NC=C1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1N=CN=C1>>COC=1C=C(C=CC1CN1N=CN=C1)C=1OC2=C(N1)C=CC=C2 | c1n[n:23][n:19]([CH2:18][c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][n:19]1[cH:20][n:21][cH:22][n:23]1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1cncn1 | null | null | null | Miscellaneous | OtherReaction | 426d52038bafec0fcdeaa165a83760516b86a907389f29067055bd95e6ad9ee9 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2oc(-c3ccc(Cn4cncn4)cc3)nc2c1 | [C:1]-[#7;a:2]1:[cH;D2;+0:3]:c:n:[n;H0;D2;+0:4]:1>>[C:1]-[#7;a:2]1:[cH;D2;+0:3]:[#7;a:5]:[c:6]:[n;H0;D2;+0:4]:1 | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 1,2,4-triazole (70 mg, 1.0 mmol) afforded the desired 2-[3-methoxy-4-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-1,3-benzoxazo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]nn1 | c1nc[nH]n1 | c1ccccc1.c1ccc2ocnc2c1.c1nc[nH]n1 | null | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cncn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06bb8c577a6e46ea8913149e21e959f7 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnc1 | COC=1C=C(C=CC1CN1N=NC=C1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1C=NC=C1>>N1(C=NC=C1)CC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | n1[n:19]([CH2:18][c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[cH:20][cH:21][n:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][n:19]1[cH:20][cH:21][n:22][cH:23]1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnc1 | null | null | null | Functional Group Interconversion | OtherReaction | 3b0a34090ed9e21d704e52bdb53d09d0b025aa5fe0bcd61757484c13def56d74 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2oc(-c3ccc(Cn4ccnc4)cc3)nc2c1 | [c:1]-[C:2]-[n;H0;D3;+0:3]1:[c:4]:[c:5]:[n;H0;D2;+0:6]:n:1>>[c:1]-[C:2]-[n;H0;D3;+0:3]1:[c:4]:[c:5]:[n;H0;D2;+0:6]:[c:7]:1 | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and imidazole (70 mg, 1.0 mmol) afforded the desired 2-[4-(1H-imidazol-1-ylmethyl)-3-methoxyphenyl]-1,3-benzoxazole as a co... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]nn1 | c1c[nH]cn1 | c1ccccc1.c1ccc2ocnc2c1.c1c[nH]cn1 | null | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4461be6f64b94b51bfff28eea4a5d2be | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cccn1 | COC=1C=C(C=CC1CN1N=NC=C1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1N=CC=C1>>COC=1C=C(C=CC1CN1N=CC=C1)C=1OC2=C(N1)C=CC=C2 | n1[cH:21][cH:20][n:19]([CH2:18][c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[n:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][n:19]1[cH:20][cH:21][cH:22][n:23]1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1cccn1 | null | null | null | Functional Group Interconversion | OtherReaction | b9b1573eb5bf3626a9d23b6c9d61df84d8110ce055630390dea167db138dd981 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2oc(-c3ccc(Cn4cccn4)cc3)nc2c1 | [C:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:n:[n;H0;D2;+0:5]:1>>[C:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:[c:6]:[n;H0;D2;+0:5]:1 | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and pyrazole (70 mg, 1.0 mmol) afforded the desired 2-[3-methoxy-4-(1H-pyrazol-1-ylmethyl)phenyl]-1,3-benzoxazole as a colo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]nn1 | c1cn[nH]c1 | c1ccccc1.c1ccc2ocnc2c1.c1cn[nH]c1 | null | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-be02f65dc25f4d68a537d777c24187ef | Brc1c[nH]cn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cnc(Br)c1 | COC=1C=C(C=CC1CN1N=NC=C1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.BrC=1N=CNC1>>BrC=1N=CN(C1)CC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | [nH:19]1[cH:20][n:21][c:22]([Br:23])[cH:24]1.Br[CH2:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][n:19]1[cH:20][n:21][c:22]([Br:... | Brc1c[nH]cn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr | COc1cc(-c2nc3ccccc3o2)ccc1Cn1cnc(Br)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2oc(-c3ccc(Cn4ccnc4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[Br;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[nH;D2;+0:9]:[c:10]:1>>[Br;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[n;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:10]:1 | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 4-bromo-1H-imidazole (150 mg, 1.0 mmol) afforded the desired 2-{4-[(4-bromo-1H-imidazol-1-yl)methyl]-3-methoxyphenyl}-1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccc2ocnc2c1.c1c[nH]cn1 | HBr | null | null | null | Brc1c[nH]cn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cnc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b3841699031464c9e99c4979831a35d | COc1cc(-c2nc3ccccc3o2)ccc1CBr.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1.c1nnn[nH]1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cnnn1.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ncnn1 | COC=1C=C(C=CC1CN1N=NC=C1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1N=NN=C1>>COC=1C=C(C=CC1CN1N=CN=N1)C=1OC2=C(N1)C=CC=C2.COC=1C=C(C=CC1CN1N=NN=C1)C=1OC2=C(N1)C=CC=C2 | Br[CH2:41][c:40]1[c:26]([O:25][CH3:24])[cH:27][c:28](-[c:29]2[n:30][c:31]3[cH:32][cH:33][cH:34][cH:35][c:36]3[o:37]2)[cH:38][cH:39]1.c1[cH:20][n:19]([CH2:18][c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[n:23][n:22]1.[n:21]1[cH:44][nH:42][n:46][n:45]1>... | COc1cc(-c2nc3ccccc3o2)ccc1CBr.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1.c1nnn[nH]1 | COc1cc(-c2nc3ccccc3o2)ccc1Cn1cnnn1.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ncnn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 6556869ff7fd7055b82e1c8db1acaae93aac971737cd641ea0bbc3509d7bdc3e | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2oc(-c3ccc(Cn4cnnn4)cc3)nc2c1.c1ccc2oc(-c3ccc(Cn4ncnn4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]1:[n;H0;D2;+0:6]:[n;H0;D2;+0:7]:[cH;D2;+0:8]:[nH;D2;+0:9]:1.[C:10]-[#7;a:11]1:[#7;a:12]:[n;H0;D2;+0:13]:c:[cH;D2;+0:14]:1>>[C:10]-[#7;a:11]1:[#7;a:12]:[n;H0;D2;+0:13]:[n;H0;D2;+0:7]:[cH;D2;+0:14]:1.[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:15]:[cH;D2;+0:8]:[n;H0;D2;+0... | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 1H-tetrazole (70 mg, 1.0 mmol) afforded 2-[3-methoxy-4-(2H-tetrazol-2-ylmethyl)phenyl]-1,3-benzoxazole and 2-[3-methoxy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]nn1.c1nnn[nH]1 | c1nnn[nH]1.c1nnn[nH]1 | c1ccccc1.c1ccc2ocnc2c1.c1nnn[nH]1.c1ccccc1.c1ccc2ocnc2c1.c1nnn[nH]1 | HBr | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1CBr.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1.c1nnn[nH]1>>COc1cc(-c2nc3ccccc3o2)ccc1Cn1cnnn1.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ncnn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ea58c14c35c4c3c8612cc28c416aaa6 | COC(=O)c1c[nH]cn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COC(=O)c1cn(Cc2ccc(-c3nc4ccccc4o3)cc2OC)cn1.COC(=O)c1cncn1Cc1ccc(-c2nc3ccccc3o2)cc1OC | COC=1C=C(C=CC1CN1N=NC=C1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1C=NC(=C1)C(=O)OC>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(CN1C=NC=C1C(=O)OC)C=C2)OC.O1C(=NC2=C1C=CC=C2)C2=CC(=C(CN1C=NC(=C1)C(=O)OC)C=C2)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:26][n:27]1.Br[CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[o:21]2)[cH:22][c:23]1[O:24][CH3:25].n1[n:34][cH:33][cH:32][n:36]1[CH2:37][c:38]1[cH:39][cH:40][c:41](-[c:42]2[o:29][c:49]3[c:44]([n:43]2)[cH:45][cH:46][cH:47][cH:48]3)[c... | COC(=O)c1c[nH]cn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1 | COC(=O)c1cn(Cc2ccc(-c3nc4ccccc4o3)cc2OC)cn1.COC(=O)c1cncn1Cc1ccc(-c2nc3ccccc3o2)cc1OC | null | null | null | Acylation | OtherReaction | e28f237dbf096eee7efb18d393812c063d24008ce7a5fcbcd2995b3640a952eb | 8a910b6e9517c9f8a7b94355ea68a841bfead1c8ed3de0541c38498810cecc49 | c1ccc2oc(-c3ccc(Cn4ccnc4)cc3)nc2c1.c1ccc2oc(-c3ccc(Cn4ccnc4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1.[c:13]-[C:14]-[n;H0;D3;+0:15]1:[cH;D2;+0:16]:[c:17]:[n;H0;D2;+0:18]:n:1.[c:19]:[c:20](-[c;H0;D3;+0:21]1:[#7;a:22]:[c:23](:[c:24]):[c;H0;D3;+0:25](:[c:26]:[c:27]):[o;H0;D2;+0:28]:1):[c:29]>>[#8:5]-[C:6](=[O;D1;H... | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and methyl 4-imidazole carboxylate (126 mg, 1.0 mmol) afforded methyl 1-[4-(1,3-benzoxazol-2-yl)-2-methoxybenzyl]-1H-imidaz... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | c1c[nH]cn1.c1c[nH]nn1.c1ccc2ocnc2c1 | c1c[nH]cn1.c1c[nH]cn1.c1ccc2ocnc2c1 | c1c[nH]cn1.c1ccccc1.c1ccc2ocnc2c1.c1c[nH]cn1.c1ccccc1.c1ccc2ocnc2c1 | Br- | null | null | null | COC(=O)c1c[nH]cn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr.COc1cc(-c2nc3ccccc3o2)ccc1Cn1ccnn1>>COC(=O)c1cn(Cc2ccc(-c3nc4ccccc4o3)cc2OC)cn1.COC(=O)c1cncn1Cc1ccc(-c2nc3ccccc3o2)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d727bc8a4d84ea78c9269287c4a100c | C1CCNC1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>>COc1cc(-c2nc3ccccc3o2)ccc1CN1CCCC1 | N1CCCC1.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.C(C)N(CC)CC>>COC=1C=C(C=CC1CN1CCCC1)C=1OC2=C(N1)C=CC=C2 | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.Br[CH2:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][N:19]1[CH2:20][CH2:21][CH2:22][CH... | C1CCNC1.COc1cc(-c2nc3ccccc3o2)ccc1CBr | COc1cc(-c2nc3ccccc3o2)ccc1CN1CCCC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2oc(-c3ccc(CN4CCCC4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:4] | null | [] | null | null | 8 | HOUR | Pyrrolidine (226 μL, 2.83 mmol) was added to a stirring solution of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 0.94 mmol) and triethylamine (390 μL, 2.8 mmol) in CH2Cl2 (5 mL). The mixture was stirred at rt overnight. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccc2ocnc2c1.C1CC[NH]C1 | HBr | C(Cl)Cl | null | 8 | C1CCNC1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>C(Cl)Cl>COc1cc(-c2nc3ccccc3o2)ccc1CN1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c59404332d6248c9b8b4adb3a1b959e4 | C1CCNCC1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>>COc1cc(-c2nc3ccccc3o2)ccc1CN1CCCCC1 | COC=1C=C(C=CC1CN1CCCC1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1CCCCC1.C(C)N(CC)CC>>COC=1C=C(C=CC1CN1CCCCC1)C=1OC2=C(N1)C=CC=C2 | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.Br[CH2:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][N:19]1[CH2:20][CH2:21][CH... | C1CCNCC1.COc1cc(-c2nc3ccccc3o2)ccc1CBr | COc1cc(-c2nc3ccccc3o2)ccc1CN1CCCCC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2oc(-c3ccc(CN4CCCCC4)cc3)nc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazole, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 0.942 mmol) was reacted with piperidine (279 μL, 2.83 mmol) and triethylamine (394 μL, 2.83 mmol) in CH2Cl2 (5 mL) to afford the desired 2-[3-methoxy-4... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccc2ocnc2c1.C1CC[NH]CC1 | HBr | C(Cl)Cl | null | null | C1CCNCC1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>C(Cl)Cl>COc1cc(-c2nc3ccccc3o2)ccc1CN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-630d9631f495463896aebb68080e674b | Brc1ccccn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>>COc1cc(-c2nc3ccccc3o2)ccc1Cc1ccccn1 | BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.Cl[Si](C)(C)C.BrC1=NC=CC=C1.BrCCBr>>COC=1C=C(C=CC1CC1=NC=CC=C1)C=1OC2=C(N1)C=CC=C2 | Br[c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1.Br[CH2:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH... | Brc1ccccn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr | COc1cc(-c2nc3ccccc3o2)ccc1Cc1ccccn1 | null | [Zn].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 | C1CCOC1 | C-C Coupling | Negishi | 811c089955cd652ca149ef3c357719b6f0e84d967596883b11590f678c676190 | 84e12b0159f1d183204538a38a0b22f090552039c6c4b4ca4a95700e436c4e5e | c1ccc(Cc2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].Br-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:8]:[c:9]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:8]:[c:9]):[c:4] | null | [] | null | null | null | null | A solution of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (320 mg, 1.0 mmol) and THF (10 mL) was treated with Zn powder (activated by grinding with mortar and pestle), a drop of chlorotrimethylsilane, and a drop of 1,2-dibromoethane. The mixture was heated at reflux for 1 h. The resultant organozinc reagent was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | Br- | [Zn].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.C1CCOC1 | null | null | Brc1ccccn1.COc1cc(-c2nc3ccccc3o2)ccc1CBr>[Zn].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.C1CCOC1>COc1cc(-c2nc3ccccc3o2)ccc1Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a07ed9330a9844e9a2231169eeda2c61 | COc1cc(-c2nc3ccccc3o2)ccc1CBr.OB(O)c1cccnc1>>COc1cc(-c2nc3ccccc3o2)ccc1Cc1cccnc1 | BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1=CC(=CC=C1)B(O)O.C(=O)([O-])[O-].[K+].[K+].COCCOC>>COC=1C=C(C=CC1CC=1C=NC=CC1)C=1OC2=C(N1)C=CC=C2 | Br[CH2:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1.OB(O)[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22]... | COc1cc(-c2nc3ccccc3o2)ccc1CBr.OB(O)c1cccnc1 | COc1cc(-c2nc3ccccc3o2)ccc1Cc1cccnc1 | 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 | O | C-C Coupling | Suzuki coupling with boronic acids | c1d98206ee3e4d9e9b48b8ee3334cc718755db855d367b4791bd268a685f5ef9 | 77bbb9846964762bb5b895814805f25c03261f9c57aae0ecb20ded1ebe6a7af2 | c1cncc(Cc2ccc(-c3nc4ccccc4o3)cc2)c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O-B(-O)-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1):[c:4] | null | [] | 80 | CELSIUS | null | null | A mixture of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (190 mg, 0.58 mmol), 3-pyridylboronic acid (70 mg, 0.58 mmol), Pd(Ph3P)4 (70 mg, 0.06 mmol), K2CO3 (200 mg, 1.5 mmol), DME (6 mL) and H2O (3 mL) was degassed with bubbling Ar for 15 min. The mixture was heated at 80° C. for 1 h. The reaction was poured in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Boronic acid | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 80 | null | COc1cc(-c2nc3ccccc3o2)ccc1CBr.OB(O)c1cccnc1>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.O>COc1cc(-c2nc3ccccc3o2)ccc1Cc1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67c362d7d8234513aa5b88fc8168c706 | COc1cc(-c2nc3ccccc3o2)ccc1Cc1cccnc1.OB(O)c1ccncc1>>COc1cc(-c2nc3ccccc3o2)ccc1Cc1ccncc1 | COC=1C=C(C=CC1CC=1C=NC=CC1)C=1OC2=C(N1)C=CC=C2.BrCC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1=CC=C(C=C1)B(O)O>>COC=1C=C(C=CC1CC1=CC=NC=C1)C=1OC2=C(N1)C=CC=C2 | c1cncc([CH2:18][c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)c1.OB(O)[c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[CH2:18][c:19]1[cH:20][cH:21... | COc1cc(-c2nc3ccccc3o2)ccc1Cc1cccnc1.OB(O)c1ccncc1 | COc1cc(-c2nc3ccccc3o2)ccc1Cc1ccncc1 | null | null | null | C-C Coupling | OtherReaction | 8d32e0b80f6dadcfb16141801165d594f42ebf562fee23ac640a539f10aa5a39 | fb7ad422d905bdc265298a43c871eec14eab0c8cca46cc3d1bd494f2a986d765 | c1ccc2oc(-c3ccc(Cc4ccncc4)cc3)nc2c1 | O-B(-O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[c:7]:[c:8](-[CH2;D2;+0:9]-c1:c:c:c:n:c:1):[c:10]>>[c:7]:[c:8](-[CH2;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | null | [] | null | null | null | null | Utilizing the general procedure outlined for 2-[3-methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazole, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (270 mg, 0.81 mmol), 4-pyridylboronic acid (100 mg, 0.81 mmol) reacted to afford the desired 2-[3-methoxy-4-(pyridin-4-ylmethyl)phenyl]-1,3-benzoxazole as a colorl... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccncc1.c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HO-.B | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1Cc1cccnc1.OB(O)c1ccncc1>>COc1cc(-c2nc3ccccc3o2)ccc1Cc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8cb6b06cc4ed41c8af5693e089fd16b2 | C1COCCN1.O=CCc1ccc(-c2nc3ccccc3o2)cc1Cl>>Clc1cc(-c2nc3ccccc3o2)ccc1CCN1CCOCC1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)CC=O)Cl.[BH3-]C#N.[Na+].N1CCOCC1>>ClC=1C=C(C=CC1CCN1CCOCC1)C=1OC2=C(N1)C=CC=C2 | [NH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1.O=[CH:18][CH2:17][c:16]1[c:2]([Cl:1])[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15]1>>[Cl:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15][c:16]1[CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][O:2... | C1COCCN1.O=CCc1ccc(-c2nc3ccccc3o2)cc1Cl | Clc1cc(-c2nc3ccccc3o2)ccc1CCN1CCOCC1 | null | null | CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | 073d98e7dcd77aafeef71a76da7e61b2751c934600f6fff04db700a08f3e4453 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc2oc(-c3ccc(CCN4CCOCC4)cc3)nc2c1 | O=[CH;D2;+0:1]-[C:2]-[c:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[c:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | The crude aldehyde was treated with NaCNBH3 and morpholine in MeOH/CH2Cl2 (2 mL). The crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 2-[3-chloro-4-(2-morpholin-4-ylethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 8.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1ccc2ocnc2c1.C1COCC[NH]1 | Other | CO.C(Cl)Cl | null | null | C1COCCN1.O=CCc1ccc(-c2nc3ccccc3o2)cc1Cl>CO.C(Cl)Cl>Clc1cc(-c2nc3ccccc3o2)ccc1CCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0ce9b91068f4bcba8b532f68bbc557c | Cc1cc(C(=O)O)ccc1Br.Nc1ccccc1O>>Cc1cc(-c2nc3ccccc3o2)ccc1Br | NC1=C(C=CC=C1)O.BrC1=C(C=C(C(=O)O)C=C1)C>>BrC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)C | O=[C:5](O)[c:4]1[cH:3][c:2]([CH3:1])[c:16]([Br:17])[cH:15][cH:14]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[OH:13]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15][c:16]1[Br:17] | Cc1cc(C(=O)O)ccc1Br.Nc1ccccc1O | Cc1cc(-c2nc3ccccc3o2)ccc1Br | 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:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | 200 | CELSIUS | 8 | HOUR | Polyphosphoric acid (100 mL) was added to a beaker containing 2-aminophenol (17.7 g, 162 mmol) and 4-bromo-3-methylbenzoic acid (13.6 g, 64 mmol). The mixture was heated at 200° C. for 1 h, then poured into ice water (1 L) and allowed to stand overnight. The mixture was filtered and dried to afford 2-(4-bromo-3-methyl(... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | null | 200 | 8 | Cc1cc(C(=O)O)ccc1Br.Nc1ccccc1O>>Cc1cc(-c2nc3ccccc3o2)ccc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee22159b05ea4983a1a5e185d2a70e74 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.Cc1cc(-c2nc3ccccc3o2)ccc1Br>>Cc1cc(-c2nc3ccccc3o2)ccc1-c1ccccn1 | BrC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)C.C(CCC)[Sn](C1=NC=CC=C1)(CCCC)CCCC.CN(C)C=O.[F-].[K+]>>CC=1C=C(C=CC1C1=NC=CC=C1)C=1OC2=C(N1)C=CC=C2 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1.Br[c:16]1[c:2]([CH3:1])[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][cH:20]... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.Cc1cc(-c2nc3ccccc3o2)ccc1Br | Cc1cc(-c2nc3ccccc3o2)ccc1-c1ccccn1 | 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 | O | C-C Coupling | Stille reaction_aryl | ce918bbb171f9e7bd99035931c043f0f33f636d165d8c0e73629d8717d6c595a | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | null | [] | 100 | CELSIUS | null | null | Polyphosphoric acid (100 mL) was added to a beaker containing 2-aminophenol (17.7 g, 162 mmol) and 4-bromo-3-methylbenzoic acid (13.6 g, 64 mmol). The mixture was heated at 200° C. for 1 h, then poured into ice water (1 L) and allowed to stand overnight. The mixture was filtered and dried to afford 2-(4-bromo-3-methyl(... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr.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.O | 100 | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.Cc1cc(-c2nc3ccccc3o2)ccc1Br>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.O>Cc1cc(-c2nc3ccccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5491a6e17264b91ba9e8509c39cb5aa | COc1cc(C(=O)O)ccc1O.Nc1ccccc1O>>COc1cc(-c2nc3ccccc3o2)ccc1O | OC1=C(C=C(C(=O)O)C=C1)OC.NC1=C(C=CC=C1)O>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)O)OC | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([OH:18])[cH:16][cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[OH:18] | COc1cc(C(=O)O)ccc1O.Nc1ccccc1O | COc1cc(-c2nc3ccccc3o2)ccc1O | null | null | C[Si](C)(C)OP(=O)=O | 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:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | 180 | CELSIUS | 8 | HOUR | 4-hydroxy-3-methoxybenzoic acid (25 g, 149 mmol) and 2-amino phenol (16.2 g, 149 mmol) were combined in a round bottom flask. Trimethylsilyl polyphosphate (80 mL) was added neat. The mixture was heated at 180° C. for 30 min. The mixture is poured over ice and allowed to stir overnight. The suspension was filtered to af... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C[Si](C)(C)OP(=O)=O | 180 | 8 | COc1cc(C(=O)O)ccc1O.Nc1ccccc1O>C[Si](C)(C)OP(=O)=O>COc1cc(-c2nc3ccccc3o2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2020d595bac54db7a0e79c46a313ea81 | COC(=O)c1ccc(OC)c(C#N)c1>>COc1ccc(C(=O)O)cc1C#N | Cl.C(#N)C=1C=C(C(=O)OC)C=CC1OC.[Li+].[OH-]>>C(#N)C=1C=C(C(=O)O)C=CC1OC | C[O:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([C:12]#[N:13])[cH:10]1)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[C:12]#[N:13] | COC(=O)c1ccc(OC)c(C#N)c1 | COc1ccc(C(=O)O)cc1C#N | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | To a solution of methyl 3-cyano-4-methoxy-benzoate (1.5 g, 7.9 mmol) in CH3OH/H2O (25 mL; 1:1), was added LiOH (2.5 g, 60.0 mmol). The reaction mixture was refluxed for 2 h, cooled at rt and 6M HCl was added dropwise until pH 2 was obtained. The precipitate was collected, washed with H2O (3×20 mL), dried in vacuo to af... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO.O | null | null | COC(=O)c1ccc(OC)c(C#N)c1>CO.O>COc1ccc(C(=O)O)cc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43b89c92a2b543e48b4da1a4e02abf86 | COc1ccc(C(=O)O)cc1C#N.Nc1ccccc1O>>COc1ccc(-c2nc3ccccc3o2)cc1C#N | NC1=C(C=CC=C1)O.C(C)N(CC)CC.C(#N)C=1C=C(C(=O)O)C=CC1OC.O=S(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C#N)C2)OC | O=[C:7](O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([C:18]#[N:19])[cH:16]1.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][c:17]1[C:18]#[N:19] | COc1ccc(C(=O)O)cc1C#N.Nc1ccccc1O | COc1ccc(-c2nc3ccccc3o2)cc1C#N | null | null | C1CCOC1.CCOC(=O)C | 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 | 3 | HOUR | To a solution of methyl 3-cyano-4-methoxy-benzoate (1.5 g, 7.9 mmol) in CH3OH/H2O (25 mL; 1:1), was added LiOH (2.5 g, 60.0 mmol). The reaction mixture was refluxed for 2 h, cooled at rt and 6M HCl was added dropwise until pH 2 was obtained. The precipitate was collected, washed with H2O (3×20 mL), dried in vacuo to af... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1CCOC1.CCOC(=O)C | null | 3 | COc1ccc(C(=O)O)cc1C#N.Nc1ccccc1O>C1CCOC1.CCOC(=O)C>COc1ccc(-c2nc3ccccc3o2)cc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d520da0a211748ddab0429d699c7af31 | COc1ccc(-c2nc3ccccc3o2)cc1C#N>>N#Cc1cc(-c2nc3ccccc3o2)ccc1O | O.CCOC(=O)C.O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C#N)C2)OC.B(Br)(Br)Br>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C#N)C2)O | C[O:18][c:17]1[c:3]([C:2]#[N:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[OH:18] | COc1ccc(-c2nc3ccccc3o2)cc1C#N | N#Cc1cc(-c2nc3ccccc3o2)ccc1O | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nc3ccccc3o2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4 | HOUR | To a solution of 5-(1,3-benzoxazol-2-yl)-2-methoxy benzonitrile (270 mg, 1.1 mmol) in CH2Cl2 (5 mL) at 0° C., was added BBr3 (1.0M solution in CH2Cl2, 430 μL, 4.4 mmol) dropwise. The reaction was stirred at it for 4 h. EtOAc (150 mL) was added, as well as H2O (30 mL). The organic layer was washed with brine (2×20 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2ocnc2c1 | Other | C(Cl)Cl | null | 4 | COc1ccc(-c2nc3ccccc3o2)cc1C#N>C(Cl)Cl>N#Cc1cc(-c2nc3ccccc3o2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b86ba7fc6984a3c8299ef5961aa3279 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.N#Cc1cc(-c2nc3ccccc3o2)ccc1OS(=O)(=O)C(F)(F)F>>N#Cc1cc(-c2nc3ccccc3o2)ccc1-c1ccccn1 | FC(S(=O)(=O)OC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)C#N)(F)F.C(CCC)[Sn](C1=NC=CC=C1)(CCCC)CCCC.CCOC(=O)C>>O1C(=NC2=C1C=CC=C2)C=2C=CC(=C(C#N)C2)C2=NC=CC=C2 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1.O=S(=O)(O[c:17]1[c:3]([C:2]#[N:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1)C(F)(F)F>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.N#Cc1cc(-c2nc3ccccc3o2)ccc1OS(=O)(=O)C(F)(F)F | N#Cc1cc(-c2nc3ccccc3o2)ccc1-c1ccccn1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC.[Cl-].[Na+].O | C-C Coupling | Stille reaction_aryl OTf | 9a2cde59545d713d5c04f237272577dd9739a9dce6288d3e9fff794ae95d6d15 | 46de4d1253710b3a7d4f46887df51b2ccba46e0a9427959558bd6f96ec8696eb | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10]#[N;D1;H0:11]):[c:12]>>[N;D1;H0:11]#[C:10]-[c:9](:[c:12]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | 90 | CELSIUS | 8 | HOUR | The degassed solution of 4-(1,3-benzoxazol-2-yl)-2-cyanophenyl trifluoromethanesulfonate (300 mg, 1.2 mmol) in DME (5 mL) was added 2-tri-n-butylstannylpyridine (273 mg, 0.74 mmol), tetrakis(triphenylphosphine)palladium(0) (150 mg, 0.1 mmol). The reaction was stirred at 90° C. overnight and cooled to rt. EtOAc (100 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Tin | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | TfOH.HO-.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.COCCOC.[Cl-].[Na+].O | 90 | 8 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccccn1.N#Cc1cc(-c2nc3ccccc3o2)ccc1OS(=O)(=O)C(F)(F)F>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.[Cl-].[Na+].O>N#Cc1cc(-c2nc3ccccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e752cd1bb8744e3a7f516e7c7fa0f3a | COc1cc(-c2nc3ccccc3o2)ccc1OS(=O)(=O)C(F)(F)F.OB(O)c1cccnc1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccnc1 | C(=O)([O-])[O-].[K+].[K+].N1=CC(=CC=C1)B(O)O.FC(S(=O)(=O)OC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC)(F)F.O>>COC=1C=C(C=CC1C=1C=NC=CC1)C=1OC2=C(N1)C=CC=C2 | O=S(=O)(O[c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1)C(F)(F)F.OB(O)[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21... | COc1cc(-c2nc3ccccc3o2)ccc1OS(=O)(=O)C(F)(F)F.OB(O)c1cccnc1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccnc1 | null | [N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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 | CN(C)C=O | C-C Coupling | Suzuki coupling with boronic acids OTf | c38f4e60d1ae6c38b2f197a2af78f3c5a2df5e4d90f29be3c1cc7356f21f0737 | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1cncc(-c2ccc(-c3nc4ccccc4o3)cc2)c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1):[c:2]:[c:3] | null | [] | 75 | CELSIUS | null | null | The solution of 4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl trifluoromethanesulfonate (148 mg, 0.4 mmol) in 6 mL of 2:1 DMF:H2O was degassed via Argon for 10 min. Then K2CO3 (137 mg, 0.99 mmol), Pd(Ph3P)4 (23 mg, 0.02 mmol), n-Bu4NBr (128 mg, 0.40 mmol) and 3-Pyridylboronic acid (73 mg, 0.60 mmol) were added at 22° C. The ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | TfOH.HO-.B | [N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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.CN(C)C=O | 75 | null | COc1cc(-c2nc3ccccc3o2)ccc1OS(=O)(=O)C(F)(F)F.OB(O)c1cccnc1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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.CN(C)C=O>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94875554872641b68a779e43dbc5acbf | Nc1ccccc1O.O=C(O)c1ccc(O)c(Cl)c1>>O=C(Nc1ccccc1)c1ccc(Cl)c(O)c1 | ClC=1C=C(C(=O)O)C=CC1O.C(C(=O)Cl)(=O)Cl.NC1=C(C=CC=C1)O.CN(C)C=O>>ClC1=C(C=C(C(=O)NC2=CC=CC=C2)C=C1)O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:16].O[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13](O)[c:15]([Cl:14])[cH:17]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([OH:16])[cH:17]1 | Nc1ccccc1O.O=C(O)c1ccc(O)c(Cl)c1 | O=C(Nc1ccccc1)c1ccc(Cl)c(O)c1 | null | null | ClCCl | Acylation | OtherReaction | 38c8ecf330948f768d5f0a3a14303307f2e11bdb1eeb0ef61dc175e0810a2c98 | 8dc1dc48a929880b2a650616ab3487608333342c43c9c31384a4d3fd8bfba048 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-O):[c;H0;D3;+0:7](-[Cl;H0;D1;+0:8]):[c:9]:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](-[OH;D1;+0:14]):[c:15]:[c:16]>>[Cl;H0;D1;+0:8]-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:15]:[... | null | [] | null | null | 2 | HOUR | A suspension of 3-chloro-4-hydroxybenzoic acid (20.0 g, 11.6 mmol) in anhydrous dichloromethane (100 mL) was treated with oxalyl chloride (20 mL, 23.2 mmol) followed by few drops of DMF at 22° C. under argon. After 2 h stirring, the solution became clear, concentrated to dryness, dissolved in dichloromethane (50 mL) an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Aromatic alcohol.Aromatic alcohol.Primary amine | Aromatic halide.Secondary amide.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 2 | Nc1ccccc1O.O=C(O)c1ccc(O)c(Cl)c1>ClCCl>O=C(Nc1ccccc1)c1ccc(Cl)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d2bf357927e4ef08780c9b0afbd39d0 | O=S(=O)(Oc1ccc(-c2nc3ccccc3o2)cc1Cl)C(F)(F)F.OB(O)c1cccnc1>>Clc1cc(-c2nc3ccccc3o2)ccc1-c1cccnc1 | C(=O)([O-])[O-].[K+].[K+].N1=CC(=CC=C1)B(O)O.FC(S(=O)(=O)OC1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)Cl)(F)F.O>>ClC=1C=C(C=CC1C=1C=NC=CC1)C=1OC2=C(N1)C=CC=C2 | O=S(=O)(O[c:16]1[c:2]([Cl:1])[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15]1)C(F)(F)F.OB(O)[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[Cl:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]... | O=S(=O)(Oc1ccc(-c2nc3ccccc3o2)cc1Cl)C(F)(F)F.OB(O)c1cccnc1 | Clc1cc(-c2nc3ccccc3o2)ccc1-c1cccnc1 | null | [N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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 | CN(C)C=O | C-C Coupling | Suzuki coupling with boronic acids OTf | c38f4e60d1ae6c38b2f197a2af78f3c5a2df5e4d90f29be3c1cc7356f21f0737 | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1cncc(-c2ccc(-c3nc4ccccc4o3)cc2)c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1):[c:2]:[c:3] | null | [] | 75 | CELSIUS | null | null | A suspension of 3-chloro-4-hydroxybenzoic acid (20.0 g, 11.6 mmol) in anhydrous dichloromethane (100 mL) was treated with oxalyl chloride (20 mL, 23.2 mmol) followed by few drops of DMF at 22° C. under argon. After 2 h stirring, the solution became clear, concentrated to dryness, dissolved in dichloromethane (50 mL) an... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | TfOH.HO-.B | [N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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.CN(C)C=O | 75 | null | O=S(=O)(Oc1ccc(-c2nc3ccccc3o2)cc1Cl)C(F)(F)F.OB(O)c1cccnc1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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.CN(C)C=O>Clc1cc(-c2nc3ccccc3o2)ccc1-c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba8606b425c74166b50320df786dbb82 | COC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)c(OC)c1.[Zn+][c]1ccccn1>>COC(=O)c1ccc(-c2ccccn2)c(OC)c1 | COC=1C=C(C(=O)OC)C=CC1OS(=O)(=O)C(F)(F)F.[Br-].N1=C(C=CC=C1)[Zn+]>>COC=1C=C(C(=O)OC)C=CC1C1=NC=CC=C1 | O=S(=O)(O[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][c:15]1[O:16][CH3:17])C(F)(F)F.[Zn+][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[c:15]([O:16][CH3:17])[cH:18]1 | COC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)c(OC)c1.[Zn+][c]1ccccn1 | COC(=O)c1ccc(-c2ccccn2)c(OC)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 | C1CCOC1 | C-C Coupling | OtherReaction | 97b8e71ebe9ec09e0177bbabe2aa72e22f1d29bf116a7bddda068b125d18b6c4 | 253c3b9fccee9bf420e0fb1f267e37bad5aa0c206427cb57447e420babcc09c8 | c1ccc(-c2ccccn2)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[Zn+]-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | To 300 mL of degassed THF was added methyl 3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (20.95 g, 66.7 mmol), 2-pyridylzinc bromide (200 mL of 0.5M solution in THF, 100 mmol), and tetrakis(triphenylphosphine)palladium(0) (5.00 g, 4.3 mmol). The mixture was degassed with argon for an additional 30 minutes and he... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | TfOH.Zn | 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.C1CCOC1 | null | null | COC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)c(OC)c1.[Zn+][c]1ccccn1>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.C1CCOC1>COC(=O)c1ccc(-c2ccccn2)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-78f9376cc45a4226aebdcbd7db6399c9 | COC(=O)c1ccc(-c2ccccn2)c(OC)c1>>COc1cc(C(=O)O)ccc1-c1ccccn1 | COC=1C=C(C(=O)OC)C=CC1C1=NC=CC=C1.Cl.CO.O.[OH-].[Li+].Cl>>COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1 | C[O:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[cH:10][cH:9]1)=[O:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1-[c:12]1[cH:13][cH:14][cH:15][cH:16][n:17]1 | COC(=O)c1ccc(-c2ccccn2)c(OC)c1 | COc1cc(C(=O)O)ccc1-c1ccccn1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | To 154 mL of a 50/50 solution of MeOH and H2O was added lithium hydroxide monohydrate (13.85 g, 330 mmol). The solution was stirred until all of the salt dissolved, at which point methyl 3-methoxy-4-pyridin-2-ylbenzoate (8.02 g, 32.9 mmol) was added. The mixture was heated at reflux and stirred overnight. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | O | null | null | COC(=O)c1ccc(-c2ccccn2)c(OC)c1>O>COc1cc(C(=O)O)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-155edca81d244fa58d3afef51264be52 | O=[N+]([O-])c1cc(F)ccc1O>>Nc1cc(F)ccc1O | C(=O)(O)[O-].[Na+].FC1=CC(=C(C=C1)O)[N+](=O)[O-].O.O.[Sn](Cl)Cl>>NC1=C(C=CC(=C1)F)O | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[OH:9]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[OH:9] | O=[N+]([O-])c1cc(F)ccc1O | Nc1cc(F)ccc1O | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a stirred solution of 4-fluoro-2-nitrophenol (4.05 g, 25.8 mmol) in MeOH (200 mL) was added tin(II) chloride dihydrate (17.47 g, 77.4 mmol). The reaction mixture was heated at reflux and monitored by LC/MS. When significant reduction was complete, the reaction mixture was cooled to rt, poured over ice, and made basi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CO | null | null | O=[N+]([O-])c1cc(F)ccc1O>CO>Nc1cc(F)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90f5ba66db5b4dc8a2014e6adc3abaca | O=[N+]([O-])c1cc(Br)cc(F)c1O>>Nc1cccc(F)c1O | BrC1=CC(=C(C(=C1)[N+](=O)[O-])O)F>>NC1=C(C(=CC=C1)F)O | O=[N+:1]([O-])[c:2]1[cH:3][c:4](Br)[cH:5][c:6]([F:7])[c:8]1[OH:9]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[OH:9] | O=[N+]([O-])c1cc(Br)cc(F)c1O | Nc1cccc(F)c1O | null | [Pd] | CO | Reduction | OtherReaction | 1e8d7f084acb021d05db0e4c77f2fa294c6443326e89f172bb6de75e7eecf2f2 | 7a1074c91f17781b9c7c26911e795314b42511dc69433b1dc4bc93ccba503456 | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[N+;H0;D3:4](=O)-[O-]):[c:5]:[c:6]:[c:7]:1>>[NH2;D1;+0:4]-[c:3]1:[c:2]:[cH;D2;+0:1]:[c:7]:[c:6]:[c:5]:1 | null | [] | null | null | null | null | To a stirred slurry of 10% palladium on carbon (2.26 g, 2.12 mmol) in MeOH (100 mL) was added 4-bromo-2-fluoro-6-nitrophenol (5.00 g, 21.2 mmol). The reaction mixture was stirred under an H2 atmosphere until significant reduction was seen by TLC. The mixture was filtered through Celite and concentrated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | [Pd].CO | null | null | O=[N+]([O-])c1cc(Br)cc(F)c1O>[Pd].CO>Nc1cccc(F)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9836977a6c9943028d1255113ebbcc1a | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cccc(F)c1O>>COc1cc(-c2nc3cccc(F)c3o2)ccc1-c1ccccn1 | Cl.C[Si](C)(C)OP(=O)=O.NC1=C(C(=CC=C1)F)O.COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1>>Cl.FC1=CC=CC=2N=C(OC21)C2=CC(=C(C=C2)C2=NC=CC=C2)OC | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[cH:17][cH:16]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]3[o:15]2)[cH:16][cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22][c... | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cccc(F)c1O | COc1cc(-c2nc3cccc(F)c3o2)ccc1-c1ccccn1 | null | null | CCOCC | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | 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:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | 200 | CELSIUS | null | null | To 7 mL trimethylsilyl polyphosphate was added 2-amino-6-fluorophenol (166 mg, 1.31 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (300 mg, 1.31 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with EtOAc (3×150 mL). The combined o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HO- | CCOCC | 200 | null | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cccc(F)c1O>CCOCC>COc1cc(-c2nc3cccc(F)c3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c8eb1ab15de24a91a8d47e2209a31578 | O=[N+]([O-])c1cc(Br)ccc1O>>Nc1cc(Br)ccc1O | C(=O)(O)[O-].[Na+].BrC1=CC(=C(C=C1)O)[N+](=O)[O-].O.O.[Sn](Cl)Cl>>NC1=C(C=CC(=C1)Br)O | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[OH:9]>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[OH:9] | O=[N+]([O-])c1cc(Br)ccc1O | Nc1cc(Br)ccc1O | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a stirred solution of 4-bromo-2-nitrophenol (5.00 g, 22.9 mmol) in MeOH (120 mL) was added tin(II) chloride dihydrate (15.53 g, 68.8 mmol). The reaction mixture was heated at reflux and monitored by LC/MS. When significant reduction was complete, the reaction mixture was cooled to rt, poured over ice, and made basic... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CO | null | null | O=[N+]([O-])c1cc(Br)ccc1O>CO>Nc1cc(Br)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b561074befdb46c6a83752150344d90c | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cc(Br)ccc1O>>COc1cc(-c2nc3cc(Br)ccc3o2)ccc1-c1ccccn1 | NC1=C(C=CC(=C1)Br)O.COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1>>BrC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C2=NC=CC=C2)OC)C1 | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[cH:17][cH:16]1.[NH2:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22]... | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cc(Br)ccc1O | COc1cc(-c2nc3cc(Br)ccc3o2)ccc1-c1ccccn1 | null | null | C[Si](C)(C)OP(=O)=O | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | 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:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | 200 | CELSIUS | null | null | To 20 mL trimethylsilyl polyphosphate was added 2-amino-4-bromophenol (752 mg, 4.00 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (916 mg, 4.00 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with MTBE (3×300 mL). The combined or... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HO- | C[Si](C)(C)OP(=O)=O | 200 | null | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cc(Br)ccc1O>C[Si](C)(C)OP(=O)=O>COc1cc(-c2nc3cc(Br)ccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc5c21bbd0c14b558d315caa0f22ae81 | COc1cc(-c2nc3cc(Br)ccc3o2)ccc1-c1ccccn1>>COc1cc(-c2nc3cc(C#N)ccc3o2)ccc1-c1ccccn1 | BrC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C2=NC=CC=C2)OC)C1.CN(C)C=O>>C(#N)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C2=NC=CC=C2)OC)C1 | Br[c:10]1[cH:9][c:8]2[n:7][c:6](-[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:19](-[c:20]4[cH:21][cH:22][cH:23][cH:24][n:25]4)[cH:18][cH:17]3)[o:16][c:15]2[cH:14][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14][c:15]3[o:16]2)[cH:17][cH:18][c:19]1-[c:20]1[cH:21][cH:22][cH:23][cH:2... | COc1cc(-c2nc3cc(Br)ccc3o2)ccc1-c1ccccn1 | COc1cc(-c2nc3cc(C#N)ccc3o2)ccc1-c1ccccn1 | null | [C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | null | Miscellaneous | OtherReaction | 73f4aa469a93e26fab7e4ca3b6ce92db34cec410520eb7f275adc8b97a86e956 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#8;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:1>>[N;D1;H0:10]#[C:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#8;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:1 | null | [] | 120 | CELSIUS | 8 | HOUR | To 1 mL of degassed DMF was added 5-bromo-2-(3-methoxy-4-pyridin-2-ylphenyl)-1,3-benzoxazole (622 mg, 1.63 mmol), zinc cyanide (115 mg, 0.98 mmol), tris(dibenzylideneacetone)-dipalladium (0)-chloroform complex (30 mg, 0.029 mmol), and 1,1′-bisdiphenylphosphinoferrocene (41 mg, 0.073 mmol). The reaction mixture was dega... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | Br- | [C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | 120 | 8 | COc1cc(-c2nc3cc(Br)ccc3o2)ccc1-c1ccccn1>[C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2]>COc1cc(-c2nc3cc(C#N)ccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14747b92927c4a008bd0c9dd2379904e | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cc(Cl)ccc1O>>COc1cc(-c2nc3cc(Cl)ccc3o2)ccc1-c1ccccn1 | COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1.NC1=C(C=CC(=C1)Cl)O>>ClC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C2=NC=CC=C2)OC)C1 | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[cH:17][cH:16]1.[NH2:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22]... | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cc(Cl)ccc1O | COc1cc(-c2nc3cc(Cl)ccc3o2)ccc1-c1ccccn1 | null | null | O | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | 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:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | null | null | 3-Methoxy-4-pyridin-2-yl benzoic acid (500 mg, 2.2 mmol), 2-amino-4-chlorophenol (620 mg, 4.3 mmol) and trimethyl silylpolyphosphate (2 mL) was heated to 180° C. overnight under argon. To the cooled reaction mixture, water (100 mL) was added and extracted with EtOAc (4×20 mL). Set aside organic layer. Filtered aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HO- | O | null | null | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cc(Cl)ccc1O>O>COc1cc(-c2nc3cc(Cl)ccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d51a620251244c06bff5500e31331620 | Cl>>Cl | ClC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C2=NC=CC=C2)OC)C1.Cl>>Cl.ClC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C2=NC=CC=C2)OC)C1 | [ClH:25]>>[ClH:25] | Cl | Cl | null | null | ClCCl.C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 30 | MINUTE | 5-Chloro-2-(3-methoxy-4-pyridin-2-ylphenyl)-1,3-benzoxazole (26 mg) was stirred in dichloromethane. 1.0M HCl in diethyl ether (0.95 mL) was added and allowed reaction mixture to stir for 30 minutes. Concentration of reaction mixture in vacuo gave the desired compound, 5-chloro-2-(3-methoxy-4-pyridin-2-yl phenyl)-1,3-be... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | ClCCl.C(C)OCC | null | 0.5 | Cl>ClCCl.C(C)OCC>Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86e77d526c46462e8910b6c132f7f41f | COc1cc(C(=O)O)ccc1-c1ccccn1.Cc1ccc(O)c(N)c1>>COc1cc(-c2nc3cc(C)ccc3o2)ccc1-c1ccccn1 | C(=O)(O)[O-].[Na+].COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1.NC1=CC(=CC=C1O)C.C[Si](C)(C)OP(=O)=O>>COC=1C=C(C=CC1C1=NC=CC=C1)C=1OC2=C(N1)C=C(C=C2)C | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[cH:17][cH:16]1.[NH2:7][c:8]1[cH:9][c:10]([CH3:11])[cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][c:10]([CH3:11])[cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:2... | COc1cc(C(=O)O)ccc1-c1ccccn1.Cc1ccc(O)c(N)c1 | COc1cc(-c2nc3cc(C)ccc3o2)ccc1-c1ccccn1 | null | null | O | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | 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:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | null | null | 3-Methoxy-4-pyridin-2-yl benzoic acid (490 mg, 2.1 mmol), 2-amino-p-cresol (527 mg, 4.28 mmol) and trimethylsilyl polyphosphate (2 mL) was refluxed overnight under argon. Added water (100 mL) to the cooled reaction mixture and basified to pH 8 (solid NaHCO3). Extracted with EtOAc (3×60 mL), dried (Na2SO4) and concentra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HO- | O | null | null | COc1cc(C(=O)O)ccc1-c1ccccn1.Cc1ccc(O)c(N)c1>O>COc1cc(-c2nc3cc(C)ccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-734dde27881f45738c88ee15ff6f7b45 | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1ncccc1O>>COc1cc(-c2nc3ncccc3o2)ccc1-c1ccccn1 | C[Si](C)(C)OP(=O)=O.NC1=NC=CC=C1O.COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1>>COC=1C=C(C=CC1C1=NC=CC=C1)C=1OC=2C(=NC=CC2)N1 | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][n:23]2)[cH:16][cH:15]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[n:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1 | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1ncccc1O | COc1cc(-c2nc3ncccc3o2)ccc1-c1ccccn1 | null | null | null | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | a070d4bbe848c5c302d9a11e414aef5399f3e53373b6b4721e984bea2f224fef | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2ccc(-c3nc4ncccc4o3)cc2)nc1 | 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 | [] | 200 | CELSIUS | null | null | To 5 mL of trimethylsilyl polyphosphate was added 2-aminopyridin-3-ol (175 mg, 1.59 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (344 mg, 1.50 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with MTBE (3×200 mL). The combined or... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccncc1 | c1cnc2ncoc2c1 | c1ccccc1.c1cnc2ncoc2c1.c1ccncc1 | HO- | null | 200 | null | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1ncccc1O>>COc1cc(-c2nc3ncccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-640654338223404497e09faf1387ac75 | CC(C)(C)C(=O)Cl.Nc1cccnc1>>CC(C)(C)C(=O)Nc1cccnc1 | NC=1C=NC=CC1.C(C)N(CC)CC.CC(C(=O)Cl)(C)C>>N1=CC(=CC=C1)NC(C(C)(C)C)=O | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1 | CC(C)(C)C(=O)Cl.Nc1cccnc1 | CC(C)(C)C(=O)Nc1cccnc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | null | [] | null | null | 8 | HOUR | To a stirred solution of 3-aminopyridine (9.41 g, 100 mmol) and triethylamine (16.7 mL, 120 mmol) in CH2Cl2 (300 mL) at 0° C. was added trimethylacetyl chloride (14.8 mL, 120 mmol) dropwise over 15 min. The reaction was warmed to rt and stirred overnight. The mixture was concentrated in vacuo, the residue partitioned b... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | 8 | CC(C)(C)C(=O)Cl.Nc1cccnc1>C(Cl)Cl>CC(C)(C)C(=O)Nc1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41a9e16aa1e4461f9bed0abe910ce2eb | CC(C)(C)C(=O)Nc1cccnc1.OO>>CC(C)(C)C(=O)Nc1cnccc1O | CC(=O)O.N1=CC(=CC=C1)NC(C(C)(C)C)=O.C(CCC)[Li].B(OC)(OC)OC.OO>>OC1=C(C=NC=C1)NC(C(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][n:10][cH:11][cH:12][cH:13]1.O[OH:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][n:10][cH:11][cH:12][c:13]1[OH:14] | CC(C)(C)C(=O)Nc1cccnc1.OO | CC(C)(C)C(=O)Nc1cnccc1O | null | null | C1CCOC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 1d486e404d15e1f03f247400e5680334f540a293783abe66ffa8f2f1b3c56e68 | a2fdf414569b219d462bc05c91ebf31e5426b96645f5c78cb091f50cc92fc345 | c1ccncc1 | O-[OH;D1;+0:1].[O;D1;H0:2]=[C:3]-[#7:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[O;D1;H0:2]=[C:3]-[#7:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c;H0;D3;+0:10]:1-[OH;D1;+0:1] | null | [] | 0 | CELSIUS | 3 | HOUR | To a stirred solution of N-(pyridin-3-yl)-2,2-dimethylpropanamide (8.90 g, 50.0 mmol) in THF (200 mL) at −78° C. was added n-Butyllithium (50 mL, 125 mmol) dropwise over 30 min. After addition, the reaction mixture was warmed to 0° C. and stirred an additional 3 h. The reaction was then cooled back to −78° C. and trime... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Aromatic alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | C1CCOC1.O | 0 | 3 | CC(C)(C)C(=O)Nc1cccnc1.OO>C1CCOC1.O>CC(C)(C)C(=O)Nc1cnccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66bdbd2e29424c5a85410be355427813 | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cnccc1O>>COc1cc(-c2nc3cnccc3o2)ccc1-c1ccccn1 | C[Si](C)(C)OP(=O)=O.NC=1C=NC=CC1O.COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1>>COC=1C=C(C=CC1C1=NC=CC=C1)C=1OC2=C(C=NC=C2)N1 | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][n:23]2)[cH:16][cH:15]1.[NH2:7][c:8]1[cH:9][n:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][n:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1 | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cnccc1O | COc1cc(-c2nc3cnccc3o2)ccc1-c1ccccn1 | null | null | null | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | f1ee0623f89591c64914b9a616c22941df6c66bc5f0884963726f04a767da2e3 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2ccc(-c3nc4cnccc4o3)cc2)nc1 | 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]1:[c:9]:[#7;a:10]:[c:11]:[c:12]:[c:13]:1-[OH;D1;+0:14]>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c:8]2:[c:9]:[#7;a:10]:[c:11]:[c:12]:[c:13]:2:[o;H0;D2;+0:14]:1):[c:5]:[c:6] | null | [] | 200 | CELSIUS | null | null | To 7 mL trimethylsilyl polyphosphate was added 3-aminopyridin-4-ol (330 mg, 3.00 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (460 mg, 2.00 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with MTBE (3×200 mL). The combined organ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccncc1 | c1cc2ocnc2cn1 | c1ccccc1.c1cc2ocnc2cn1.c1ccncc1 | HO- | null | 200 | null | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cnccc1O>>COc1cc(-c2nc3cnccc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-be8c3b92fc5f4f4dbb28ec056f335f02 | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cccnc1O>>COc1cc(-c2nc3cccnc3o2)ccc1-c1ccccn1 | C[Si](C)(C)OP(=O)=O.NC=1C(=NC=CC1)O.COC=1C=C(C(=O)O)C=CC1C1=NC=CC=C1>>COC=1C=C(C=CC1C1=NC=CC=C1)C=1OC2=NC=CC=C2N1 | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][n:23]2)[cH:16][cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][n:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1 | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cccnc1O | COc1cc(-c2nc3cccnc3o2)ccc1-c1ccccn1 | null | null | null | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | 466d3d0538d87ca0fd30e69dd344a571d3b9d57b1eb0eef577781913e1f851b4 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc(-c2ccc(-c3nc4cccnc4o3)cc2)nc1 | 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]):[#7;a:12]:[c:13]>>[c:13]:[#7;a:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | 200 | CELSIUS | null | null | To 5 mL of trimethylsilyl polyphosphate was added 3-aminopyridin-2-ol (150 mg, 1.59 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (229 mg, 1.0 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with EtOAc (3×200 mL). The combined or... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccncc1 | c1cnc2ocnc2c1 | c1ccccc1.c1cnc2ocnc2c1.c1ccncc1 | HO- | null | 200 | null | COc1cc(C(=O)O)ccc1-c1ccccn1.Nc1cccnc1O>>COc1cc(-c2nc3cccnc3o2)ccc1-c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0ed6a9d85f54de885301c17ac0d5c45 | COc1cc(C(=O)O)ccc1O.Nc1ccccc1O>>COc1cc(-c2nc3ccccc3o2)ccc1O | OC1=C(C=C(C(=O)O)C=C1)OC.NC1=C(C=CC=C1)O>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)O)OC | O=[C:6](O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([OH:18])[cH:16][cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1[OH:18] | COc1cc(C(=O)O)ccc1O.Nc1ccccc1O | COc1cc(-c2nc3ccccc3o2)ccc1O | null | null | C[Si](C)(C)OP(=O)=O | 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:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | 180 | CELSIUS | 8 | HOUR | 4-hydroxy-3-methoxybenzoic acid (25 g, 150 mmol) and 2-amino phenol (16 g, 150 mmol) were combined in a round bottom flask. Trimethylsilyl polyphosphate (80 mL) was added. The mixture was heated at 180° C. for 30 min. The mixture was poured over ice and allowed to stir overnight. The suspension was filtered to afford 4... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C[Si](C)(C)OP(=O)=O | 180 | 8 | COc1cc(C(=O)O)ccc1O.Nc1ccccc1O>C[Si](C)(C)OP(=O)=O>COc1cc(-c2nc3ccccc3o2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ecdd950213da4b269dd5832132410a7f | Brc1ccccn1.COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1 | COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.BrC1=NC=CC=C1>>BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | [cH:18]1[cH:19][cH:20][cH:21][c:22]([Br:23])[n:24]1.CC1(C)OB([c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)OC1(C)C>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][cH... | Brc1ccccn1.COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | OtherReaction | 36c1f2d946ae7a02459567f3196dfe6d8fcbfc8e62aa761c7cd50c306c0fdbdb | feaaf1399a28ee9a3493ca91e2c01ac85abf85c55d756e04b78cea60d3a8412c | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6])-O-C-1(-C)-C.[c:7]:[c:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[#7;a:10]:[c:11]):[c:8]:[c:7]):[c:2]:[c:3] | null | [] | 80 | CELSIUS | 24 | HOUR | 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) CsF (350 mg, 2.3 mmol), Pd(Ph3P)4 (65 mg, 0.057 mmol), and 2-bromopyridine (140 mg, 0.57 mmol) were combined in a 2-neck flask. The flask was evacuated and filled with argon and DME (5 mL) was added. The suspension w... | 10.6084/m9.figshare.5104873.v1 | null | Boronic ester | null | c1ccncc1.B1OCCO1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HO-.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 | 80 | 24 | Brc1ccccn1.COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1>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>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bcecc2c35bdc40a1afdd5bd24e47bf43 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1cccc(Br)n1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(C)n1 | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.BrC1=NC(=CC=C1)C>>COC=1C=C(C=CC1C1=NC(=CC=C1)C)C=1OC2=C(N1)C=CC=C2 | Brc1cccc(-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)n1.Br[c:18]1[cH:19][cH:20][cH:21][c:22]([CH3:23])[n:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][cH:2... | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1cccc(Br)n1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(C)n1 | null | null | null | C-C Coupling | OtherReaction | afc9eb923f86374c074e881f49ac8d91a3396ff2c46ddb13440a630e60f84eae | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].Br-c1:c:c:c:c(-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[#8:10]):[c:11]):n:1>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) was reacted with 2-bromo-6-methylpyridine (65 μL, 0.57 mmol) to afford the desired 2-[3-methox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccncc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1cccc(Br)n1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79f8843a1ec24cb78062ca26ed9f8d6e | COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1.COc1cccc(Br)n1>>COc1cccc(-c2ccc(-c3nc4ccccc4o3)cc2OC)n1 | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.BrC1=NC(=CC=C1)OC>>COC=1C=C(C=CC1C1=NC(=CC=C1)OC)C=1OC2=C(N1)C=CC=C2 | CC1(C)OB([c:8]2[cH:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]4[o:20]3)[cH:21][c:22]2[O:23][CH3:24])OC1(C)C.Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[n:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]4[o:20... | COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1.COc1cccc(Br)n1 | COc1cccc(-c2ccc(-c3nc4ccccc4o3)cc2OC)n1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 41faa5d7c8b2fa5e7977311a48e89454061b096772c8348f0e02516e76bb87f9 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].C-C1(-C)-O-B(-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[#8:10]):[c:11])-O-C-1(-C)-C>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) was reacted with 2-bromo-6-methoxypyridine (65 μL, 0.57 mmol) to afford the desired 2-[3-metho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccncc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1.c1ccc2ocnc2c1 | HBr.B | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1.COc1cccc(Br)n1>>COc1cccc(-c2ccc(-c3nc4ccccc4o3)cc2OC)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4addf6843844e34bf17ccec7031bdb4 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.O=S(=O)(Oc1ccc(Cl)cc1)C(F)(F)F>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1 | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.FC(S(=O)(=O)OC1=CC=C(C=C1)Cl)(F)F>>ClC=1C=CC(=NC1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | Br[c:23]1[cH:21][cH:20][cH:19][c:18](-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[n:24]1.O=S(=O)(Oc1ccc([Cl:22])cc1)C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:... | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.O=S(=O)(Oc1ccc(Cl)cc1)C(F)(F)F | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1 | null | null | null | Functional Group Interconversion | OtherReaction | 35ea0c0182b61297baafaac10e10b9726ae18385feb6d403fcc977632bd28a62 | d2336e76f0c6f313aff2057f08894e70849f9692cae12e374d2abc3215738e24 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.F-C(-F)(-F)-S(=O)(=O)-O-c1:c:c:c(-[Cl;H0;D1;+0:7]):c:c:1>>[Cl;H0;D1;+0:7]-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:1 | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (100 mg, 0.28 mmol) was reacted with 4-chlorophenyl trifluoromethanesulfonate (74 mg, 0.28 mmol) to afford the des... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Aromatic halide.Aromatic halide | Aromatic halide | c1ccncc1.c1ccccc1 | c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | TfOH.HBr | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.O=S(=O)(Oc1ccc(Cl)cc1)C(F)(F)F>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1cc1b4ff80e467eb9bb7babfc0aa532 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1ccc(Br)nc1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ncccc1C | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.BrC1=NC=C(C=C1)C>>COC=1C=C(C=CC1C1=NC=CC=C1C)C=1OC2=C(N1)C=CC=C2 | Brc1cccc(-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)n1.Br[c:20]1[n:19][cH:18][c:23]([CH3:24])[cH:22][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[n:19][cH:20][cH:21... | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1ccc(Br)nc1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ncccc1C | null | null | null | C-C Coupling | OtherReaction | afc9eb923f86374c074e881f49ac8d91a3396ff2c46ddb13440a630e60f84eae | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[cH;D2;+0:3]:[c:4](-[C;D1;H3:5]):[c:6]:[c:7]:1.Br-c1:c:c:c:c(-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#8:12]):[c:13]):n:1>>[#8:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:3]1:[#7;a:2]:[cH;D2;+0:1]:[c:7]:[c:6]:[c:4]:1-[C;D1;H3:5]):[c:9]:[c:10] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (150 mg, 0.43 mmol) was reacted with 2-bromo-5-methylpyridine (73 mg, 0.43 mmol) to afford the desired 2-[3-methox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccncc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1ccc(Br)nc1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ncccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f8bc0e3804441efbee05d214c16c635 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1ccnc(Br)c1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1cc(C)ccn1 | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.BrC1=NC=CC(=C1)C>>COC=1C=C(C=CC1C1=NC=CC(=C1)C)C=1OC2=C(N1)C=CC=C2 | Brc1cccc(-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)n1.Br[c:18]1[cH:19][c:20]([CH3:21])[cH:22][cH:23][n:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][c:20]([CH3:... | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1ccnc(Br)c1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cc(C)ccn1 | null | null | null | C-C Coupling | OtherReaction | afc9eb923f86374c074e881f49ac8d91a3396ff2c46ddb13440a630e60f84eae | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].Br-c1:c:c:c:c(-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[#8:10]):[c:11]):n:1>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (150 mg, 0.43 mmol) was reacted with 2-bromo-4-methylpyridine (47 μL, 0.43 mmol) to afford the desired 2-[3-methox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccncc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1ccnc(Br)c1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1cc(C)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0da76090f8245f6847f8d57e759600b | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1cccnc1Br>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(C)cn1 | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.BrC1=NC=CC=C1C>>COC=1C=C(C=CC1C1=NC=C(C=C1)C)C=1OC2=C(N1)C=CC=C2 | Brc1cccc(-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)n1.Br[c:23]1[c:21]([CH3:22])[cH:20][cH:19][cH:18][n:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][c:21... | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1cccnc1Br | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(C)cn1 | null | null | null | C-C Coupling | OtherReaction | afc9eb923f86374c074e881f49ac8d91a3396ff2c46ddb13440a630e60f84eae | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[cH;D2;+0:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7].Br-c1:c:c:c:c(-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#8:12]):[c:13]):n:1>>[#8:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:3]1:[#7;a:2]:[cH;D2;+0:1]:[c:6](-[C;D1;H3:7]):[c:5]:[c:4]:1):[c:9]:[c:10] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) was reacted with 2-bromo-3-methylpyridine (63 μL, 0.57 mmol) to afford the desired 2-[3-methox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccncc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Cc1cccnc1Br>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(C)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e63f07fedba47cdafc2bfd19692324f | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Fc1ccc(Br)cn1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(F)nc1 | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2.BrC=1C=CC(=NC1)F>>FC1=CC=C(C=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | Brc1cccc(-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)n1.Br[c:18]1[cH:19][cH:20][c:21]([F:22])[n:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][c:21](... | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Fc1ccc(Br)cn1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(F)nc1 | null | null | null | C-C Coupling | OtherReaction | afc9eb923f86374c074e881f49ac8d91a3396ff2c46ddb13440a630e60f84eae | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1cncc(-c2ccc(-c3nc4ccccc4o3)cc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.Br-c1:c:c:c:c(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[#8:11]):[c:12]):n:1>>[#8:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:8]:[c:9] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) was reacted with 5-bromo-2-fluoropyridine (59 μL, 0.57 mmol) to afford the desired 2-[4-(6-flu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccncc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr | null | null | null | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1.Fc1ccc(Br)cn1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(F)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4738a79d9195428f80343211d55d3734 | COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1.Clc1ccc(Br)cn1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)nc1 | BrC=1C=CC(=NC1)Cl.C(=O)([O-])[O-].[Na+].[Na+].BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.COC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)C=1OC2=C(N1)C=CC=C2>>ClC1=CC=C(C=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC | CC1(C)OB([c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)OC1(C)C.Br[c:18]1[cH:19][cH:20][c:21]([Cl:22])[n:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][c... | COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1.Clc1ccc(Br)cn1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)nc1 | null | null | O.COCCOC | C-C Coupling | Suzuki coupling with boronic esters | 41faa5d7c8b2fa5e7977311a48e89454061b096772c8348f0e02516e76bb87f9 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1cncc(-c2ccc(-c3nc4ccccc4o3)cc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.C-C1(-C)-O-B(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[#8:11]):[c:12])-O-C-1(-C)-C>>[#8:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:8]:[c:9] | null | [] | null | null | null | null | Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (100 mg, 0.29 mmol) was reacted with 5-bromo-2-chloropyridine (55 mg, 0.29 mmol) and Na2CO3 (90 mg, 0.86 mmol) in ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | HBr.B | O.COCCOC | null | null | COc1cc(-c2nc3ccccc3o2)ccc1B1OC(C)(C)C(C)(C)O1.Clc1ccc(Br)cn1>O.COCCOC>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ee2516367524b7eaaf9585d456e1cfd | C1COCCN1.COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(N2CCOCC2)n1 | BrC1=CC=CC(=N1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1CCOCC1.C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.CC(C)(C)[O-].[Na+]>>COC=1C=C(C=CC1C1=NC(=CC=C1)N1CCOCC1)C=1OC2=C(N1)C=CC=C2 | [NH:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1.Br[c:22]1[cH:21][cH:20][cH:19][c:18](-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[n:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1... | C1COCCN1.COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(N2CCOCC2)n1 | 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] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(-c2ccc(-c3nc4ccccc4o3)cc2)nc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | null | [] | 70 | CELSIUS | null | null | 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole (150 mg, 0.39 mmol), morpholine (41 μL, 0.47 mmol), Pd2(dba)3 (8.2 mg, 0.0078 mmol), BINAP (9.8 mg, 0.016 mmol), and NaOtBu (53 mg, 0.55 mmol) were combined in a sealable tube evacuated and backfilled with argon. Toluene (4 mL) was added and the mixture was de... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1.C1COCC[NH]1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | 70 | null | C1COCCN1.COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(Br)n1>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]>COc1cc(-c2nc3ccccc3o2)ccc1-c1cccc(N2CCOCC2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfe5da107fae4df59ca40a60daf70ae9 | C1COCCN1.COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N2CCOCC2)cn1 | ClC=1C=CC(=NC1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.N1CCOCC1.C1(=C(C=CC=C1)P(C(C)(C)C)C(C)(C)C)C1=CC=CC=C1.CC(C)(C)[O-].[Na+]>>COC=1C=C(C=CC1C1=NC=C(C=C1)N1CCOCC1)C=1OC2=C(N1)C=CC=C2 | [NH:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.Cl[c:21]1[cH:20][cH:19][c:18](-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[n:29][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1... | C1COCCN1.COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N2CCOCC2)cn1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2oc(-c3ccc(-c4ccc(N5CCOCC5)cn4)cc3)nc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]2-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-2):[c:6]:1 | null | [] | 110 | CELSIUS | null | null | 2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole (58 mg, 0.17 mmol), morpholine (18 μL, 0.21 mmol), Pd(OAc)2 (0.38 mg, 0.0017 mmol), 1,1′-biphenyl-2-yl[di(tert-butyl)]phosphine (1.0 mg, 0.0034 mmol), and NaOtBu (23 mg, 0.24 mmol) were combined in a sealable tube evacuated and backfilled with argon. Toluene ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1.C1COCC[NH]1 | HCl | CC(=O)[O-].CC(=O)[O-].[Pd+2] | 110 | null | C1COCCN1.COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1>CC(=O)[O-].CC(=O)[O-].[Pd+2]>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N2CCOCC2)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51f0adc9d41543e1b9f0d008ab664d0d | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1.N=C(c1ccccc1)c1ccccc1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N=C(c2ccccc2)c2ccccc2)cn1 | ClC=1C=CC(=NC1)C1=C(C=C(C=C1)C=1OC2=C(N1)C=CC=C2)OC.C(C1=CC=CC=C1)(C1=CC=CC=C1)=N.C1(=C(C=CC=C1)P(C1CCCCC1)C1CCCCC1)C1=CC=CC=C1.CC(C)(C)[O-].[Na+]>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2=CC=C(C=N2)N=C(C2=CC=CC=C2)C2=CC=CC=C2)OC | Cl[c:21]1[cH:20][cH:19][c:18](-[c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]3[n:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[o:14]3)[cH:15][cH:16]2)[n:37][cH:36]1.[NH:22]=[C:23]([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][c... | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1.N=C(c1ccccc1)c1ccccc1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N=C(c2ccccc2)c2ccccc2)cn1 | 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] | null | Heteroatom Alkylation and Arylation | OtherReaction | cfc71b8b6d64990fb928b26f3cf84fb88beeb8e81dfeddad763b114397ed727b | d6fdf3485f414343350878d3990b407f7838ca1f9344576c0f428d9ed6db7945 | c1ccc(C(=Nc2ccc(-c3ccc(-c4nc5ccccc5o4)cc3)nc2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH;D1;+0:7]=[C:8](-[c:9])-[c:10]>>[c:9]-[C:8](-[c:10])=[N;H0;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | 80 | CELSIUS | null | null | 2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole (100 mg, 0.30 mmol), benzophenone imine (60 μL, 0.36 mmol), Pd2(dba)3 (15 mg, 0.015 mmol), 1,1′-biphenyl-2-yl(dicyclohexyl)phosphine (10 mg, 0.015 mmol), NaOtBu (40 mg, 0.42 mmol) were combined in a sealable tube evacuated and backfilled with argon. Toluene (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted imine | Substituted imine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1.c1ccccc1.c1ccccc1 | HCl | 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] | 80 | null | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(Cl)cn1.N=C(c1ccccc1)c1ccccc1>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]>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N=C(c2ccccc2)c2ccccc2)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a752199fbaf94b028d6f53b4c6e54495 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N=C(c2ccccc2)c2ccccc2)cn1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N)cn1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2=CC=C(C=N2)N=C(C2=CC=CC=C2)C2=CC=CC=C2)OC.CC(=O)[O-].[Na+].Cl.NO>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2=CC=C(C=N2)N)OC | c1ccc(C(c2ccccc2)=[N:22][c:21]2[cH:20][cH:19][c:18](-[c:17]3[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]4[n:7][c:8]5[cH:9][cH:10][cH:11][cH:12][c:13]5[o:14]4)[cH:15][cH:16]3)[n:24][cH:23]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20]... | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N=C(c2ccccc2)c2ccccc2)cn1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N)cn1 | null | null | CO | Miscellaneous | OtherReaction | fe28e0513c54643a2e998df32fe9ad14c978580c0e1fa51268908e5a62d5d818 | 69d38cb38c5a54a23121b1c97287244fbbd5b6f97c6a1faf8cb1a05e149dd1cc | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | [c:1]:[#7;a:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:6]>>[NH2;D1;+0:5]-[c:4](:[c:6]):[c:3]:[#7;a:2]:[c:1] | null | [] | null | null | 1 | HOUR | 6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine (61 mg, 0.13 mmol) was dissolved in MeOH (2 mL) and NaOAc (25 mg, 0.31 mmol) and hydroxylamine hydrochloride (16 mg, 0.23 mmol) were added. The resulting suspension was stirred at rt for 1 h. The mixture was partitioned between CH2Cl2 and ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | Other | CO | null | 1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N=C(c2ccccc2)c2ccccc2)cn1>CO>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a63f83402bd4a00a7cdbe18b772ccfe | C=O.COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N)cn1>>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N(C)C)cn1 | O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2=CC=C(C=N2)N)OC.[BH3-]C#N.[Na+].C=O>>O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C2=CC=C(C=N2)N(C)C)OC | O=[CH2:23].[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][c:21]([NH2:22])[cH:25][n:26]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16][c:17]1-[c:18]1[cH:19][cH:20][c:21]([N:2... | C=O.COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N)cn1 | COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N(C)C)cn1 | null | CC(=O)O | CO | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | 5bc40be4d4b4346801fbfcec480fec37de3ff2eecebe2990b3686fa4792d12b6 | 5cdbf447f632627824e84e0bcac2293ea9ebd70c19b0d56dea90691653b444c7 | c1ccc(-c2ccc(-c3nc4ccccc4o3)cc2)nc1 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[C;D1;H3:8]-[N;H0;D3;+0:2](-[CH3;D1;+0:1])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | 8 | HOUR | 6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]pyridin-3-amine (22 mg, 0.070 mmol) was dissolved in MeOH (2 mL), and AcOH (2 drops). NaCNBH3 (44 mg, 0.70 mmol) and formaldehyde (50 μL, 0.70 mmol) were added and the mixture was stirred overnight. The mixture was partitioned between CH2Cl2 and dilute brine. The aqueous layer... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2ocnc2c1.c1ccncc1 | null | CC(=O)O.CO | null | 8 | C=O.COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N)cn1>CC(=O)O.CO>COc1cc(-c2nc3ccccc3o2)ccc1-c1ccc(N(C)C)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0bee724b9a494d5a960226fe611b1194 | CCOc1cc(C(=O)OC)ccc1CC#N>>COc1cc(C(=O)O)ccc1CC#N | Cl.C(#N)CC1=C(C=C(C(=O)OC)C=C1)OCC.O.[OH-].[Li+]>>C(#N)CC1=C(C=C(C(=O)O)C=C1)OC | C[CH2:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[O:8]C)[cH:9][cH:10][c:11]1[CH2:12][C:13]#[N:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[CH2:12][C:13]#[N:14] | CCOc1cc(C(=O)OC)ccc1CC#N | COc1cc(C(=O)O)ccc1CC#N | null | null | CO.C1CCOC1.O | Deprotection | OtherReaction | 55e4bf3e95c16c65d74850a39c89f1402fcf4de60571d8e32e1a486ed57af90b | e4a8940cfd45439b853de469423e6463c190060498c77b48b6eea18001b5221a | c1ccccc1 | C-[CH2;D2;+0:1]-[#8:2]-[c:3].C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]>>[CH3;D1;+0:1]-[#8:2]-[c:3].[O;D1;H0:6]=[C:5](-[OH;D1;+0:4])-[c:7] | null | [] | null | null | null | null | A solution of methyl 4-(cyanomethyl)-3-ethoxybenzoate (18 g, 88 mmol) in 150 mL of MeOH:THF:H2O (3:3:1) was treated with lithium hydroxide monohydrate (11 g, 263 mmol) at 22° C. for overnight. Then 10% aqueous HCl (100 mL) was added to quench the reaction, the mixture was extracted with EtOAc (3×200 mL), the combined o... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Ether | null | null | c1ccccc1 | Other | CO.C1CCOC1.O | null | null | CCOc1cc(C(=O)OC)ccc1CC#N>CO.C1CCOC1.O>COc1cc(C(=O)O)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a1abe5c60be4c09bf5242b5d8b1a7a5 | COc1cc(C(=O)O)ccc1CC#N.N[C@@H]1CCCC[C@H]1O>>COc1cc(C(=O)NC2CCCC[C@H]2O)ccc1CC#N | C(#N)CC1=C(C=C(C(=O)O)C=C1)OC.C(C(=O)Cl)(=O)Cl.Cl.N[C@H]1[C@@H](CCCC1)O.CN(C)C=O>>C(#N)CC1=C(C=C(C(=O)NC2[C@@H](CCCC2)O)C=C1)OC | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18]([CH2:19][C:20]#[N:21])[cH:17][cH:16]1)=[O:7].[NH2:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]2[OH:15])[cH:16][cH:17][c:18]1[CH2:19][C:20]#[N:21] | COc1cc(C(=O)O)ccc1CC#N.N[C@@H]1CCCC[C@H]1O | COc1cc(C(=O)NC2CCCC[C@H]2O)ccc1CC#N | null | null | ClCCl | 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].[C:6]-[C:7]-[C@@H;D3;+0:8](-[NH2;D1;+0:9])-[C:10](-[O;D1;H1:11])-[C:12]>>[C:6]-[C:7]-[CH;D3;+0:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10](-[O;D1;H1:11])-[C:12] | null | [] | null | null | 2 | HOUR | The 4-(cyanomethyl)-3-methoxybenzoic acid (0.33 g, 1.7 mmol) was suspended in anhydrous dichloromethane (5 mL) and treated with oxalyl chloride (0.3 mL, 3.5 mmol) followed by few drops of DMF at 22° C. under argon. After 2 h stirring, the resulting solution was concentrated to dryness, dissolved in dichloromethane (5 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCCC1 | HO- | ClCCl | null | 2 | COc1cc(C(=O)O)ccc1CC#N.N[C@@H]1CCCC[C@H]1O>ClCCl>COc1cc(C(=O)NC2CCCC[C@H]2O)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab1f6b7ec2ca44eb9d2a0d552c7197c3 | COc1cc(C(=O)NC2CCCC[C@H]2O)ccc1CC#N>>COc1cc(C(=O)NC2CCCCC2=O)ccc1CC#N | C(#N)CC1=C(C=C(C(=O)NC2[C@@H](CCCC2)O)C=C1)OC.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(#N)CC1=C(C=C(C(=O)NC2C(CCCC2)=O)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]2[OH:15])[cH:16][cH:17][c:18]1[CH2:19][C:20]#[N:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]2=[O:15])[cH:16][cH:17][c:18]1[CH2:19][C:20]#[N:21] | COc1cc(C(=O)NC2CCCC[C@H]2O)ccc1CC#N | COc1cc(C(=O)NC2CCCCC2=O)ccc1CC#N | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 53141f2efd300d3d12cff5c9fb9e873d72703f640e8dc954cbc8bc774c6bb175 | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(NC1CCCCC1=O)c1ccccc1 | [C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C@H;D3;+0:6](-[OH;D1;+0:7])-[C:8]-[C:9]>>[C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[C:9] | null | [] | 22 | CELSIUS | null | null | To a solution of oxalyl chloride (0.2 mL, 2.2 mmol) in anhydrous dichloromethane (2 mL) at −78° C. was added DMSO (0.32 mL, 4.5 mmol) under Argon. The solution was maintained for 10 min where upon a solution of 4-(cyanomethyl)-N-[(2R)-2-hydroxycyclohexyl]-3-methoxybenzamide (430 mg, 1.5 mmol) in anhydrous dichlorometha... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | null | ClCCl | 22 | null | COc1cc(C(=O)NC2CCCC[C@H]2O)ccc1CC#N>ClCCl>COc1cc(C(=O)NC2CCCCC2=O)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09ec1ce3511b4ca2a186467232961eca | COc1cc(C(=O)NC2CCCCC2=O)ccc1CC#N>>COc1cc(-c2nc3c(o2)CCCC3)ccc1CC#N | C(#N)CC1=C(C=C(C(=O)NC2C(CCCC2)=O)C=C1)OC.O=P(Cl)(Cl)Cl>>COC1=C(C=CC(=C1)C=1OC2=C(N1)CCCC2)CC#N | O=[C:9]1[CH:8]([NH:7][C:6]([c:5]2[cH:4][c:3]([O:2][CH3:1])[c:17]([CH2:18][C:19]#[N:20])[cH:16][cH:15]2)=[O:10])[CH2:14][CH2:13][CH2:12][CH2:11]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[c:9]([o:10]2)[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15][cH:16][c:17]1[CH2:18][C:19]#[N:20] | COc1cc(C(=O)NC2CCCCC2=O)ccc1CC#N | COc1cc(-c2nc3c(o2)CCCC3)ccc1CC#N | null | null | null | Aromatic Heterocycle Formation | OtherReaction | a9edcf14af481aba60ca217376654aad4e512746433ecc3aadf77d8d3773cf26 | 66ea5dd42d4e19775e64535b7106e000e9eab0f35ad97d39d6830c3addd0a08b | c1ccc(-c2nc3c(o2)CCCC3)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-[CH;D3;+0:6]-1-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:8]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:6]2:[c;H0;D3;+0:1](:[o;H0;D2;+0:9]:1)-[C:2]-[C:3]-[C:4]-[C:5]-2):[c:13]:[c:14] | null | [] | null | null | null | null | 4-(cyanomethyl)-3-methoxy-N-(2-oxocyclohexyl)benzamide (0.8 g, 2.8 mmol) was treated with POCl3 (5 mL) at reflux for 1 h. The resulting mixture was concentrated and dissolved in dichloromethane (50 mL), washed with sat. NaHCO3 (3×15 mL) and sat. brine (3×15 mL), dried (MgSO4), and concentrated in vacuo. The crude resid... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide | null | C1CCCCC1 | c1nc2c(o1)CCCC2 | c1ccccc1.c1nc2c(o1)CCCC2 | HO- | null | null | null | COc1cc(C(=O)NC2CCCCC2=O)ccc1CC#N>>COc1cc(-c2nc3c(o2)CCCC3)ccc1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d83ebcba062b4203a4c9b1278b2181ca | BrCc1ccccc1.OCCCCO>>OCCCCOCc1ccccc1 | [H-].[Na+].C(CCCO)O.C(C1=CC=CC=C1)Br.Cl>>C(C1=CC=CC=C1)OCCCCO | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | BrCc1ccccc1.OCCCCO | OCCCCOCc1ccccc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 48 | [{"value": 48.0, "product": "C(C1=CC=CC=C1)OCCCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | While a suspension containing 2.5 g of 60% sodium hydride was in 50 ml of tetrahydrofuran was allowed to stand at room temperature, 5.7 g of 1,4-butanediol was slowly added dropwise thereto. Then, a solution containing 7.5 ml of benzyl bromide in 20 ml of tetrahydrofuran was added dropwise to the reaction mixture at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | O1CCCC1 | null | 2 | BrCc1ccccc1.OCCCCO>O1CCCC1>OCCCCOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b804c6c0279240b3a7262672a29b0e17 | OCCCCOCc1ccccc1.[O-]Cl>>O=C(O)CCCOCc1ccccc1 | C(C1=CC=CC=C1)OCCCCO.Cl(=O)[O-].[Na+].Cl[O-].[Na+].P(=O)([O-])([O-])[O-].S(=O)(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>>C(C1=CC=CC=C1)OCCCC(=O)O | [CH2:2]([OH:3])[CH2:4][CH2:5][CH2:6][O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.Cl[O-:1]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | OCCCCOCc1ccccc1.[O-]Cl | O=C(O)CCCOCc1ccccc1 | null | CC1(CCCC(N1[O])(C)C)C | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 345c33ef221a703d0195f5e2e95e13b23ff84fd249db06983973a14c521bda14 | 61cf901f3ab42f325ea04925d4645e2208b580d0b1f80879b3cd6caca2ef04e0 | c1ccccc1 | Cl-[O-;H0;D1:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[O;D1;H1:5]>>[C:2]-[C:3]-[C;H0;D3;+0:4](-[O;D1;H1:5])=[O;H0;D1;+0:1] | 102 | [{"value": 102.0, "product": "C(C1=CC=CC=C1)OCCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 35 | CELSIUS | 5.5 | HOUR | 3.0 g of 4-benyloxybutanol and 182 mg of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy, radical) were dissolved in a mixture composed of 60 ml of acetonitrile and 60 ml of phosphate buffer (pH 6.7). To this reaction mixture were added 20 ml of an aqueous solution of sodium chlorite (NaClO2) (3.8 g) and 0.5 ml of a 5% aqu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | c1ccccc1 | HCl | CC1(CCCC(N1[O])(C)C)C.C(C)#N | 35 | 5.5 | OCCCCOCc1ccccc1.[O-]Cl>CC1(CCCC(N1[O])(C)C)C.C(C)#N>O=C(O)CCCOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30692bebc63d4f1ebbff40f9277d3172 | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1CCCc1ccc([N+](=O)[O-])cc1>>Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1CCCc1ccc(N)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)CCCC1=C(C(=NN1C)C1=CC=C(C=C1)F)C1=CC=NC=C1.C1=CCCCC1>>NC1=CC=C(C=C1)CCCC1=C(C(=NN1C)C1=CC=C(C=C1)F)C1=CC=NC=C1 | O=[N+:27]([O-])[c:26]1[cH:25][cH:24][c:23]([CH2:22][CH2:21][CH2:20][c:19]2[n:2]([CH3:1])[n:3][c:4](-[c:5]3[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]3)[c:12]2-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:29][cH:28]1>>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[c:12](-[c:13]2[cH:14][cH:15][n:16]... | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1CCCc1ccc([N+](=O)[O-])cc1 | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1CCCc1ccc(N)cc1 | null | [C].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCCc2[nH]nc(-c3ccccc3)c2-c2ccncc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 103 | [{"value": 103.0, "product": "NC1=CC=C(C=C1)CCCC1=C(C(=NN1C)C1=CC=C(C=C1)F)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 45 mg of 5-[3-(4-nitrophenyl)propyl]-3-(4-fluorophenyl)-1-methyl-4-(4-pyridyl)pyrazole was dissolved in 6 ml of methanol, followed by the addition of 2 ml of cyclohexene. Then, 45 mg of 10% palladium-carbon was added thereto, followed by heating under reflux for 2 hours. After the reaction mixture was filtered, the fil... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cn[nH]c1.c1ccccc1.c1ccncc1.c1ccccc1 | Other | [C].[Pd].CO | null | null | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1CCCc1ccc([N+](=O)[O-])cc1>[C].[Pd].CO>Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1CCCc1ccc(N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d4e1bbe08d4416ebf8a9bbeacc66b58 | CO.O=C(O)[C@H](O)Cc1ccccc1>>COC(=O)[C@H](O)Cc1ccccc1 | O[C@@H](C(=O)O)CC1=CC=CC=C1.S(O)(O)(=O)=O.CO>>COC([C@@H](CC1=CC=CC=C1)O)=O | [CH3:1][OH:2].O[C:3](=[O:4])[C@H:5]([OH:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([OH:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CO.O=C(O)[C@H](O)Cc1ccccc1 | COC(=O)[C@H](O)Cc1ccccc1 | null | null | C(C)OCC | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[O;D1;H1:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C:4]-[C:3](-[O;D1;H1:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6] | 85 | [{"value": 85.0, "product": "COC([C@@H](CC1=CC=CC=C1)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of (R)-2-hydroxy-3-phenylpropionic acid (1.5 g, 12.9 mol) in methanol (18 mL) at 0° C. was added concentrated sulfuric acid (0.2 mL). The reaction mixture was stirred at 0° C. for 30 min and warmed to room temperature for 24 h. Concentration in vacuo gave a residue which was diluted with diethyl ether (20... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | C(C)OCC | 0 | 0.5 | CO.O=C(O)[C@H](O)Cc1ccccc1>C(C)OCC>COC(=O)[C@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f8c307d679f4153a2cf1e3a1c6f6c09 | COC(=O)[C@H](O)Cc1ccccc1.CS(=O)(=O)Cl>>COC(=O)[C@@H](Cc1ccccc1)OS(C)(=O)=O | COC([C@@H](CC1=CC=CC=C1)O)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>COC([C@@H](CC1=CC=CC=C1)OS(=O)(=O)C)=O | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[OH:13].Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[O:13][S:14]([CH3:15])(=[O:16])=[O:17] | COC(=O)[C@H](O)Cc1ccccc1.CS(=O)(=O)Cl | COC(=O)[C@@H](Cc1ccccc1)OS(C)(=O)=O | null | null | ClCCl.C(C)OCC | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | 73 | [{"value": 73.0, "product": "COC([C@@H](CC1=CC=CC=C1)OS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "COC([C@@H](CC1=CC=CC=C1)OS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of (R)-2-hydroxy-3-phenylpropionic acid methyl ester from Step A (1.62 g, 10.9 mol) and triethylamine (3.0 mL, 21.8 mol) in dichloromethane (21.8 mL) at 0° C. was added dropwise methanesulfonyl chloride (1.28 mL, 16.4 mol). The reaction mixture was stirred at 0° C. for 1 h and was diluted with diethyl eth... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1 | HCl | ClCCl.C(C)OCC | 0 | 1 | COC(=O)[C@H](O)Cc1ccccc1.CS(=O)(=O)Cl>ClCCl.C(C)OCC>COC(=O)[C@@H](Cc1ccccc1)OS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0a31bbd9a564ae0ad27fb43af393f71 | O=[N+]([O-])c1cc(Br)cnc1O>>Nc1cc(Br)cnc1O | BrC=1C=C(C(=NC1)O)[N+](=O)[O-].O.O.[Sn](Cl)(Cl)(Cl)Cl>>NC=1C(=NC=C(C1)Br)O | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Br:5])[cH:6][n:7][c:8]1[OH:9]>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][n:7][c:8]1[OH:9] | O=[N+]([O-])c1cc(Br)cnc1O | Nc1cc(Br)cnc1O | null | null | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[O;D1;H1:5]):[#7;a:6]:[c:7]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[O;D1;H1:5]):[#7;a:6]:[c:7] | 66.7 | [{"value": 53.0, "product": "NC=1C(=NC=C(C1)Br)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "NC=1C(=NC=C(C1)Br)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 5-bromo-3-nitropyridin-2-ol (1.26 g, 4.6 mmol) and tin chloride dihydrate (3.91 g, 17.3 mmol) in ethyl acetate (19.3 mL) was heated at 50° C. for 20 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL) and washed with brine. The aqueous layer was separated and extr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | C(C)(=O)OCC | 50 | null | O=[N+]([O-])c1cc(Br)cnc1O>C(C)(=O)OCC>Nc1cc(Br)cnc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-398716f2fe394a7f9a626f6e1dd67830 | Nc1cc(Br)cnc1O.O=C(Cl)c1ccc(C(F)(F)F)cc1>>O=C(Nc1cc(Br)cnc1O)c1ccc(C(F)(F)F)cc1 | NC=1C(=NC=C(C1)Br)O.C(C)N(CC)CC.FC(C1=CC=C(C(=O)Cl)C=C1)(F)F.C([O-])([O-])=O.[K+].[K+]>>BrC=1C=C(C(=NC1)O)NC(C1=CC=C(C=C1)C(F)(F)F)=O | [NH2:3][c:4]1[cH:5][c:6]([Br:7])[cH:8][n:9][c:10]1[OH:11].Cl[C:2](=[O:1])[c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Br:7])[cH:8][n:9][c:10]1[OH:11])[c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1 | Nc1cc(Br)cnc1O.O=C(Cl)c1ccc(C(F)(F)F)cc1 | O=C(Nc1cc(Br)cnc1O)c1ccc(C(F)(F)F)cc1 | null | null | CO.C(C)(=O)OCC.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccnc1)c1ccccc1 | Cl-[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;H1:10]):[#7;a:11]:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9](-[O;D1;H1:10]):[#7;a:11]:[c:12])-[c:3](:[c:4]):[c:5] | 60 | [{"value": 60.0, "product": "BrC=1C=C(C(=NC1)O)NC(C1=CC=C(C=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "BrC=1C=C(C(=NC1)O)NC(C1=CC=C(C=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 3-amino-5-bromopyridin-2-ol from Step C (1.5 g, 7.9 mol) and triethylamine (1.64 mL, 11.9 mol) in tetrahydrofuran (15.8 mL) at 0 C was added dropwise 4-trifluoromethylbenzoyl chloride (1.2 mL, 7.9 mol). The reaction mixture was stirred at 0° C. for 1 h and warmed to room temperature for 15 h. Potassium... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | CO.C(C)(=O)OCC.O1CCCC1 | 0 | 1 | Nc1cc(Br)cnc1O.O=C(Cl)c1ccc(C(F)(F)F)cc1>CO.C(C)(=O)OCC.O1CCCC1>O=C(Nc1cc(Br)cnc1O)c1ccc(C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d20f741e39649beb44e6c36ba4af93d | COC(=O)[C@@H](Cc1ccccc1)OS(C)(=O)=O.O=C(Nc1cc(Br)cnc1O)c1ccc(C(F)(F)F)cc1>>COC(=O)[C@H](Cc1ccccc1)n1cc(Br)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O | COC([C@@H](CC1=CC=CC=C1)OS(=O)(=O)C)=O.BrC=1C=C(C(=NC1)O)NC(C1=CC=C(C=C1)C(F)(F)F)=O.[H-].[Na+]>>COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)Br)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O | CS(=O)(=O)O[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[n:13]1[cH:14][c:15]([Br:16])[cH:17][c:18]([NH:19][C:20](=[O:21])[c:22]2[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]2)[c:32]1[OH:33]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11]... | COC(=O)[C@@H](Cc1ccccc1)OS(C)(=O)=O.O=C(Nc1cc(Br)cnc1O)c1ccc(C(F)(F)F)cc1 | COC(=O)[C@H](Cc1ccccc1)n1cc(Br)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | OtherReaction | 699a843f6b8ebee9f85b24939fae6985fa9e9809eb44ac845ecad62d419a16c4 | c63aa99e5b98ee3f475502407c1e9fddf625d9a03cfead18b956dac11a6700a1 | O=C(Nc1cccn(CCc2ccccc2)c1=O)c1ccccc1 | C-S(=O)(=O)-O-[C@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].[O;D1;H0:8]=[C:9]-[#7:10]-[c:11]1:[c:12]:[c:13]:[c:14]:[n;H0;D2;+0:15]:[c;H0;D3;+0:16]:1-[OH;D1;+0:17]>>[C;D1;H3:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C@H;D3;+0:1](-[C:2]-[c:3])-[n;H0;D3;+0:15]1:[c:14]:[c:13]:[c:12]:[c:11](-[#7:10]-[C:9]=[O;D1;H0... | 70.1 | [{"value": 70.0, "product": "COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)Br)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)Br)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of N-(5-bromo-2-hydroxypyridin-3-yl)-4-trifluoromethyl-benzamide from Step D (760 mg, 2.1 mmol) in tetrahydrofuran (10 mL) was added 95% sodium hydride (80 mg, 3.15 mmol) at room temperature. After the reaction mixture was stirred at room temperature for 30 min, (R)-2-methanesulfonyloxy-3-phenylpropionic ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Ester.Aromatic alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | MsOH.HO- | C(C)(=O)OCC.O1CCCC1 | null | 0.5 | COC(=O)[C@@H](Cc1ccccc1)OS(C)(=O)=O.O=C(Nc1cc(Br)cnc1O)c1ccc(C(F)(F)F)cc1>C(C)(=O)OCC.O1CCCC1>COC(=O)[C@H](Cc1ccccc1)n1cc(Br)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a77d0470a194567bea60da99ff1e7cf | COC(=O)[C@H](Cc1ccccc1)n1cc(Br)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O.OB(O)c1cccc2ccccc12>>COC(=O)[C@H](Cc1ccccc1)n1cc(-c2cccc3ccccc23)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O | COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)Br)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O.B(C1=CC=CC2=CC=CC=C12)(O)O.[F-].[Cs+]>>COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)C1=CC=CC2=CC=CC=C12)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O | Br[c:15]1[cH:14][n:13]([C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:41](=[O:42])[c:27]([NH:28][C:29](=[O:30])[c:31]2[cH:32][cH:33][c:34]([C:35]([F:36])([F:37])[F:38])[cH:39][cH:40]2)[cH:26]1.OB(O)[c:16]1[cH:17][cH:18][cH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12>>[CH3:1][O:2... | COC(=O)[C@H](Cc1ccccc1)n1cc(Br)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O.OB(O)c1cccc2ccccc12 | COC(=O)[C@H](Cc1ccccc1)n1cc(-c2cccc3ccccc23)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O | null | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C | O1CCCC1.C(C)OCC | C-C Coupling | Suzuki coupling with boronic acids | cc7b6546c43ae6dc4b9bf5c56c03385a5aaa3d7e8a3c63cb3d09ccb8ae48e364 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(Nc1cc(-c2cccc3ccccc23)cn(CCc2ccccc2)c1=O)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]):[c:8]:[c:9]:[c:10]:1.O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](:[c:15]):[c:16]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](:[c:15]):[c:16]):[c:10]:[c:9]:[c:8]:1 | 81 | [{"value": 81.0, "product": "COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)C1=CC=CC2=CC=CC=C12)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)C1=CC=CC2=CC=CC=C12)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O", "details": "CALCULATEDPERCEN... | null | null | null | null | A mixture of (S)-2-[5-bromo-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester from Step E (66.8 mg, 0.128 mmol), 1-naphthyleneboronic acid (44.0 mg, 0.256 mmol), cesium fluoride (97 mg, 0.64 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform complex (13.0 mg, 0.013 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccc2ccccc2c1 | c1ccncc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccncc1.c1ccc2ccccc2c1.c1ccccc1 | HBr.B | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O1CCCC1.C(C)OCC | null | null | COC(=O)[C@H](Cc1ccccc1)n1cc(Br)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O.OB(O)c1cccc2ccccc12>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O1CCCC1.C(C)OCC>COC(=O)[C@H](Cc1ccccc1)n1cc(-c2cccc3ccccc23)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bc70584fccd43939cccf6094ec7e59c | COC(=O)[C@H](Cc1ccccc1)n1cc(-c2cccc3ccccc23)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O>>O=C(Nc1cc(-c2cccc3ccccc23)cn([C@@H](Cc2ccccc2)C(=O)O)c1=O)c1ccc(C(F)(F)F)cc1 | COC([C@H](CC1=CC=CC=C1)N1C(C(=CC(=C1)C1=CC=CC2=CC=CC=C12)NC(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O.[OH-].[Li+].Cl>>C1(=CC=CC2=CC=CC=C12)C=1C=C(C(N(C1)[C@H](C(=O)O)CC1=CC=CC=C1)=O)NC(C1=CC=C(C=C1)C(F)(F)F)=O | C[O:29][C:27]([C@@H:19]([n:18]1[cH:17][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[cH:5][c:4]([NH:3][C:2](=[O:1])[c:32]2[cH:33][cH:34][c:35]([C:36]([F:37])([F:38])[F:39])[cH:40][cH:41]2)[c:30]1=[O:31])[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)=[O:28]>>[O:1]=[C:2]([NH:3][c:4]1[c... | COC(=O)[C@H](Cc1ccccc1)n1cc(-c2cccc3ccccc23)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O | O=C(Nc1cc(-c2cccc3ccccc23)cn([C@@H](Cc2ccccc2)C(=O)O)c1=O)c1ccc(C(F)(F)F)cc1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1cc(-c2cccc3ccccc23)cn(CCc2ccccc2)c1=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | A mixture of (S)-2-[5-naphthalen-1-yl-2-oxo-3-(4-trifluoromethyl-benzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester from Step F (31 mg, 0.054 mmol) and 1N lithium hydroxide (2.0 mL) in tetrahydrofuran (2.0 mL) was stirred at room temperature for 1 h. 1N Hydrochloric acid (3 mL) was added and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccc2ccccc2c1.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | 1 | COC(=O)[C@H](Cc1ccccc1)n1cc(-c2cccc3ccccc23)cc(NC(=O)c2ccc(C(F)(F)F)cc2)c1=O>O1CCCC1>O=C(Nc1cc(-c2cccc3ccccc23)cn([C@@H](Cc2ccccc2)C(=O)O)c1=O)c1ccc(C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98aa98faae864ca0bb31f6d0d7981447 | CCN(CC)CCCNC(N)=S.O=C(CCl)C1(c2ccc(Cl)cc2)CCC1>>CCN(CC)CCCNc1nc(C2(c3ccc(Cl)cc3)CCC2)cs1 | ClCC(=O)C1(CCC1)C1=CC=C(C=C1)Cl.[I-].[Na+].C(C)N(CCCNC(=S)N)CC>>ClC1=CC=C(C=C1)C1(CCC1)C=1N=C(SC1)NCCCN(CC)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH2:11])=[S:25].O=[C:12]([C:13]1([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22][CH2:23]1)[CH2:24]Cl>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][c:10]1[n:11][c:12]([C:13]2([c:14]3[cH:15][cH:16][c:17]([Cl:18])[... | CCN(CC)CCCNC(N)=S.O=C(CCl)C1(c2ccc(Cl)cc2)CCC1 | CCN(CC)CCCNc1nc(C2(c3ccc(Cl)cc3)CCC2)cs1 | null | null | CC(=O)C.O.C(O)([O-])=O.[Na+] | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(C2(c3cscn3)CCC2)cc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](-[c:4])(-[C:5])-[C:6].[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11]>>[C:5]-[C:3](-[c:4])(-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[s;H0;D2;+0:11]:[c;H0;D3;+0:9](-[#7:8]-[C:7]):[n;H0;D2;+0:10]:1)-[C:6] | 86.8 | [{"value": 86.8, "product": "ClC1=CC=C(C=C1)C1(CCC1)C=1N=C(SC1)NCCCN(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A solution of 2-chloro-1-[1-(4-chlorophenyl)cyclobutyl]ethanone (120 mg, 0.494 mmol) and sodium iodide (74 mg, 0.494 mmol) in acetone (2.5 mL) was stirred at room temperature for 5 minutes. Next (3-diethylaminopropyl)thiourea (94 mg, 0.494 mmol) was added. The resulting mixture was heated at 50° C. for 1 h. After the m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1cscn1.c1ccccc1.C1CCC1 | HCl | CC(=O)C.O.C(O)([O-])=O.[Na+] | 50 | null | CCN(CC)CCCNC(N)=S.O=C(CCl)C1(c2ccc(Cl)cc2)CCC1>CC(=O)C.O.C(O)([O-])=O.[Na+]>CCN(CC)CCCNc1nc(C2(c3ccc(Cl)cc3)CCC2)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7df2cf2c036f4ca89fda9641812f2c45 | O=C(O)CC(O)(CC(=O)O)C(=O)O>>O=C(O)CC(O)(CC(=O)O)C(=O)O | ClC1=CC=C(C=C1)C1(CCC1)C=1N=C(SC1)NCCCN(CC)CC.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>C(CC(O)(C(=O)O)CC(=O)O)(=O)O.ClC1=CC=C(C=C1)C1(CCC1)C=1N=C(SC1)NCCCN(CC)CC | [O:26]=[C:27]([OH:28])[CH2:29][C:30]([OH:31])([CH2:32][C:33](=[O:34])[OH:35])[C:36](=[O:37])[OH:38]>>[O:26]=[C:27]([OH:28])[CH2:29][C:30]([OH:31])([CH2:32][C:33](=[O:34])[OH:35])[C:36](=[O:37])[OH:38] | O=C(O)CC(O)(CC(=O)O)C(=O)O | O=C(O)CC(O)(CC(=O)O)C(=O)O | null | null | CO.O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | A solution of N′-{4-[1-(4-chlorophenyl)cyclobutyl]thiazol-2-yl}-N,N-diethylpropane-1,3-diamine, 19, (78.9 mg, 0.209 mmol) and citric acid (40.2 mg, 0.209 mmol) in methanol (10 mL) was concentrated to give a colorless oil. The oil was dissolved in water (10 mL) and lyophilized to give N′-{4-[1-(4-chlorophenyl)cyclobutyl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO.O | null | null | O=C(O)CC(O)(CC(=O)O)C(=O)O>CO.O>O=C(O)CC(O)(CC(=O)O)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e8b147a67fa40c69b7aff3d49bc0289 | CN1CCCC1CCN.S=C=S>>CN1CCCC1CCN=C=S | C(O)([O-])=O.[Na+].NCCC1N(CCC1)C.C(=S)=S.ClC(=O)OCC>>N(=C=S)CCC1N(CCC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH2:9].S=[C:10]=[S:11]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]=[C:10]=[S:11] | CN1CCCC1CCN.S=C=S | CN1CCCC1CCN=C=S | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 99faaca01b29bb4aacdf8b5dd838744c8a4a0ba5e793c41d71f6ab61fd987eaa | b4d1d5962cf9cde357eea1a492f332beb32c18a22c0b29a341204737bdcfdaa7 | C1CCNC1 | S=[C;H0;D2;+0:1]=[S;D1;H0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[N;H0;D2;+0:5]=[C;H0;D2;+0:1]=[S;D1;H0:2] | 43.2 | [{"value": 43.2, "product": "N(=C=S)CCC1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A mixture of carbon disulfide (0.996 mL, 16.57 mmol) in water (5 mL) was cooled to 0° C. Then 2-(2-aminoethyl)-1-methylpyrrolidine (2.4 mL, 16.57 mmol) was added over 45 minutes. The resulting mixture was maintained at 0° C. for an additional 30 minutes and then the cooling was discontinued. Next, ethyl chloroformate (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Isothiocyanate | null | null | C1CC[NH]C1 | Other | O | 0 | null | CN1CCCC1CCN.S=C=S>O>CN1CCCC1CCN=C=S |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c3f3afcea9a427b9b1ed5038ccd9a33 | CN1CCCC1CCN=C=S.[NH4+]>>CN1CCCC1CCNC(N)=S | N(=C=S)CCC1N(CCC1)C.[OH-].[NH4+].[OH-].[NH4+]>>CN1C(CCC1)CCNC(=S)N | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]=[C:10]=[S:12].[NH4+:11]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][C:10]([NH2:11])=[S:12] | CN1CCCC1CCN=C=S.[NH4+] | CN1CCCC1CCNC(N)=S | null | null | null | Functional Group Addition | OtherReaction | cd4f83699195920526e72e493431bc8976f3c401602e991b6e86d9e6dbeb75ce | 511e88f11fcb676c82352eecef8a557fb89a4e4c71a3ad25e2178673f2085e3e | C1CCNC1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[NH4+;D0:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:6])=[S;D1;H0:5] | null | [] | null | null | 30 | MINUTE | The 2-(2-isothiocyanatoethyl)-1-methylpyrrolidine and concentrated ammonium hydroxide (3 mL) were heated at 100° C. for 30 minutes. Additional ammonium hydroxide (1 mL) was added and heating was continued for an additional 30 minutes. The reaction mixture was allowed to cool to room temperature and then it was lyophili... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Thiourea | null | null | C1CC[NH]C1 | null | null | null | 0.5 | CN1CCCC1CCN=C=S.[NH4+]>>CN1CCCC1CCNC(N)=S |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fd4221a2141460394cd5eff727d42ea | BrCCCBr.N#CCc1ccc(Cl)cc1>>N#CC1(c2ccc(Cl)cc2)CCC1 | ClC1=CC=C(C=C1)CC#N.BrCCCBr.CS(=O)C.[H-].[Na+]>>ClC1=CC=C(C=C1)C1(CCC1)C#N | Br[CH2:11][CH2:12][CH2:13]Br.[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]2)[CH2:11][CH2:12][CH2:13]1 | BrCCCBr.N#CCc1ccc(Cl)cc1 | N#CC1(c2ccc(Cl)cc2)CCC1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | e40fe0b024bba888bda6ca819b5ab269bd5a04ef5dd7ee26f30868d617c569e8 | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | c1ccc(C2CCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-Br.[N;D1;H0:4]#[C:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[N;D1;H0:4]#[C:5]-[C;H0;D4;+0:6]1(-[c:7](:[c:8]):[c:9])-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-1 | 68.2 | [{"value": 68.2, "product": "ClC1=CC=C(C=C1)C1(CCC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a round-bottom flask under argon fitted with an addition funnel and thermometer was added anhydrous dimethylsulfoxide and sodium hydride (1.17 g, 48.8 mmol, 95%). Then a solution of (4-chlorophenyl)acetonitrile (A) (2.70 mL, 22.2 mmol) and 1,3-dibromopropane (2.48 mL, 24.4 mmol) in diethyl ether (15 mL) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CCC1 | c1ccccc1.C1CCC1 | HBr | C(C)OCC | null | null | BrCCCBr.N#CCc1ccc(Cl)cc1>C(C)OCC>N#CC1(c2ccc(Cl)cc2)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f8f6d6c43c6541ceab51d40476341898 | BrCCOCCBr.N#CCc1ccc(Cl)cc1>>N#CC1(c2ccc(Cl)cc2)CCOCC1 | ClC1=CC=C(C=C1)CC#N.BrCCOCCBr.CS(=O)C.[H-].[Na+]>>ClC1=CC=C(C=C1)C1(CCOCC1)C#N | Br[CH2:11][CH2:12][O:13][CH2:14][CH2:15]Br.[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1 | BrCCOCCBr.N#CCc1ccc(Cl)cc1 | N#CC1(c2ccc(Cl)cc2)CCOCC1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 7a02bf4931a2667c7a560f7e10856bd80597aeb566d8b87c38850fad3f2124c8 | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | c1ccc(C2CCOCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.[N;D1;H0:6]#[C:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:6]#[C:7]-[C;H0;D4;+0:8]1(-[c:9](:[c:10]):[c:11])-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1 | 95.5 | [{"value": 95.5, "product": "ClC1=CC=C(C=C1)C1(CCOCC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a round-bottom flask under argon fitted with an addition funnel and thermometer was added anhydrous dimethylsulfoxide (60 mL) and sodium hydride (1.17 g, 48.8 mmol, 95%). Then a solution of (4-chlorophenyl)acetonitrile (G) (3.37 g, 22.2 mmol) and 2-bromoethyl ether (90%, 3.41 mL, 24.4 mmol) in diethyl ether (15 mL... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CCOCC1 | c1ccccc1.C1CCOCC1 | HBr | C(C)OCC | null | null | BrCCOCCBr.N#CCc1ccc(Cl)cc1>C(C)OCC>N#CC1(c2ccc(Cl)cc2)CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e50920a65c84cceb267c0eb5f5e0bcb | NC(=S)NCCCN1CCOCC1.O=C(CCl)C1(c2ccc(Cl)cc2)CCCCC1>>Clc1ccc(C2(c3csc(NCCCN4CCOCC4)n3)CCCCC2)cc1 | ClCC(=O)C1(CCCCC1)C1=CC=C(C=C1)Cl.[I-].[Na+].O1CCN(CC1)CCCNC(=S)N>>ClC1=CC=C(C=C1)C1(CCCCC1)C=1N=C(SC1)NCCCN1CCOCC1 | [S:9]=[C:10]([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[NH2:21].O=[C:7]([C:6]1([c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:28][cH:27]2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[CH2:8]Cl>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([C:6]2([c:7]3[cH:8][s:9][c:10]([NH:11][CH2:12][CH2:13][CH2:14][N:15]4[CH2:1... | NC(=S)NCCCN1CCOCC1.O=C(CCl)C1(c2ccc(Cl)cc2)CCCCC1 | Clc1ccc(C2(c3csc(NCCCN4CCOCC4)n3)CCCCC2)cc1 | null | null | CC(=O)C.O.C(O)([O-])=O.[Na+] | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(C2(c3csc(NCCCN4CCOCC4)n3)CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](-[c:4])(-[C:5])-[C:6].[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11]>>[C:7]-[#7:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:2](-[C:3](-[c:4])(-[C:5])-[C:6]):[cH;D2;+0:1]:[s;H0;D2;+0:11]:1 | null | [] | 50 | CELSIUS | null | null | A solution of 2-chloro-1-[1-(4-chloro-phenyl)-cyclohexyl]-ethanone (191.5 mg, 0.71 mmol) and sodium iodide (105.8 mg, 0.71 mmol) in acetone (5 mL) was stirred at room temperature for 10 min. Next, 1-(3-morpholinopropyl)-2-thiourea (143.6 mg, 0.71 mmol) was added. The resulting mixture was heated at 50° C. overnight. Af... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1ccccc1.c1cscn1.C1COCC[NH]1.C1CCCCC1 | HCl | CC(=O)C.O.C(O)([O-])=O.[Na+] | 50 | null | NC(=S)NCCCN1CCOCC1.O=C(CCl)C1(c2ccc(Cl)cc2)CCCCC1>CC(=O)C.O.C(O)([O-])=O.[Na+]>Clc1ccc(C2(c3csc(NCCCN4CCOCC4)n3)CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6a60bac2edd4b239c9aa92fbc731b55 | CN1CCCC1CCNC(N)=S.O=C(CCl)C1(c2ccc(Cl)cc2)CCCCC1>>CN1CCCC1CCNc1nc(C2(c3ccc(Cl)cc3)CCCCC2)cs1 | ClCC(=O)C1(CCCCC1)C1=CC=C(C=C1)Cl.[I-].[Na+].CN1C(CCC1)CCNC(=S)N>>ClC1=CC=C(C=C1)C1(CCCCC1)C=1N=C(SC1)NCCC1N(CCC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][C:10]([NH2:11])=[S:27].O=[C:12]([C:13]1([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:26]Cl>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][c:10]1[n:11][c:12]([C:13]2([c:14]3[cH:15][cH:16][c... | CN1CCCC1CCNC(N)=S.O=C(CCl)C1(c2ccc(Cl)cc2)CCCCC1 | CN1CCCC1CCNc1nc(C2(c3ccc(Cl)cc3)CCCCC2)cs1 | null | null | CC(=O)C.O.C(O)([O-])=O.[Na+] | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(C2(c3csc(NCCC4CCCN4)n3)CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](-[c:4])(-[C:5])-[C:6].[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11]>>[C:5]-[C:3](-[c:4])(-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[s;H0;D2;+0:11]:[c;H0;D3;+0:9](-[#7:8]-[C:7]):[n;H0;D2;+0:10]:1)-[C:6] | null | [] | 50 | CELSIUS | null | null | A solution of 2-chloro-1-[1-(4-chloro-phenyl)-cyclohexyl]-ethanone (144.8 mg, 0.53 mmol) and sodium iodide (80 mg, 0.53 mmol) in acetone (4 mL) was stirred at room temperature for 10 min. Next, [2-(1-methyl-pyrrolidin-yl)ethyl] thiourea (100 mg, 0.71 mmol) was added. The resulting mixture was heated at 50° C. overnight... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | C1CC[NH]C1.c1cscn1.c1ccccc1.C1CCCCC1 | HCl | CC(=O)C.O.C(O)([O-])=O.[Na+] | 50 | null | CN1CCCC1CCNC(N)=S.O=C(CCl)C1(c2ccc(Cl)cc2)CCCCC1>CC(=O)C.O.C(O)([O-])=O.[Na+]>CN1CCCC1CCNc1nc(C2(c3ccc(Cl)cc3)CCCCC2)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fdc316a0291b42b1a7dd67566c32369f | CN(C(=O)OC(C)(C)C)C1CCNC1.S=C(n1ccnc1)n1ccnc1>>CN(C(=O)OC(C)(C)C)C1CCN(C(N)=S)C1 | C(=S)(N1C=NC=C1)N1C=NC=C1.C(C)(C)(C)OC(N(C1CNCC1)C)=O>>C(C)(C)(C)OC(N(C1CN(CC1)C(N)=S)C)=O | [CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]1[CH2:11][CH2:12][NH:13][CH2:17]1.c1cn([C:14]([n:15]2ccnc2)=[S:16])cn1>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]1[CH2:11][CH2:12][N:13]([C:14]([NH2:15])=[S:16])[CH2:17]1 | CN(C(=O)OC(C)(C)C)C1CCNC1.S=C(n1ccnc1)n1ccnc1 | CN(C(=O)OC(C)(C)C)C1CCN(C(N)=S)C1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 06c21d6dff90ae4756cc040cc5b3f7050bcb57b0889bac3068ec6ce5876c0de5 | 377f627d6f4dccba0e2f73a30b05ceaf32e1dcc3d8eef8e3528c5eb6591d375d | C1CCNC1 | [C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-1.[S;D1;H0:6]=[C;H0;D3;+0:7](-[n;H0;D3;+0:8]1:c:c:n:c:1)-n1:c:c:n:c:1>>[NH2;D1;+0:8]-[C;H0;D3;+0:7](=[S;D1;H0:6])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[C:1]-[C:5]-1 | 64.9 | [{"value": 64.9, "product": "C(C)(C)(C)OC(N(C1CN(CC1)C(N)=S)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.2, "product": "C(C)(C)(C)OC(N(C1CN(CC1)C(N)=S)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirring solution of thiocarbonyldiimidazole (1.23 g, 6.91 mmol) in THF (10 mL) under N2 was added methylpyrrolidin-3-yl-carbamic acid tert-butyl ester (1.20 g, 5.99 mmol) in THF (7 mL). The reaction mixture was stirred at room temperature of 1 h, and then at 55° C. for 2 h. The reaction was cooled to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Thiocarbonyl | Thiourea | C1CCNC1.c1c[nH]cn1.c1c[nH]cn1 | C1CC[NH]C1 | C1CC[NH]C1 | Other | C1CCOC1 | null | 1 | CN(C(=O)OC(C)(C)C)C1CCNC1.S=C(n1ccnc1)n1ccnc1>C1CCOC1>CN(C(=O)OC(C)(C)C)C1CCN(C(N)=S)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-793139195a0c4d8191a85ccb7a10382e | CN(C)C1CCNC1.N#C[S-]>>CN(C)C1CCN(C(N)=S)C1 | [S-]C#N.[K+].[Cl-].CN(C1CNCC1)C>>CN(C1CN(CC1)C(N)=S)C | [CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][NH:7][CH2:11]1.[C:8](#[N:9])[S-:10]>>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][N:7]([C:8]([NH2:9])=[S:10])[CH2:11]1 | CN(C)C1CCNC1.N#C[S-] | CN(C)C1CCN(C(N)=S)C1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d0d9f15ef0cb533cd5bae9a50f95d1986122faf935914870b3400e021f1b2b6e | 762a47d886662ff1ef990b9f896ce0a1a4778103bf6616b3961d53c7efb7da4c | C1CCNC1 | [C:1]1-[C:2]-[C:3]-[C:4]-[NH;D2;+0:5]-1.[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[S-;H0;D1:8]>>[NH2;D1;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[N;H0;D3;+0:5]1-[C:1]-[C:2]-[C:3]-[C:4]-1 | 23.9 | [{"value": 23.3, "product": "CN(C1CN(CC1)C(N)=S)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.9, "product": "CN(C1CN(CC1)C(N)=S)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | To a suspension of potassium thiocyanate (2.02 g, 20.8 mmol) in acetone (10.7 mL) at 0° C. was slowly added pivolyl chloride (2.6 mL, 21.1 mmol). The mixture was stirred at 0° C. for 3 h. Dimethylpyrrolidin-3-yl-amine (2.44 g, 21.3 mmol) was added slowly at 0° C., and the reaction was allowed to warm to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary amine | Thiourea | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | null | CC(=O)C | 0 | 3 | CN(C)C1CCNC1.N#C[S-]>CC(=O)C>CN(C)C1CCN(C(N)=S)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2f702acf9204650b931ca10badf77fa | C=CC(C)=O.COc1ccc2c(c1)CC(C)C2=O>>COc1ccc2c(c1)CC(C)(CCC(C)=O)C2=O | COC=1C=C2CC(C(C2=CC1)=O)C.N12CCCCCC2=NCCC1.C(=C)C(=O)C>>COC=1C=C2CC(C(C2=CC1)=O)(CCC(C)=O)C | [CH2:12]=[CH:13][C:14]([CH3:15])=[O:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH:10]([CH3:11])[C:17]2=[O:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][C:14]([CH3:15])=[O:16])[C:17]2=[O:18] | C=CC(C)=O.COc1ccc2c(c1)CC(C)C2=O | COc1ccc2c(c1)CC(C)(CCC(C)=O)C2=O | null | null | CCOC(=O)C.O1CCCC1 | C-C Coupling | OtherReaction | c504c0d32586144b6874498db3cc99d4d5bb675e1b2e725385a0386d3f14ac05 | 68a0b2d4768a64505cf15a6dd6bbd75216aef3c50fb86aff9b39341b3e49f06d | O=C1CCc2ccccc21 | [C;D1;H3:1]-[CH;D3;+0:2]1-[C:3]-[c:4]:[c:5]-[C:6]-1=[O;D1;H0:7].[C;D1;H3:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[C;D1;H3:1]-[C;H0;D4;+0:2]1(-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[C:9](-[C;D1;H3:8])=[O;D1;H0:10])-[C:3]-[c:4]:[c:5]-[C:6]-1=[O;D1;H0:7] | 332.6 | [{"value": 332.6, "product": "COC=1C=C2CC(C(C2=CC1)=O)(CCC(C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 5-methoxy-2-methyl-1-indanone (0.5 g, 2.84 mmol) in anhydrous tetrahydrofuran (3 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (0.085 mL, 0.57 mmol) and methyl vinyl ketone (0.473 mL, 5.68 mmol). The resulting solution was placed under a nitrogen atmosphere and stirred at room temperature overni... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | CCOC(=O)C.O1CCCC1 | null | 8 | C=CC(C)=O.COc1ccc2c(c1)CC(C)C2=O>CCOC(=O)C.O1CCCC1>COc1ccc2c(c1)CC(C)(CCC(C)=O)C2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6636cf7073446fb80a814617775f2cf | COc1ccc2c(c1)CC(C)(CCC(C)=O)C2=O>>COc1ccc2c(c1)CC1(C)CCC(=O)C=C21 | N1CCCC1.C(C)(=O)O.COC=1C=C2CC(C(C2=CC1)=O)(CCC(C)=O)C>>COC1=CC=C2C3=CC(CCC3(CC2=C1)C)=O | O=[C:17]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][C:10]1([CH3:11])[CH2:12][CH2:13][C:14](=[O:15])[CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH3:11])[CH2:12][CH2:13][C:14](=[O:15])[CH:16]=[C:17]21 | COc1ccc2c(c1)CC(C)(CCC(C)=O)C2=O | COc1ccc2c(c1)CC1(C)CCC(=O)C=C21 | null | null | CCOC(=O)C.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C;D1;H3:7])-[C:8]-[C:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C;D1;H3:7]-[C:6]12-[C:8]-[C:9]-[C:10](=[O;D1;H0:12])-[CH;D2;+0:11]=[C;H0;D3;+0:1]-1-[c:2](:[c:3]):[c:4]-[C:5]-2 | 99.1 | [{"value": 99.1, "product": "COC1=CC=C2C3=CC(CCC3(CC2=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Pyrrolidine (0.159 mL, 1.9 mmol) and acetic acid (0.109 mL, 1.9 mmol) were added to a solution of 5-methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone (467 mg, 1.9 mmol) in toluene (5 mL) and the resulting solution was heated in an oil bath at 85° C. for 2.5 hours. After cooling to room temperature, the reaction mixture was d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | CCOC(=O)C.C1(=CC=CC=C1)C | 85 | null | COc1ccc2c(c1)CC(C)(CCC(C)=O)C2=O>CCOC(=O)C.C1(=CC=CC=C1)C>COc1ccc2c(c1)CC1(C)CCC(=O)C=C21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca78e012a7fe470cbc127bc7a9674487 | BrBr.COc1ccc2c(c1)CC1(C)CCC(=O)C=C21>>COc1ccc2c(c1)CC1(C)CCC(=O)C(Br)=C21 | COC1=CC=C2C3=CC(CCC3(CC2=C1)C)=O.C(=O)(O)[O-].[Na+].BrBr>>BrC=1C(CCC2(CC3=CC(=CC=C3C12)OC)C)=O | Br[Br:17].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH3:11])[CH2:12][CH2:13][C:14](=[O:15])[CH:16]=[C:18]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH3:11])[CH2:12][CH2:13][C:14](=[O:15])[C:16]([Br:17])=[C:18]21 | BrBr.COc1ccc2c(c1)CC1(C)CCC(=O)C=C21 | COc1ccc2c(c1)CC1(C)CCC(=O)C(Br)=C21 | null | null | CCOC(=O)C.C(Cl)Cl | Functional Group Interconversion | Bromination | 73ca391a48874f0a81f3694c6623ffb0a512c874931d8f551485082fa4a0d563 | c7222534d68e666d405fc6d911092ac63e3791780d01400eb414eff6e46c2a54 | O=C1C=C2c3ccccc3CC2CC1 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3](=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[C:7])-[c:8]>>[Br;H0;D1;+0:1]-[C;H0;D3;+0:4](=[C:3](-[C:2])-[c:8])-[C:5](=[O;D1;H0:6])-[C:7] | 46.5 | [{"value": 46.5, "product": "BrC=1C(CCC2(CC3=CC(=CC=C3C12)OC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | A mixture of 7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (32 mg, 0.14 mmol) and NaHCO3 (60 mg, 0.7 mmol) in CH2Cl2 (0.5 ml) was treated with bromine (0.008 mL, 0.154 mmol), and the resulting mixture was stirred at room temperature for 22 hours. The mixture was diluted with EtOAc (8 ml), washed with dilute ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HBr | CCOC(=O)C.C(Cl)Cl | null | 22 | BrBr.COc1ccc2c(c1)CC1(C)CCC(=O)C=C21>CCOC(=O)C.C(Cl)Cl>COc1ccc2c(c1)CC1(C)CCC(=O)C(Br)=C21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e5a1851da29e4f9a858bacb45e92bc64 | COc1ccc2c(c1)CC1(C)CCC(=O)C(Br)=C21>>CC12CCC(=O)C(Br)=C1c1ccc(O)cc1C2 | B(Br)(Br)Br.C(Cl)Cl.BrC=1C(CCC2(CC3=CC(=CC=C3C12)OC)C)=O>>BrC=1C(CCC2(CC3=CC(=CC=C3C12)O)C)=O | C[O:14][c:13]1[cH:12][cH:11][c:10]2[c:16]([cH:15]1)[CH2:17][C:2]1([CH3:1])[CH2:3][CH2:4][C:5](=[O:6])[C:7]([Br:8])=[C:9]12>>[CH3:1][C:2]12[CH2:3][CH2:4][C:5](=[O:6])[C:7]([Br:8])=[C:9]1[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]1[CH2:17]2 | COc1ccc2c(c1)CC1(C)CCC(=O)C(Br)=C21 | CC12CCC(=O)C(Br)=C1c1ccc(O)cc1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | 1M BBr3 in CH2Cl2 (0.200 mL, 0.2 mmol) was added to an ice-cold solution of 4-bromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (10 mg, 0.033 mmol) in CH2CL2 (0.5 mL). The cooling bath was removed and the solution was stirred at room temperature for 30 minutes, then treated with more BBr3 in CH2CL2 (0.5 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | null | null | 0.5 | COc1ccc2c(c1)CC1(C)CCC(=O)C(Br)=C21>>CC12CCC(=O)C(Br)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92a03a8e4c1e41349e525d8248b38466 | CCCC=O.COc1ccc2c(c1)CCC2=O>>CCCCC1Cc2cc(OC)ccc2C1=O | [OH-].[K+].COC=1C=C2CCC(C2=CC1)=O.C(CCC)=O>>C(CCC)C1C(C2=CC=C(C=C2C1)OC)=O | O=[CH:4][CH2:3][CH2:2][CH3:1].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[C:15]1=[O:16] | CCCC=O.COc1ccc2c(c1)CCC2=O | CCCCC1Cc2cc(OC)ccc2C1=O | null | [Pd] | C(C)O | C-C Coupling | OtherReaction | 68e28f9095e1f150f32da6921211b9a27c818a0dd75d077bb5baa7c9b256c798 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1CCc2ccccc21 | O=[CH;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[CH2;D2;+0:6]-[C:7]-[c:8]:[c:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:6]1-[C:7]-[c:8]:[c:9]-[C:5]-1=[O;D1;H0:4] | 104.1 | [{"value": 104.1, "product": "C(CCC)C1C(C2=CC=C(C=C2C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Potassium hydroxide (0.44 g, 85% weight pure, 6.67 mmol) and 10% palladium on activated carbon (0.42 g) were added to a mixture of 5-methoxy-1-indanone (5.0 g, 30.8 mmol) and butyraldehyde (3.3 mL, 37 mmol) in ethanol (30 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature for 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | [Pd].C(C)O | null | 2 | CCCC=O.COc1ccc2c(c1)CCC2=O>[Pd].C(C)O>CCCCC1Cc2cc(OC)ccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a68e6a4e18124f449bac70683f3eb813 | C=CC(=O)CC.CCCCC1Cc2cc(OC)ccc2C1=O>>CCCCC1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O | C(CCC)C1C(C2=CC=C(C=C2C1)OC)=O.N12CCCCCC2=NCCC1.C(=C)C(=O)CC>>C(CCC)C1(C(C2=CC=C(C=C2C1)OC)=O)CCC(CC)=O | [CH2:6]=[CH:7][C:8](=[O:9])[CH2:10][CH3:11].[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:12][c:13]2[cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19][c:20]2[C:21]1=[O:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH3:11])[CH2:12][c:13]2[cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19][c:20]2[C:21]1=[O:22] | C=CC(=O)CC.CCCCC1Cc2cc(OC)ccc2C1=O | CCCCC1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O | null | null | O1CCCC1 | C-C Coupling | OtherReaction | c504c0d32586144b6874498db3cc99d4d5bb675e1b2e725385a0386d3f14ac05 | 68a0b2d4768a64505cf15a6dd6bbd75216aef3c50fb86aff9b39341b3e49f06d | O=C1CCc2ccccc21 | [C:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D4;+0:8]1(-[C:7]-[C:6])-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13] | 27.8 | [{"value": 27.8, "product": "C(CCC)C1(C(C2=CC=C(C=C2C1)OC)=O)CCC(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of crude 2-butyl-5-methoxy-1-indanone (218 mg, 1 mmol) in tetrahydrofuran (THF, 2 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.030 mL, 0.2 mmol) and ethyl vinyl ketone (EVK, 0.200 mL, 2 mmol). The resulting solution was stirred under a nitrogen atmosphere at room temperature for 16 hours, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | O1CCCC1 | null | 16 | C=CC(=O)CC.CCCCC1Cc2cc(OC)ccc2C1=O>O1CCCC1>CCCCC1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-13b6e50ba0aa46dbbb22df4807534675 | CCCCC1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O>>CCCCC12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 | C(CCC)C1(C(C2=CC=C(C=C2C1)OC)=O)CCC(CC)=O>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC | O=[C:12]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH3:11])[CH2:21][c:20]2[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]1[CH2:21]2 | CCCCC1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 | null | null | C(C)(=O)O.Cl | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[C;D1;H3:13]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[C;H0;D3;+0:12](-[C;D1;H3:13])-[C:10](=[O;D1;H0:11])-[C:9]-[C:8]-2 | 95.4 | [{"value": 95.4, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 2-butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone (84 mg, 0.28 mmol) in acetic acid (0.5 mL) and 6N HCl (0.5 mL) was stirred and heated in an oil bath at 100° C. for 21 hours. After cooling to room temperature, the reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic phase was... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | C(C)(=O)O.Cl | 100 | null | CCCCC1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O>C(C)(=O)O.Cl>CCCCC12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86276ff0e0a9422aa0299c840223781e | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC.B(Br)(Br)Br.C1=CC=CC=C1>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)O | C[O:17][c:16]1[cH:15][cH:14][c:13]2[c:19]([cH:18]1)[CH2:20][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]1[CH2:20]2 | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | A solution of 9a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (76 mg, 0.267 mmol) in anhydrous CH2Cl2 (2 mL) was placed under a nitrogen atmosphere, cooled in an ice bath, and stirred while 1M BBr3 in CH2Cl2 (0.80 mL, 0.80 mmol) was added by syringe. The cooling bath was removed and the mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | C(Cl)Cl | null | 2 | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)cc1C2>C(Cl)Cl>CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-939af69376254c7286149b31bfef6201 | CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2.NO>>CCCCC12CC/C(=N\O)C(C)=C1c1ccc(O)cc1C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)O.Cl.ON>>C(CCC)C12CC3=CC(=CC=C3C2=C(/C(/CC1)=N/O)C)O | O=[C:8]1[CH2:7][CH2:6][C:5]2([CH2:4][CH2:3][CH2:2][CH3:1])[C:13](=[C:11]1[CH3:12])[c:14]1[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]1[CH2:21]2.[NH2:9][OH:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7]/[C:8](=[N:9]\[OH:10])[C:11]([CH3:12])=[C:13]1[c:14]1[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]1[CH2:21]2 | CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2.NO | CCCCC12CC/C(=N\O)C(C)=C1c1ccc(O)cc1C2 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | d3d236aa4e3e4e208453b21920155e6bd55b5bb5f7260413e9973587997eadd2 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5](=[C:6]-1-[C;D1;H3:7])-[c:8].[NH2;D1;+0:9]-[O;D1;H1:10]>>[C;D1;H3:7]-[C:6]1=[C:5](-[c:8])-[C:4]-[C:3]-[C:2]/[C;H0;D3;+0:1]-1=[N;H0;D2;+0:9]\[O;D1;H1:10] | null | [] | 60 | CELSIUS | null | null | A solution of 9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (60 mg, 0.22 mmol) and hydroxyl amine hydrochloride (77 mg, 1.11 mmol) in anhydrous pyridine (0.5 mL) was stirred under a nitrogen atmosphere at room temperature for 4.3 hours and then heated in an oil bath at 60° C. for 30 minutes. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | N1=CC=CC=C1 | 60 | null | CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2.NO>N1=CC=CC=C1>CCCCC12CC/C(=N\O)C(C)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-348e8a54c7c84684b360fbaec8b6e185 | CCCC=O.COc1ccc2c(c1)CCC2=O>>CCCC=C1Cc2cc(OC)ccc2C1=O | COC=1C=C2CCC(C2=CC1)=O.C(CCC)=O.C(C)(C)NC(C)C.C(CCC)[Li].CCCCC>>C(CCC)=C1C(C2=CC=C(C=C2C1)OC)=O | O=[CH:4][CH2:3][CH2:2][CH3:1].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][CH2:2][CH2:3][CH:4]=[C:5]1[CH2:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[C:15]1=[O:16] | CCCC=O.COc1ccc2c(c1)CCC2=O | CCCC=C1Cc2cc(OC)ccc2C1=O | null | null | O1CCCC1 | C-C Coupling | Aldol condensation | 68e28f9095e1f150f32da6921211b9a27c818a0dd75d077bb5baa7c9b256c798 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | [CH]=C1Cc2ccccc2C1=O | O=[CH;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[CH2;D2;+0:6]-[C:7]-[c:8]:[c:9]-1>>[C:3]-[C:2]-[CH;D2;+0:1]=[C;H0;D3;+0:6]1-[C:7]-[c:8]:[c:9]-[C:5]-1=[O;D1;H0:4] | null | [] | null | null | 15 | MINUTE | A solution of diisopropylamine (0.227 mL, 1.62 mmol) in anhydrous tetrahydrofuran (THF, 15 mL) was placed under a nitrogen atmosphere, cooled in an ice bath, and stirred while a 2.0M solution of butyllithium in pentane (0.771 mL, 1.54 mmol) was added dropwise over 2 minutes. The solution was stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | O1CCCC1 | null | 0.25 | CCCC=O.COc1ccc2c(c1)CCC2=O>O1CCCC1>CCCC=C1Cc2cc(OC)ccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0caa973e2b6a45ab9fd8c25a7a357edd | CC/C=C/C1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O>>CC/C=C/C12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 | C(=C\CC)/C1(C(C2=CC=C(C=C2C1)OC)=O)CCC(CC)=O.[OH-].[Na+]>>C(=C\CC)/C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC | O=[C:12]1[C:5](/[CH:4]=[CH:3]/[CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH3:11])[CH2:21][c:20]2[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19]2>>[CH3:1][CH2:2]/[CH:3]=[CH:4]/[C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]1[CH2:21]2 | CC/C=C/C1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O | CC/C=C/C12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 | null | null | CO | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(/[C:7]=[C:8]/[C:9])-[C:10]-[C:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[C;D1;H3:15]>>[C:9]/[C:8]=[C:7]/[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[C;H0;D3;+0:14](-[C;D1;H3:15])-[C:12](=[O;D1;H0:13])-[C:11]-[C:10]-2 | 35.8 | [{"value": 35.8, "product": "C(=C\\CC)/C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A solution of 2-[(1E)-1-butenyl]-5-methoxy-2-(3-oxopentyl)-1-indanone (199 mg, 0.663 mmol) in methanol (5 mL) was treated with 2N aqueous NaOH (1.6 mL) and the resulting mixture was stirred and heated in an oil bath at 85° C. for 7 hours. After cooling to room temperature, the brown solution was partitioned between EtO... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | CO | 85 | null | CC/C=C/C1(CCC(=O)CC)Cc2cc(OC)ccc2C1=O>CO>CC/C=C/C12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7b694b1a63448cfb05ba1ccd587d001 | CC/C=C/C12CCC(=O)C(C)=C1c1ccc(OC)cc1C2>>CC/C=C/C12CCC(=O)C(C)=C1c1ccc(O)cc1C2 | C(=C\CC)/C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC.Cl.N1=CC=CC=C1>>C(=C\CC)/C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)O | C[O:17][c:16]1[cH:15][cH:14][c:13]2[c:19]([cH:18]1)[CH2:20][C:5]1(/[CH:4]=[CH:3]/[CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]12>>[CH3:1][CH2:2]/[CH:3]=[CH:4]/[C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]1[CH2:20]2 | CC/C=C/C12CCC(=O)C(C)=C1c1ccc(OC)cc1C2 | CC/C=C/C12CCC(=O)C(C)=C1c1ccc(O)cc1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 190 | CELSIUS | null | null | A mixture of 9a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (31.7 mg, 0.112 mmol) and pyridine hydrochloride (384 mg, 3.32 mmol) was placed under a nitrogen atmosphere and heated in an oil bath at 190° C. for 65 minutes. After cooling to room temperature, the reaction mixture was partitione... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | null | 190 | null | CC/C=C/C12CCC(=O)C(C)=C1c1ccc(OC)cc1C2>>CC/C=C/C12CCC(=O)C(C)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81064133f67440459d71cf2f2f14c79e | CCCC=O.COc1ccc2c(c1)CCC2=O>>CCCCC1Cc2cc(OC)ccc2C1=O | Cl.COC=1C=C2CCC(C2=CC1)=O.[OH-].[K+].C(CCC)=O>>C(CCC)C1C(C2=CC=C(C=C2C1)OC)=O | O=[CH:4][CH2:3][CH2:2][CH3:1].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[C:15]1=[O:16] | CCCC=O.COc1ccc2c(c1)CCC2=O | CCCCC1Cc2cc(OC)ccc2C1=O | null | [Pd] | C(C)O | C-C Coupling | OtherReaction | 68e28f9095e1f150f32da6921211b9a27c818a0dd75d077bb5baa7c9b256c798 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1CCc2ccccc21 | O=[CH;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[CH2;D2;+0:6]-[C:7]-[c:8]:[c:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:6]1-[C:7]-[c:8]:[c:9]-[C:5]-1=[O;D1;H0:4] | 53.2 | [{"value": 53.2, "product": "C(CCC)C1C(C2=CC=C(C=C2C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 5-methoxy-1-indanone (25.0 g, 154 mmol), 85% KOH (2.03 g, 30.8 mmol), 10% palladium on activated carbon (2 g), and ethanol (150 mL) was placed under a hydrogen atmosphere and stirred while butyraldehyde (16.7 mL, 185 mmol) was added over 2 minutes. The mixture warmed during the addition. The resulting mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | [Pd].C(C)O | null | 3 | CCCC=O.COc1ccc2c(c1)CCC2=O>[Pd].C(C)O>CCCCC1Cc2cc(OC)ccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6eb19596dc4f425b98b352cad4d4b671 | CCCCC1(CCC(C)=O)Cc2cc(OC)ccc2C1=O>>CCCCC12CCC(=O)C=C1c1ccc(OC)cc1C2 | C(CCC)C1(C(C2=CC=C(C=C2C1)OC)=O)CCC(C)=O.N1CCCC1.C(C)(=O)O>>C(CCC)C12CC3=CC(=CC=C3C2=CC(CC1)=O)OC | O=[C:11]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH3:10])[CH2:20][c:19]2[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:11]1[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][c:19]1[CH2:20]2 | CCCCC1(CCC(C)=O)Cc2cc(OC)ccc2C1=O | CCCCC12CCC(=O)C=C1c1ccc(OC)cc1C2 | null | null | null | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[CH;D2;+0:11]-[C:10](=[O;D1;H0:12])-[C:9]-[C:8]-2 | null | [] | 60 | CELSIUS | null | null | The solution from step 2 was treated with pyrrolidine (6.9 mL, 82 mmol) and acetic acid (4.7 mL, 82 mmol), placed under a nitrogen atmosphere, and stirred with heating in a 60° C. bath for 22 hours. After cooling to room temperature, the reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL). The Et... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | null | 60 | null | CCCCC1(CCC(C)=O)Cc2cc(OC)ccc2C1=O>>CCCCC12CCC(=O)C=C1c1ccc(OC)cc1C2 |
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