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-499c1cc00a404c2bb82dd402c8304336 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1>>COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2O | C(=O)(O)[O-].[Na+].C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)OCC1=CC=C(C=C1)OC)=O.O>>COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)O)=O | COc1ccc(C[O:27][CH:26]2[c:21]3[cH:20][cH:19][c:18]([C@@H:17]4[C@@H:11]([CH2:10]/[CH:9]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:12](=[O:13])[CH2:14][C@H:15]4[OH:16])[cH:23][c:22]3[CH2:24][CH2:25]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][C@H:11]1[C:12](=[O:13])[CH2:14][... | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2O | null | null | ClCCl | Reduction | OtherReaction | c90596e654e5d1e77e11d554a977c19dbfd45f761dbcb2a67a22a5f8c8ab1ef2 | 628b56b3f4fed40b9cc8e2f7565bcae98d5e36a3f75394461dabd987fb619482 | O=C1CC[C@H](c2ccc3c(c2)CCC3)C1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])-[c:4]):c:c:1>>[C:3]-[C:2](-[OH;D1;+0:1])-[c:4] | 434.7 | [{"value": 60.0, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 434.7, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 55 | MINUTE | DDQ (41 mg, 0.18 mmol) was added to a mixture of 15-5 (11 mg, 0.021 mmol) in dichloromethane (3.5 mL)/water (175 μL). After 55 min., saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×50 mL). The combined dichloromethane solution was washed with brine and then was dried ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Secondary alcohol | c1ccccc1 | null | C1CCCC1.c1ccc2c(c1)CCC2 | HO- | ClCCl | null | 0.916667 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1>ClCCl>COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aab96c42632a4a4890d68c2d0cb345b0 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1>>COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2=O | C(=O)(O)[O-].[Na+].C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)OCC1=CC=C(C=C1)OC)=O.ClC(C)Cl>>COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)=O)=O | COc1ccc(C[O:27][CH:26]2[c:21]3[cH:20][cH:19][c:18]([C@@H:17]4[C@@H:11]([CH2:10]/[CH:9]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:12](=[O:13])[CH2:14][C@H:15]4[OH:16])[cH:23][c:22]3[CH2:24][CH2:25]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][C@H:11]1[C:12](=[O:13])[CH2:14][... | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2=O | null | null | ClCCl.O | Functional Group Interconversion | OtherReaction | d0dadbf1f41df81e42cc1b06e031cd4ce01cda1b95de9701c7b81cc85175e3d5 | ff3c0d456b2d4191efb7126f02d8b343330f99a5bd55cfc08cd94367187e2524 | O=C1CC[C@H](c2ccc3c(c2)CCC3=O)C1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[CH;D3;+0:2]2-[C:3]-[C:4]-[c:5]:[c:6]-2:[c:7]):c:c:1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7] | 64.3 | [{"value": 59.0, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.3, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | DDQ (10 mg, 0.041 mmol) was added to a mixture of 15-5 (11 mg, 0.021 mmol) in dichloromethane (0.5 mL)/water (25 μL). After 1 h, dichloroethane (0.5 mL) was added and the reaction was stirred overnight. Saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | c1ccccc1.c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | C1CCCC1.c1ccc2c(c1)CCC2 | HO- | ClCCl.O | null | 1 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1>ClCCl.O>COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bfb2671409546e88e8771b6b2fea5b7 | C=CCc1ccc(O)c(CC=C)c1O>>CCCc1ccc(O)c(CCC)c1O | C(C=C)C1=C(O)C(=CC=C1O)CC=C>>C(CC)C1=C(O)C=CC(=C1O)CCC | [CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([CH2:10][CH:11]=[CH2:12])[c:13]1[OH:14]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([CH2:10][CH2:11][CH3:12])[c:13]1[OH:14] | C=CCc1ccc(O)c(CC=C)c1O | CCCc1ccc(O)c(CCC)c1O | null | [Pd] | CO | Reduction | OtherReaction | f69b32ec19736437d6567a39731061f512e8e67ea9301cdcf93f07d7793003c3 | d69deccbf6585965088073408ee5be8b8c3152f4b9c3604883a5d86aa3bdd693 | c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4].[CH2;D1;+0:5]=[CH;D2;+0:6]-[C:7]-[c:8]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[C:7]-[c:8] | null | [] | null | null | null | null | The product 2,6-bis-allylresorcinol (33.5 gm) was dissolved in methanol and hydrogenated under H2 Pressure (initial pressure 45 psig) over 10% Pd on carbon (300 mg). The reaction mixture was filtered through celite and reduced i. vac. The crude oil was flushed through a short SiO2 gel column eluting with ethyl ether. T... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | null | c1ccccc1 | null | [Pd].CO | null | null | C=CCc1ccc(O)c(CC=C)c1O>[Pd].CO>CCCc1ccc(O)c(CCC)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07cdbdf55f0e4eb6803123ffb55d89c6 | CCCc1c(O)ccc2c(C(F)(F)F)noc12.O=S(=O)(Cl)Cl>>CCCc1c(O)c(Cl)cc2c(C(F)(F)F)noc12 | C(C(C)C)NCC(C)C.C(C(C)C)NCC(C)C.OC1=C(C2=C(C(=NO2)C(F)(F)F)C=C1)CCC.S([O-])(O)=O.[Na+].O1N=CC2=C1C=CC=C2.S(=O)(=O)(Cl)Cl>>ClC=1C(=C(C2=C(C(=NO2)C(F)(F)F)C1)CCC)O | [CH3:1][CH2:2][CH2:3][c:4]1[c:5]([OH:6])[cH:7][cH:9][c:10]2[c:11]([C:12]([F:13])([F:14])[F:15])[n:16][o:17][c:18]12.O=S(=O)(Cl)[Cl:8]>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([OH:6])[c:7]([Cl:8])[cH:9][c:10]2[c:11]([C:12]([F:13])([F:14])[F:15])[n:16][o:17][c:18]12 | CCCc1c(O)ccc2c(C(F)(F)F)noc12.O=S(=O)(Cl)Cl | CCCc1c(O)c(Cl)cc2c(C(F)(F)F)noc12 | null | null | C(C)OCC.C1(=CC=CC=C1)C | Functional Group Interconversion | Chlorination | b7992ebb52d63e770c64ca0975a9b9bafbd1dbe31ad0828e52b61c031d34db6c | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2oncc2c1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].[O;D1;H1:2]-[c:3]1:[c:4]:[c:5]2:[#8;a:6]:[#7;a:7]:[c:8]:[c:9]:2:[c:10]:[cH;D2;+0:11]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:11]1:[c:10]:[c:9]2:[c:8]:[#7;a:7]:[#8;a:6]:[c:5]:2:[c:4]:[c:3]:1-[O;D1;H1:2] | null | [] | null | null | 8 | HOUR | Diisobutylamine (0.8 ml, 0.10 eq) and 6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole (11 gm, 1.0 eq) were dissolved in toluene (275 ml) at room temperature. Slow addition of sulfuryl chloride (4.20 ml, 1.15 eq) results in a suspension which was stirred overnight. Additional diisobutylamine (total 1.6 ml, 0.4 eq) was... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2oncc2c1 | c1ccc2oncc2c1 | c1ccc2oncc2c1 | HCl | C(C)OCC.C1(=CC=CC=C1)C | null | 8 | CCCc1c(O)ccc2c(C(F)(F)F)noc12.O=S(=O)(Cl)Cl>C(C)OCC.C1(=CC=CC=C1)C>CCCc1c(O)c(Cl)cc2c(C(F)(F)F)noc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83d069dc05c04271afbe84952104b3b2 | C=CCOc1ccc(C(=O)c2ccccc2)c(O)c1>>C=CCc1c(O)ccc(C(=O)c2ccccc2)c1O | C(C=C)OC1=CC(=C(C(=O)C2=CC=CC=C2)C=C1)O.ClC1=C(C=CC=C1)Cl>>OC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1CC=C)O | [CH2:1]=[CH:2][CH2:3][O:6][c:5]1[cH:4][c:18]([OH:19])[c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:8][cH:7]1>>[CH2:1]=[CH:2][CH2:3][c:4]1[c:5]([OH:6])[cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1[OH:19] | C=CCOc1ccc(C(=O)c2ccccc2)c(O)c1 | C=CCc1c(O)ccc(C(=O)c2ccccc2)c1O | null | null | null | Miscellaneous | OtherReaction | f9046ab8287acad6d9b914f5f533866252d6845a323cc2516eb4a5b1de541a76 | 58578155da4647eafb0f18a2061753170490dc4f2b17890a513522e28d385731 | O=C(c1ccccc1)c1ccccc1 | [C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[O;D1;H1:9]):[c:10]-[C:11]=[O;D1;H0:12]>>[C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[c;H0;D3;+0:7](:[c:8](-[O;D1;H1:9]):[c:10]-[C:11]=[O;D1;H0:12]):[c:5](-[OH;D1;+0:4]):[c:6] | null | [] | null | null | null | null | Commercially available 4-allyloxy-2-hydroxybenzophenone (15 g) was rearranged by heating under reflux in ortho-dichlorobenzene (60 mL) for 26 hours. The product was isolated by dilution of the reaction mixture with 5 volumes hexanes to give a crystalline product as fine needles.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Allyl | Aromatic alcohol.Allyl | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | C=CCOc1ccc(C(=O)c2ccccc2)c(O)c1>>C=CCc1c(O)ccc(C(=O)c2ccccc2)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dae0fbb51a884e2aa48fba735687cadc | C=CCc1c(O)ccc(C(=O)c2ccccc2)c1O>>CCCc1c(O)ccc(C(=O)c2ccccc2)c1O | OC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1CC=C)O>>OC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1CCC)O | [CH2:1]=[CH:2][CH2:3][c:4]1[c:5]([OH:6])[cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1[OH:19]>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([OH:6])[cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1[OH:19] | C=CCc1c(O)ccc(C(=O)c2ccccc2)c1O | CCCc1c(O)ccc(C(=O)c2ccccc2)c1O | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | bc16a674f12262641e5cd54edc2026446c884c0ddcda2374dddc2ac4d3dae2ab | 6afc5b4ad7d0f8b85f89bd805881fd9206fc3da38639abfb1c97bb82ede31c54 | O=C(c1ccccc1)c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4] | null | [] | null | null | null | null | A solution of 2,4-dihydroxy-3-(2-propenyl)benzophenone (3 g) was reduced under ˜1 atm H2 in ethyl acetate (100 mL) over 10% Pd/C catalyst (0.3 grams) for 3 hours. The product was purified by crystallization from methanol/water. The product is obtained as small yellow plates.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)(=O)OCC | null | null | C=CCc1c(O)ccc(C(=O)c2ccccc2)c1O>[Pd].C(C)(=O)OCC>CCCc1c(O)ccc(C(=O)c2ccccc2)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c83a6e508cf40888e8a12369cb3ade0 | CCCc1cc(C(=O)CC)c(O)c(CCC)c1OC(C(=O)OC)c1ccccc1>>CCCc1cc(C(=O)CC)c(O)c(CCC)c1OC(C(=O)O)c1ccccc1 | OC=1C(=C(OC(C(=O)OC)C2=CC=CC=C2)C(=CC1C(CC)=O)CCC)CCC.[OH-].[Na+]>>OC=1C(=C(OC(C(=O)O)C2=CC=CC=C2)C(=CC1C(CC)=O)CCC)CCC | C[O:22][C:20]([CH:19]([O:18][c:17]1[c:4]([CH2:3][CH2:2][CH3:1])[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH3:10])[c:11]([OH:12])[c:13]1[CH2:14][CH2:15][CH3:16])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)=[O:21]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH3:10])[c:11]([OH:12])[c:13]([CH2:14][CH2:15][CH3:16])[... | CCCc1cc(C(=O)CC)c(O)c(CCC)c1OC(C(=O)OC)c1ccccc1 | CCCc1cc(C(=O)CC)c(O)c(CCC)c1OC(C(=O)O)c1ccccc1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccccc2)cc1 | 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 | null | null | The ester of step 2 (18.6 gm) was hydrolyzed with NaOH (98 ml) as for example 1, step 5.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | CCCc1cc(C(=O)CC)c(O)c(CCC)c1OC(C(=O)OC)c1ccccc1>>CCCc1cc(C(=O)CC)c(O)c(CCC)c1OC(C(=O)O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec11d9e4f3f449f6a915145c8ea66bec | CCC(=O)[O-].CCCc1cccc(CCC)c1O>>CCCc1cc(C(=O)CC)cc(CCC)c1O | C(CC)(=O)[O-].[Na+].C(CC)C1=C(C(=CC=C1)CCC)O>>C(CC)C1=C(C(=CC(=C1)C(CC)=O)CCC)O | [O-][C:7](=[O:8])[CH2:9][CH3:10].[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:11][c:12]([CH2:13][CH2:14][CH3:15])[c:16]1[OH:17]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH3:10])[cH:11][c:12]([CH2:13][CH2:14][CH3:15])[c:16]1[OH:17] | CCC(=O)[O-].CCCc1cccc(CCC)c1O | CCCc1cc(C(=O)CC)cc(CCC)c1O | null | null | OS(=O)(=O)C(F)(F)F | C-C Coupling | OtherReaction | e5396060890e7063846e7fb4a7b028009286093e3288e682a220bc78c8f51cd3 | f600e7da43691f6eafd7566c832dd1dfb3eebdf72a39a998750efa402a8f7cf6 | c1ccccc1 | [C;D1;H3:1]-[C:2]-[C;H0;D3;+0:3](-[O-])=[O;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | Sodium propanoate (0.88 g, 1.5 eq) and 2,6-dipropylphenol (1.09 g, 1.0 eq) were combined in Triflic Acid (5.0 g) as in Example 13, step 1. The resulting waxy solid was purified by chromatography on silica gel using ethyl acetate:hexanes:acetic acid (10:90:1) to give the titled phenol.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | OS(=O)(=O)C(F)(F)F | null | null | CCC(=O)[O-].CCCc1cccc(CCC)c1O>OS(=O)(=O)C(F)(F)F>CCCc1cc(C(=O)CC)cc(CCC)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7592862b4de4400099977859206fead8 | CC(C)Br.COC(=O)Cc1ccc(O)cc1>>COC(=O)Cc1ccc(OC(C)C)cc1 | Cl.OC1=CC=C(C=C1)CC(=O)OC.C(=O)([O-])[O-].[Cs+].[Cs+].BrC(C)C>>CC(C)OC1=CC=C(C=C1)CC(=O)OC | Br[CH:11]([CH3:12])[CH3:13].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]1 | CC(C)Br.COC(=O)Cc1ccc(O)cc1 | COC(=O)Cc1ccc(OC(C)C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccccc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | Methyl (4-hydroxyphenyl)acetate (1.0 g, 1.0 eq), Cs2CO3 (2.15 g, 1.1 eq) and 2-bromopropane (0.565 mL. 1.0 eq) were combined in 100 ml DMF at room temperature. The mixture was stirred overnight. The suspension was poured into 50 mL 1 N HCl and extracted with ethyl acetate. The organic phase was separated and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C)C=O | null | 8 | CC(C)Br.COC(=O)Cc1ccc(O)cc1>CN(C)C=O>COC(=O)Cc1ccc(OC(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f951ff6e45a44e29983784a13e42f834 | CCC(=O)O.CCCc1ccc(O)c(CCC)c1F>>CCCc1cc(C(=O)CC)c(F)c(CCC)c1O | C(CC)(=O)O.FC=1C(=C(C=CC1CCC)O)CCC.FC(S(=O)(=O)O)(F)F>>FC=1C(=C(C(=CC1C(CC)=O)CCC)O)CCC | O[C:7](=[O:8])[CH2:9][CH3:10].[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:11]([OH:18])[c:13]([CH2:14][CH2:15][CH3:16])[c:17]1[F:12]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH3:10])[c:11]([F:12])[c:13]([CH2:14][CH2:15][CH3:16])[c:17]1[OH:18] | CCC(=O)O.CCCc1ccc(O)c(CCC)c1F | CCCc1cc(C(=O)CC)c(F)c(CCC)c1O | null | null | null | Functional Group Interconversion | OtherReaction | 226287c5381c26952dfe91dfeb9f272de32d3e5724429362f80e36413cbcbe19 | fdd617d504c91eca46103a55d487a57bf4aee64556f8d813b4f116bc72575b31 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[C:5]-[c:6]1:[c;H0;D3;+0:7](-[OH;D1;+0:8]):[cH;D2;+0:9]:[c:10]:[c:11](-[C:12]):[c;H0;D3;+0:13]:1-[F;H0;D1;+0:14]>>[C:5]-[c:6]1:[c;H0;D3;+0:7](-[F;H0;D1;+0:14]):[c;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4]):[c:10]:[c:11](-[C:12]):[c;H0;D3;+0:13]:1-[OH;D1... | null | [] | null | null | null | null | Propionic acid (9.07 g, 123 mmol) and 3-fluoro-2,4-dipropylphenol (9.60 g, 49.0 mmol) were mixed in trifluoromethanesulfonic acid (50 mL) as in Example 13, step 1. Purification by chramotography on silica gel using ethyl acetate:hexane (10:90) gave the title compound as a white solid.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Aromatic alcohol | Aromatic halide.Ketone.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CCC(=O)O.CCCc1ccc(O)c(CCC)c1F>>CCCc1cc(C(=O)CC)c(F)c(CCC)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e82600096dac46b5b34ea78698e65332 | O=S(=O)(Cl)CC(F)(F)F.[NH4+]>>NS(=O)(=O)CC(F)(F)F | C(F)(F)(F)CS(=O)(=O)Cl.[NH4+].[OH-]>>C(F)(F)(F)CS(=O)(=O)N | Cl[S:2](=[O:3])(=[O:4])[CH2:5][C:6]([F:7])([F:8])[F:9].[NH4+:1]>>[NH2:1][S:2](=[O:3])(=[O:4])[CH2:5][C:6]([F:7])([F:8])[F:9] | O=S(=O)(Cl)CC(F)(F)F.[NH4+] | NS(=O)(=O)CC(F)(F)F | null | null | O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 76fbc3582e2f63736dd65176b79ffad31881adfa34415872457e21307ad3c8dc | 8d9fe3486c870d18f12e4e21ee2410d7c9641745d38b34bc61fa11f384cef528 | null | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[NH4+;D0:9]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:4]-[S;H0;D4;+0:1](-[NH2;D1;+0:9])(=[O;D1;H0:2])=[O;D1;H0:3] | null | [] | null | null | null | null | The CF3CH2SO2NH2 was prepared by cooling a solution of commercially available CF3CH2SO2Cl (0.6 ml, 1 eq) in CH2Cl2 to 0° C. NH4OH (0.75 ml, 14.8 N, 2 eq) was then added dropwise. The mixture was allowed to warm to room temperature overnight. The reaction was diluted with water and extracted three times with CH2Cl2. The... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | null | HCl | O.C(Cl)Cl | null | null | O=S(=O)(Cl)CC(F)(F)F.[NH4+]>O.C(Cl)Cl>NS(=O)(=O)CC(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38a9717950d0440ea0c81b2cb1362db2 | CCOC(=O)Cc1cccnc1.O=C1CCC(=O)N1Br>>CCOC(=O)C(Br)c1cccnc1 | BrN1C(CCC1=O)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].N1=CC(=CC=C1)CC(=O)OCC.Cl[Si](C)(C)C>>BrC(C(=O)OCC)C=1C=NC=CC1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1.O=C1CCC(=O)N1[Br:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([Br:7])[c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1 | CCOC(=O)Cc1cccnc1.O=C1CCC(=O)N1Br | CCOC(=O)C(Br)c1cccnc1 | null | null | C1CCOC1.O | Functional Group Interconversion | Wohl-Ziegler bromination benzyl secondary | 3f38b5884dced4ec8dd37f9fecb8c81145add99f2a1017bd9519b1712776da1f | 9deb701e8012c4f1578ccc05651bfed620e4410cab5fedb649aa1ac30c26adec | c1ccncc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[Br;H0;D1;+0:1]-[CH;D3;+0:6](-[C:4](=[O;D1;H0:5])-[#8:3]-[C:2])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11] | null | [] | -78 | CELSIUS | 20 | MINUTE | Ethyl 3-pyridylacetate (1.0 g, 1.0 eq) was dissolved in THF (50 mL) and cooled to −78° C. Lithium bis (trimethylsilyl) amide (6.66 mL, 1.1 eq) was added to the reaction and stirred for 20 minutes. Chlorotrimethylsilane (1.44 mL, 1.875 eq) was added at −78° C. and stirred for 20 minutes. N-bromosuccinimide (1.09 g, 1.01... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide.Tertiary amide | Secondary halide | C1CCNC1 | null | c1ccncc1 | HO- | C1CCOC1.O | -78 | 0.333333 | CCOC(=O)Cc1cccnc1.O=C1CCC(=O)N1Br>C1CCOC1.O>CCOC(=O)C(Br)c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1782f4c6e18d44388356e24fbc39135b | C=CCBr.CC(C)=O.Oc1ccc(OCc2ccccc2)cc1>>C=CCc1cc(OCc2ccccc2)cc(CC=C)c1O | C(C1=CC=CC=C1)OC1=CC=C(C=C1)O.C(C=C)Br.C(=O)([O-])[O-].[K+].[K+].CC(=O)C>>C(C=C)C1=C(C(=CC(=C1)OCC1=CC=CC=C1)CC=C)O | Br[CH2:17][CH:18]=[CH2:19].O=[C:2]([CH3:1])[CH3:3].[cH:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16][c:20]1[OH:21]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]([CH2:17][CH:18]=[CH2:19])[c:20]1[OH:21] | C=CCBr.CC(C)=O.Oc1ccc(OCc2ccccc2)cc1 | C=CCc1cc(OCc2ccccc2)cc(CC=C)c1O | null | null | null | C-C Coupling | OtherReaction | c5e563466469107a02e912fa2c3d047d92bc0bea0e97fbdca3bf7287a82c7c13 | e47cdb53db8bcaa27a4325516a44570d192da6f35ef9365fa43284d4b56f7d79 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].O=[C;H0;D3;+0:4](-[CH3;D1;+0:5])-[CH3;D1;+0:6].[O;D1;H1:7]-[c:8]1:[cH;D2;+0:9]:[c:10]:[c:11]:[c:12]:[cH;D2;+0:13]:1>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13](-[CH2;D2;+0:6]-[CH;D2;+0:4]=[CH2;D1;+0:5]):[c:8]:1-[O;D1;H1:7] | null | [] | null | null | null | null | To a solution of starting 4-benzyloxyphenol (20 g) in acetone (800 mL) were added allylbromide (50 mL) and K2CO3 (60 g). The reaction mixture was refluxed overnight. After cooling to the room temperature, the insoluble materials were removed by filtration. The filtrate was concentrated in vac. The residue was partition... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Allyl | Allyl.Allyl | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | null | null | null | C=CCBr.CC(C)=O.Oc1ccc(OCc2ccccc2)cc1>>C=CCc1cc(OCc2ccccc2)cc(CC=C)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cbe90fa9d62e4ab79ebe977953f20624 | C=CCc1cc(OCc2ccccc2)cc(CC=C)c1O.COC(=O)C(Br)c1ccc(Cl)cc1>>C=CCc1cc(O)cc(CC=C)c1OC(C(=O)OC)c1ccc(Cl)cc1 | CCOCC.C(C=C)C1=C(C(=CC(=C1)OCC1=CC=CC=C1)CC=C)O.BrC(C(=O)OC)C1=CC=C(C=C1)Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>>C(C=C)C1=C(OC(C(=O)OC)C2=CC=C(C=C2)Cl)C(=CC(=C1)O)CC=C | c1ccc(C[O:7][c:6]2[cH:5][c:4]([CH2:3][CH:2]=[CH2:1])[c:13]([OH:14])[c:9]([CH2:10][CH:11]=[CH2:12])[cH:8]2)cc1.Br[CH:15]([C:16](=[O:17])[O:18][CH3:19])[c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]1>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([OH:7])[cH:8][c:9]([CH2:10][CH:11]=[CH2:12])[c:13]1[O:14][CH:15]([C:16](=[O:17... | C=CCc1cc(OCc2ccccc2)cc(CC=C)c1O.COC(=O)C(Br)c1ccc(Cl)cc1 | C=CCc1cc(O)cc(CC=C)c1OC(C(=O)OC)c1ccc(Cl)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 53f85fb4df1ea6f44f3a294e10703f62f089f6e01b80df7715f3e9b212492d83 | 548bf445f48f5c4b6c7dcf37d92ce8ff2e6db460b8f4bcaf9e4dc8979044834f | c1ccc(COc2ccccc2)cc1 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:6](:[c:7]):[c:8].[OH;D1;+0:9]-[c:10]1:[c:11]:[c:12]:[c:13](-[O;H0;D2;+0:14]-C-c2:c:c:c:c:c:2):[c:15]:[c:16]:1>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[O;H0;D2;+0:9]-[c:10]1:[c:11]:[c:12]:[c:13](-[OH;D1;+0:14]):[c:15]:[c:16]:1)-[c:6](:[c:7]):[c:8] | null | [] | null | null | 15 | HOUR | To a solution of 2,6-diallyl-4-benzyloxyphenol (200 mg, 1.0 eq) in DMF (8 mL) were added methyl α-bromo-4-chlorobenzeneacetate (190 mg, 1.0 eq) and Cs2CO3 (285 mg, 1.2 eq). The reaction mixture was stirred at room temperature for 15 h, poured into ether, washed with water and brine, dried over MgSO4, filtered, and conc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ether.Aromatic alcohol | Ester.Ether.Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 15 | C=CCc1cc(OCc2ccccc2)cc(CC=C)c1O.COC(=O)C(Br)c1ccc(Cl)cc1>CN(C)C=O>C=CCc1cc(O)cc(CC=C)c1OC(C(=O)OC)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de8f73a85c194ba78978de97959b81eb | CC(=O)c1ccc(F)cc1O.O=C(O)Cc1ccc(Cl)cc1>>O=c1ccc2ccccc2o1 | C([O-])([O-])=O.[K+].[K+].CC(=O)C1=C(C=C(C=C1)F)O.ClC1=CC=C(C=C1)CC(=O)O.C1=CN(C=N1)C(=O)N2C=CN=C2>>O1C(C=CC2=C1C=CC=C2)=O | O=[C:4]([CH3:3])[c:5]1[cH:6][cH:7][c:8](F)[cH:9][c:10]1[OH:11].O[C:2](Cc1ccc(Cl)cc1)=[O:1]>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[o:11]1 | CC(=O)c1ccc(F)cc1O.O=C(O)Cc1ccc(Cl)cc1 | O=c1ccc2ccccc2o1 | null | CN(C)C=1C=CN=CC1 | O.CN(C)C=O | Miscellaneous | OtherReaction | 4e101e46a19ea3ee90b3fc9c267be5b135c81127def38ae3bbc651741dd6f969 | d0c273f5c25e93056ec27ba8a414d05032b56c89b0bcca1a7efb3a560218b0dc | O=c1ccc2ccccc2o1 | Cl-c1:c:c:c(-C-[C;H0;D3;+0:1](-O)=[O;D1;H0:2]):c:c:1.F-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](=O)-[CH3;D1;+0:8]):[c:9](-[OH;D1;+0:10]):[c:11]:1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:8]:[cH;D2;+0:7]:[c:6]2:[c:5]:[c:4]:[cH;D2;+0:3]:[c:11]:[c:9]:2:[o;H0;D2;+0:10]:1 | 38 | [{"value": 38.0, "product": "O1C(C=CC2=C1C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "O1C(C=CC2=C1C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of 4-chlorophenylacetic acid (11.05 g, 64.8 mmol) in DMF (100 mL) was treated with CDI (13.13 g, 81 mmol) in several portions over about 15 minutes and the mixture was stirred until gas evolution had ceased. 4-Fluoro-2-hydroxyacetophenone (5.0 g, 32.4 mmol) was added followed by potassium carbonate (15.7 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Ketone.Aromatic alcohol | null | c1ccccc1.c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HF | CN(C)C=1C=CN=CC1.O.CN(C)C=O | 80 | null | CC(=O)c1ccc(F)cc1O.O=C(O)Cc1ccc(Cl)cc1>CN(C)C=1C=CN=CC1.O.CN(C)C=O>O=c1ccc2ccccc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61a939bb8ae141e4bb2ed9c3a947327d | CC(C)[CH2][Mg][Br].OC1CCC=C1Br>>CC(C)CC1=CCCC1O | BrC=1C(CCC1)O.BrC=1C(CCC1)O.C(C(C)C)[Mg]Br>>C(C(C)C)C=1C(CCC1)O | [Br][Mg][CH2:4][CH:2]([CH3:1])[CH3:3].Br[C:5]1=[CH:6][CH2:7][CH2:8][CH:9]1[OH:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C:5]1=[CH:6][CH2:7][CH2:8][CH:9]1[OH:10] | CC(C)[CH2][Mg][Br].OC1CCC=C1Br | CC(C)CC1=CCCC1O | null | [Ni](Cl)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1 | C-C Coupling | OtherReaction | db82bbef8df76a2432f2b7b688121f836580d3a5c6da8087deb078cabef2b073 | 25890778c2a34dbd8a57fb42f469f5e416c2ea4b1399554507deb7ca9b3263b7 | C1=CCCC1 | Br-[C;H0;D3;+0:1]1=[C:2]-[C:3]-[C:4]-[C:5]-1-[O;D1;H1:6].[Br]-[Mg]-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])-[CH2;D2;+0:7]-[C;H0;D3;+0:1]1=[C:2]-[C:3]-[C:4]-[C:5]-1-[O;D1;H1:6] | null | [] | null | null | null | null | The alcohol (Intermediate D3, 16 mmol) in THF (30 mL) at 0° C. was treated with isobutyl magnesium bromide (40 mmol). The catalyst, 1,3-bis(diphenylphosphino)propane nickel (II) chloride (0.75 mmol) (NiCl2dppp) was added in one portion and the mixture was heated to reflux for 3 h. (see: Organ et al. J. Org. Chem. 1997,... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Alkenyl halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Br-.Mg | [Ni](Cl)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1 | null | null | CC(C)[CH2][Mg][Br].OC1CCC=C1Br>[Ni](Cl)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>CC(C)CC1=CCCC1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6bac18ad000457ea6e76f93c42ca587 | C1=COCCC1.Cc1ccc(S(=O)(=O)[O-])cc1.[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1>>O=C1CCCc2cccc(COC3CCCCO3)c21 | O1CCCC=C1.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1.C(C)(=O)[O-].[Na+]>>O1C(CCCC1)OCC=1C=CC=C2CCCC(C12)=O | [CH:13]1=[CH:14][CH2:15][CH2:16][CH2:17][O:18]1.O=S(=O)([O-:1])[c:2]1[cH:3]c[c:5]([CH3:4])[cH:6][cH:19]1.[O]=[Cr](=[O])([Cl])[O-:12].[nH+]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][O:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:18]3)[c:19]21 | C1=COCCC1.Cc1ccc(S(=O)(=O)[O-])cc1.[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1 | O=C1CCCc2cccc(COC3CCCCO3)c21 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 7601df4ebe7c8306f678a974b9a4f6c9dd5bbe853665a3a426ff89543189bf7c | 28bca55dec68c7a0c75759f892decdd5bb046fceea560a720b79b673ac13228a | O=C1CCCc2cccc(COC3CCCCO3)c21 | O=S(=O)(-[O-;H0;D1:1])-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[CH3;D1;+0:6]):c:[cH;D2;+0:7]:1.[#8:8]1-[C:9]-[C:10]-[C:11]-[CH;D2;+0:12]=[CH;D2;+0:13]-1.[Cl]-[Cr](-[O-;H0;D1:14])(=[O])=[O].[c:15]1:[c:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[nH+]:[cH;D2;+0:19]:1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:7]-[C... | 55 | [{"value": 55.0, "product": "O1C(CCCC1)OCC=1C=CC=C2CCCC(C12)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The diol (Intermediate H3) (2.42 g, 13.5 mmol) was dissolved in CH2Cl2 (75 mL) and reacted with dihydropyran (1.3 mL, 13.8 mmol) and pyridinium para-toluene sulfonate (PPTS) (350 mg, 1.36 mmol) at rt for 18 h. The mixture was concentrated onto SiO2 and purified by chromatography with 10% EtOAc:Hx. The tetrahydropyranyl... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ether | Ketone.Ether.Ether | C1=COCCC1.c1ccccc1.c1cc[n+]cc1 | c1ccc2c(c1)CCCC2.C1CCOCC1 | c1ccc2c(c1)CCCC2.C1CCOCC1 | TsOH.HCl | C(Cl)Cl | null | null | C1=COCCC1.Cc1ccc(S(=O)(=O)[O-])cc1.[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1>C(Cl)Cl>O=C1CCCc2cccc(COC3CCCCO3)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a9e347455ad418da520a0da2e094ddc | CC(=O)Cl.Nc1cccc2c1CCCC2.[O]=[Mn](=[O])(=[O])[O-]>>CC(=O)Nc1cccc2c1C(=O)CCC2 | [NH4+].[Cl-].C(C)(=O)Cl.[O-]S(=O)(=O)[O-].[Mg+2].[O-][Mn](=O)(=O)=O.[K+].C1(=CC=CC=2CCCCC12)N>>O=C1CCCC=2C=CC=C(C12)NC(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:11][CH2:13][CH2:14][CH2:15]2.[O]=[Mn](=[O])([O-])=[O:12]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[C:11](=[O:12])[CH2:13][CH2:14][CH2:15]2 | CC(=O)Cl.Nc1cccc2c1CCCC2.[O]=[Mn](=[O])(=[O])[O-] | CC(=O)Nc1cccc2c1C(=O)CCC2 | null | null | CC(=O)C.O.CCN(CC)CC.C(Cl)(Cl)Cl.C(Cl)Cl | Protection | OtherReaction | 767d72dbcbd04e343c1d04bfc4316ff2bb75efa0566f9b21c8dfa71cf6c6a001 | 89aefbfb6f78410748f2a731669640d685ca87237e823b898811a79392e6c255 | O=C1CCCc2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11].[O-]-[Mn](=[O;H0;D1;+0:12])(=[O])=[O]>>[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:12])-[c:7](:[c:8]):[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:11] | null | [] | 0 | CELSIUS | 2 | HOUR | 5,6,7,8-Tetrahydro-naphthalen-1-ylamine (Intermediate J1, commercially available from Aldrich) (5 mL, 35.3 mmol) was dissolved in CH2Cl2 (40 mL) and treated with NEt3 (10 mL) and acetyl chloride (3.8 mL, 53 mmol) at rt for 1 h. The mixture was diluted in CHCl3 and acidified with sat NH4Cl. The aqueous layer was extract... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Ketone.Secondary amide | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HCl | CC(=O)C.O.CCN(CC)CC.C(Cl)(Cl)Cl.C(Cl)Cl | 0 | 2 | CC(=O)Cl.Nc1cccc2c1CCCC2.[O]=[Mn](=[O])(=[O])[O-]>CC(=O)C.O.CCN(CC)CC.C(Cl)(Cl)Cl.C(Cl)Cl>CC(=O)Nc1cccc2c1C(=O)CCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb8706557d35427e999736d01fcd803a | CC(=O)Nc1cccc2c1C(=O)CCC2>>Nc1cccc2c1C(=O)CCC2 | O=C1CCCC=2C=CC=C(C12)NC(C)=O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>>NC=1C=CC=C2CCCC(C12)=O | CC(=O)[NH:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[O:9])[CH2:10][CH2:11][CH2:12]2>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[O:9])[CH2:10][CH2:11][CH2:12]2 | CC(=O)Nc1cccc2c1C(=O)CCC2 | Nc1cccc2c1C(=O)CCC2 | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=C1CCCc2ccccc21 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6] | 56 | [{"value": 56.0, "product": "NC=1C=CC=C2CCCC(C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.6, "product": "NC=1C=CC=C2CCCC(C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The amide (Intermediate J2, 4.12 g, 20.3 mmol) was heated at 90° C. in 6N HCl (140 mL) for 3 h. The mixture was cooled to rt and Na2CO3 was added in small portions followed by addition of 2N NaOH until the mixture was at pH 8. The aqueous layer was extracted with EtOAc and the organic fractions were combined, washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2c(c1)CCCC2 | HO- | Cl | null | null | CC(=O)Nc1cccc2c1C(=O)CCC2>Cl>Nc1cccc2c1C(=O)CCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8ca59da901b4226a81b5c7540f40e6a | FB(F)F.Nc1cccc2c1C(=O)CCC2>>O=C1CCCc2cccc(F)c21 | N(=O)OC(C)(C)C.NC=1C=CC=C2CCCC(C12)=O.B(F)(F)F.CCOCC>>FC=1C=CC=C2CCCC(C12)=O | FB(F)[F:11].N[c:10]1[cH:9][cH:8][cH:7][c:6]2[c:12]1[C:2](=[O:1])[CH2:3][CH2:4][CH2:5]2>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][c:10]([F:11])[c:12]21 | FB(F)F.Nc1cccc2c1C(=O)CCC2 | O=C1CCCc2cccc(F)c21 | null | null | C(Cl)Cl.CCCCC | Functional Group Interconversion | OtherReaction | 3ef279fffa325c85794079ae07ad71ae4cf8f50c0b924a8c49d6ef3025178107 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | O=C1CCCc2ccccc21 | F-B(-F)-[F;H0;D1;+0:1].N-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](:[c:6])-[C:7](=[O;D1;H0:8])-[C:9]>>[C:9]-[C:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c;H0;D3;+0:2](-[F;H0;D1;+0:1]):[c:3]:[c:4] | null | [] | 0 | CELSIUS | 10 | MINUTE | The amine (Intermediate J3, 1.83 g, 11.3 mmol) in CH2Cl2 (17 mL) was added to BF3.OEt2 (2.80 mL, 22.1 mmol) at −15° C. More CH2Cl2 (20 mL) was added to the precipitate. Next, t-butyl nitrite (1.8 mL, 12.9 mmol) in CH2Cl2 (20 mL) was added at −15° C. and stirred for 10 min. and at 0° C. for 20 m. The mixture was diluted... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HF.B | C(Cl)Cl.CCCCC | 0 | 0.166667 | FB(F)F.Nc1cccc2c1C(=O)CCC2>C(Cl)Cl.CCCCC>O=C1CCCc2cccc(F)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e74f4b9a84246f1b5d7ef55e09714c0 | c1ccc(COCCC2CCC3(CC2)OCCO3)cc1>>O=C1CCC(CCOCc2ccccc2)CC1 | C(C1=CC=CC=C1)OCCC1CCC2(OCCO2)CC1.O.CC=1C=CC(=CC1)S(=O)(=O)O>>C(C1=CC=CC=C1)OCCC1CCC(CC1)=O | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[CH2:16][CH2:17]2>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | c1ccc(COCCC2CCC3(CC2)OCCO3)cc1 | O=C1CCC(CCOCc2ccccc2)CC1 | null | null | CC(=O)C | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCC(CCOCc2ccccc2)CC1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | 97 | [{"value": 97.0, "product": "C(C1=CC=CC=C1)OCCC1CCC(CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-(2-Benzyloxy-ethyl)-1,4-dioxa-spiro[4.5]decane (Intermediate K1, 1.02 g, 3.70 mmol) (prepared in accordance with the publication Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016, incorporated herein by reference) was dissolved in acetone (100 mL): H2O (5 mL) and reacted with TsOH (140 mg, 0.74 mmol) at 45° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | CC(=O)C | null | null | c1ccc(COCCC2CCC3(CC2)OCCO3)cc1>CC(=O)C>O=C1CCC(CCOCc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37e41d6c8bde4a8c90ee4691de966a73 | COC(=O)C#N.O=C1CCC(CCOCc2ccccc2)CC1>>COC(=O)C1CCCCC1 | C(#N)C(=O)OC.CN(C)P(=O)(N(C)C)N(C)C.[Li+].CC(C)[N-]C(C)C.C(C1=CC=CC=C1)OCCC1CCC(CC1)=O>>COC(=O)C1CCCCC1 | N#C[C:3]([O:2][CH3:1])=[O:4].O=[C:8]1[CH2:7][CH2:6][CH:5](CCOCc2ccccc2)[CH2:10][CH2:9]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | COC(=O)C#N.O=C1CCC(CCOCc2ccccc2)CC1 | COC(=O)C1CCCCC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 928e825e225c84955bd59aed5069293c703110ef34100e7e6a88abac42c39cf7 | e6602ab2673207a87d130997833085ef464dfa62e8dfa722678056077bfe8908 | C1CCCCC1 | N#C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].O=[C;H0;D3;+0:5]1-[C:6]-[C:7]-[CH;D3;+0:8](-C-C-O-C-c2:c:c:c:c:c:2)-[C:9]-[C:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:8]1-[C:9]-[C:10]-[CH2;D2;+0:5]-[C:6]-[C:7]-1 | null | [] | 0 | CELSIUS | null | null | A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 min. before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (CNCO2Me, 4.1 mL, 85 mmol) was added and the mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Nitrile | Ester | C1CCCCC1.c1ccccc1 | C1CCCCC1 | C1CCCCC1 | HO- | C1CCOC1 | 0 | null | COC(=O)C#N.O=C1CCC(CCOCc2ccccc2)CC1>C1CCOC1>COC(=O)C1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16fa2f13876a42159089e1648883c1e5 | CCI.COC(=O)C1CC(CCOCc2ccccc2)CCC1=O>>CCC1(C(=O)OC)CC(CCOCc2ccccc2)CCC1=O | COC(=O)C1C(CCC(C1)CCOCC1=CC=CC=C1)=O.C[O-].[Na+].C[O-].[Na+].C(C)I.ICC>>COC(=O)C1(C(CCC(C1)CCOCC1=CC=CC=C1)=O)CC | I[CH2:2][CH3:1].[CH:3]1([C:4](=[O:5])[O:6][CH3:7])[CH2:8][CH:9]([CH2:10][CH2:11][O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21][C:22]1=[O:23]>>[CH3:1][CH2:2][C:3]1([C:4](=[O:5])[O:6][CH3:7])[CH2:8][CH:9]([CH2:10][CH2:11][O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21... | CCI.COC(=O)C1CC(CCOCc2ccccc2)CCC1=O | CCC1(C(=O)OC)CC(CCOCc2ccccc2)CCC1=O | null | null | CO | C-C Coupling | OtherReaction | deecb6e0e045bc39174217ca5e58aac9964e4446522d6e6b0f2101d43cb988e9 | 61bad66347ae366bfd0a2cd3779dd3d0c29125e97564b97243e11258be3b2a9f | O=C1CCC(CCOCc2ccccc2)CC1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[C:11]-[C:12]>>[C:3]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:6](-[CH2;D2;+0:1]-[C;D1;H3:2])(-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[C:11]-[C:12] | null | [] | null | null | 48 | HOUR | A mixture of 5-(2-benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester in anhydrous MeOH (10 mL) was reacted with NaOMe solution (16.6 mL, 8.28 mmol) at rt for 15 min. Iodoethane (2.76 mL, 34.5 mmol) was added via syringe and the mixture was stored at rt for 48 h. Another portion of NaOMe (8.3 mmol) and EtI (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HI | CO | null | 48 | CCI.COC(=O)C1CC(CCOCc2ccccc2)CCC1=O>CO>CCC1(C(=O)OC)CC(CCOCc2ccccc2)CCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a5132735e67540d7a278e6269fdf07ee | CCC1CC(CCOCc2ccccc2)CCC1(C)O>>CCC1=C(C)CCC(CCOCc2ccccc2)C1 | C(C1=CC=CC=C1)OCCC1CC(C(CC1)(O)C)CC.S(=O)(=O)(C1=CC=C(C)C=C1)O.O.[O-]S(=O)(=O)[O-].[Mg+2]>>C(C)C=1CC(CCC1C)CCOCC1=CC=CC=C1 | O[C:4]1([CH3:5])[CH:3]([CH2:2][CH3:1])[CH2:19][CH:8]([CH2:9][CH2:10][O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:7][CH2:6]1>>[CH3:1][CH2:2][C:3]1=[C:4]([CH3:5])[CH2:6][CH2:7][CH:8]([CH2:9][CH2:10][O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1 | CCC1CC(CCOCc2ccccc2)CCC1(C)O | CCC1=C(C)CCC(CCOCc2ccccc2)C1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bb751e8d8bac081516d1433e6fec088b316018c4b9e2465f1f9c878bad0b1e7c | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=CCC(CCOCc2ccccc2)CC1 | O-[C;H0;D4;+0:1]1(-[C;D1;H3:2])-[C:3]-[C:4]-[C:5]-[C:6]-[CH;D3;+0:7]-1-[C:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[C:8]-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]-[C:5]-[C:6]-1 | 71 | [{"value": 71.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-(2-benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester in anhydrous MeOH (10 mL) was reacted with NaOMe solution (16.6 mL, 8.28 mmol) at rt for 15 min. Iodoethane (2.76 mL, 34.5 mmol) was added via syringe and the mixture was stored at rt for 48 h. Another portion of NaOMe (8.3 mmol) and EtI (... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | C1CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | null | CCC1CC(CCOCc2ccccc2)CCC1(C)O>C1=CC=CC=C1>CCC1=C(C)CCC(CCOCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-453edea139244baf9c9ab10628a42515 | CCC1CC(CCOCc2ccccc2)CCC1(C)O>>CCC1=C(C)CCC(CC=O)C1 | C(C1=CC=CC=C1)OCCC1CC(C(CC1)(O)C)CC.CCN(CC)CC.C(C1=CC=CC=C1)OCCC1CC(C(CC1)(O)C)CC.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(C)C=1CC(CCC1C)CC=O | O[C:4]1([CH3:5])[CH:3]([CH2:2][CH3:1])[CH2:12][CH:8]([CH2:9][CH2:10][O:11]Cc2ccccc2)[CH2:7][CH2:6]1>>[CH3:1][CH2:2][C:3]1=[C:4]([CH3:5])[CH2:6][CH2:7][CH:8]([CH2:9][CH:10]=[O:11])[CH2:12]1 | CCC1CC(CCOCc2ccccc2)CCC1(C)O | CCC1=C(C)CCC(CC=O)C1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | be4941a18e7a4255bfefcc67f8959fb712bcee80410bba3c57cbe2980db0414f | 4426f7f4a41437378342710cbad6905f9467a7d2ab3100172eaffaec02d8e0f9 | C1=CCCCC1 | O-[C;H0;D4;+0:1]1(-[C;D1;H3:2])-[C:3]-[C:4]-[C:5](-[C:6]-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-C-c2:c:c:c:c:c:2)-[C:9]-[CH;D3;+0:10]-1-[C:11]-[C;D1;H3:12]>>[C;D1;H3:12]-[C:11]-[C;H0;D3;+0:10]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]-[C:5](-[C:6]-[CH;D2;+0:7]=[O;H0;D1;+0:8])-[C:9]-1 | null | [] | null | null | 40 | MINUTE | The deprotected alcohol was oxidized by the standard “Swern” procedure (Mancuso, Synthesis 1981 p165, incorporated herein by reference) as follows: The alcohol (5 mmol) was added to a solution of oxalyl chloride (3.5 mL, 7.0 mmol) in CH2Cl2 (30 mL) with DMSO (0.64 mL, 9.0 mmol) at −78° C. After 40 min., NEt3 (2.50 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary alcohol | Aldehyde | C1CCCCC1.c1ccccc1 | C1=CCCCC1 | C1=CCCCC1 | HO- | C(Cl)Cl | null | 0.666667 | CCC1CC(CCOCc2ccccc2)CCC1(C)O>C(Cl)Cl>CCC1=C(C)CCC(CC=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2ed4b52ee0845be8a8cce8c441467cb | CC(C)(C)[Si](C)(C)Cl.CN(C)S(=O)(=O)n1ccnc1>>CN(C)S(=O)(=O)n1ccnc1[Si](C)(C)C(C)(C)C | CN(S(=O)(=O)N1C=NC=C1)C.[Li]CCCC.[Si](C)(C)(C(C)(C)C)Cl>>CN(S(=O)(=O)N1C(=NC=C1)[Si](C)(C)C(C)(C)C)C | Cl[Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[n:7]1[cH:8][cH:9][n:10][cH:11]1>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[n:7]1[cH:8][cH:9][n:10][c:11]1[Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18] | CC(C)(C)[Si](C)(C)Cl.CN(C)S(=O)(=O)n1ccnc1 | CN(C)S(=O)(=O)n1ccnc1[Si](C)(C)C(C)(C)C | null | null | C1CCOC1.O | Functional Group Interconversion | OtherReaction | 2a4b40f1b9ebeb08c29f68284298974d85bccd40abdd83eda0860c5d43fa28d0 | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | c1c[nH]cn1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#16:8]-[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[cH;D2;+0:13]:1>>[#16:8]-[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[c;H0;D3;+0:13]:1-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | -78 | CELSIUS | 24 | HOUR | Imidazole (Intermediate L1, available from Aldrich, 20.0 g, 0.29 mol), triethylamine (41.0 mL, 0.29 mol) and N,N-dimethylsulfamoyl chloride (31.6 mL, 0.29 mol) were added to benzene (320 mL). The reaction was stirred for 48 h at rt and then filtered. The filtrate was collected and concentrated under reduced pressure. V... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1 | HCl | C1CCOC1.O | -78 | 24 | CC(C)(C)[Si](C)(C)Cl.CN(C)S(=O)(=O)n1ccnc1>C1CCOC1.O>CN(C)S(=O)(=O)n1ccnc1[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34d736d2a0ea4ad099e56c5998df35eb | C=COCC.OC1CCC=C1Br>>C=COC1CCC=C1Br | BrC=1C(CCC1)O.BrC=1C(CCC1)O.C(=C)OCC>>BrC1=CCCC1OC=C | CCO[CH:2]=[CH2:1].[OH:3][CH:4]1[CH2:5][CH2:6][CH:7]=[C:8]1[Br:9]>>[CH2:1]=[CH:2][O:3][CH:4]1[CH2:5][CH2:6][CH:7]=[C:8]1[Br:9] | C=COCC.OC1CCC=C1Br | C=COC1CCC=C1Br | null | [Hg](OC(=O)C)OC(=O)C | null | Acylation | OtherReaction | 9f1a8de39cf5a08a1f44abee84b9664c807b2fd8724957eb8629cb322ac3bf03 | 60fd153f0b02c0d51bbf266782eeb8125a802a18d05f2f324ecdcbf97326001e | C1=CCCC1 | C-C-O-[CH;D2;+0:1]=[C;D1;H2:2].[Br;D1;H0:3]-[C:4]1=[C:5]-[C:6]-[C:7]-[C:8]-1-[OH;D1;+0:9]>>[Br;D1;H0:3]-[C:4]1=[C:5]-[C:6]-[C:7]-[C:8]-1-[O;H0;D2;+0:9]-[CH;D2;+0:1]=[C;D1;H2:2] | null | [] | null | null | null | null | A solution of 2-bromo-cyclopent-2-enol (Intermediate D3) (21.7 g, 133.1 mmol) in ethyl vinyl ether (300 mL) was treated with Hg(OAc)2 (31.8 g, 99 mmol) at rt for 60 h. The mixture was quenched with 5% NaOH (150 mL) and filtered through celite. The residue was concentrated to yield 1-bromo-5-vinyloxy-cyclopentene as a p... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Vinyl | Ether | null | null | C1=CCCC1 | HO- | [Hg](OC(=O)C)OC(=O)C | null | null | C=COCC.OC1CCC=C1Br>[Hg](OC(=O)C)OC(=O)C>C=COC1CCC=C1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b08eddab25a944edabedd2575e1e1f78 | COC(C)(OC)N(C)C.OC1CCC=C1Br>>CN(C)C(=O)CC1CCC=C1Br | BrC=1C(CCC1)O.BrC=1C(CCC1)O.COC(C)(N(C)C)OC>>BrC=1C(CCC1)CC(=O)N(C)C | CO[C:4]([N:2]([CH3:1])[CH3:3])([O:5]C)[CH3:6].O[CH:7]1[CH2:8][CH2:9][CH:10]=[C:11]1[Br:12]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]=[C:11]1[Br:12] | COC(C)(OC)N(C)C.OC1CCC=C1Br | CN(C)C(=O)CC1CCC=C1Br | null | null | C1(=CC(=CC=C1)C)C | Acylation | OtherReaction | 472efbd11bccde21c77e60699870409b373bfa9a687d07c8eab1af485f3a91e4 | af349c417be477b4d858dc01708167320fccf28f33d370d57c6d20ba9e230b4c | C1=CCCC1 | C-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[O;H0;D2;+0:3]-C)-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].O-[CH;D3;+0:7]1-[C:8]-[C:9]-[C:10]=[C:11]-1-[Br;D1;H0:12]>>[Br;D1;H0:12]-[C:11]1=[C:10]-[C:9]-[C:8]-[CH;D3;+0:7]-1-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6] | 63 | [{"value": 63.0, "product": "BrC=1C(CCC1)CC(=O)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "BrC=1C(CCC1)CC(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-cyclopent-2-enol (Intermediate D3) (2.18 g, 13.4 mmol) and N,N-dimethylacetamide dimethyl acetal (3.5 mL, 21.5 mmol) in m-xylene (˜20 mL) were heated to 140° C. for 14 h. The mixture was freed of solvent and the residue was purified on a column of silica gel with 30% to 50% EtOAc:hexanes to give 2-(2-bromo-cycl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol | Tertiary amide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | HO- | C1(=CC(=CC=C1)C)C | null | null | COC(C)(OC)N(C)C.OC1CCC=C1Br>C1(=CC(=CC=C1)C)C>CN(C)C(=O)CC1CCC=C1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08e867a4674e4c02a3f0795e25c3850a | CN(C)C(=O)CC1CCC=C1Br>>OCCC1CCC=C1Br | BrC=1C(CCC1)CC(=O)N(C)C.C(C)[BH-](CC)CC.[Li+]>>BrC=1C(CCC1)CCO | CN(C)[C:2](=[O:1])[CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]=[C:8]1[Br:9]>>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]=[C:8]1[Br:9] | CN(C)C(=O)CC1CCC=C1Br | OCCC1CCC=C1Br | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 0c75196bc326a5f4df5281c5aa6ae5cdc4819d93f21e68fb7ca3f026ca65886c | cfd0fcbb4b1cf020b5a9adf1c1aee54d845237b6f4e1af15a68ce24628b71452 | C1=CCCC1 | C-N(-C)-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]-[C:5]=[C:6]>>[C:6]=[C:5]-[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 58 | [{"value": 58.0, "product": "BrC=1C(CCC1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(2-Bromo-cyclopent-2-enyl)-N,N-dimethyl-acetamide (Intermediate FOUR1) (1.93 g, 8.3 mmol) in THF (50 mL) was reacted with lithium triethylborohydride (19 mL, 1 M in THF) at 0° C. for 1 h. The mixture was treated with an aqueous work-up and the resultant alcohol was purified by column chromatography to give 0.92 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Primary alcohol | null | null | C1=CCCC1 | Other | C1CCOC1 | null | null | CN(C)C(=O)CC1CCC=C1Br>C1CCOC1>OCCC1CCC=C1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ee325071a0d46e99c30139f1c8099af | OB(O)c1ccccc1F.OCCC1CCC=C1Br>>OCCC1CCC=C1c1ccccc1F | BrC=1C(CCC1)CCO.C(=O)([O-])[O-].[Na+].[Na+].FC1=C(C=CC=C1)B(O)O>>FC1=C(C=CC=C1)C=1C(CCC1)CCO | OB(O)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15].Br[C:8]1=[CH:7][CH2:6][CH2:5][CH:4]1[CH2:3][CH2:2][OH:1]>>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]=[C:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15] | OB(O)c1ccccc1F.OCCC1CCC=C1Br | OCCC1CCC=C1c1ccccc1F | 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.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=... | CCO.O.C1=CC=CC=C1 | C-C Coupling | Suzuki coupling with boronic acids | 8b39a68e12ea3ce139cd616a612024de0f2d741f1d7eb710bb082906f1f12f29 | 5a0296c84d2188f496a7851efee830bbda9aa21de5f6b9e031f92f0a517689c7 | C1=C(c2ccccc2)CCC1 | Br-[C;H0;D3;+0:1]1=[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]>>[C:6]-[C:5]1-[C:4]-[C:3]-[C:2]=[C;H0;D3;+0:1]-1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12] | null | [] | 80 | CELSIUS | null | null | 2-(2-Bromo-cyclopent-2-enyl)-ethanol Intermediate FIVE1 (1.21 g, 6.33 mmol) in benzene (40 mL), and Na2CO3 (7 mL, 2M) was treated with a solution of 2-fluorophenylboronic acid (1.08 g, 7.72 mmol) in EtOH (28 mL). Tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4 (0.38 g, 5 mol %) was added and the mixture was heated ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Boronic acid | null | c1ccccc1.C1=CCCC1 | C1=CCCC1.c1ccccc1 | C1=CCCC1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=... | 80 | null | OB(O)c1ccccc1F.OCCC1CCC=C1Br>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.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=... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbc0d9ebb62a4b7f88776da007ed6142 | CCOC1=CC(=O)CC1.O=C1CCC(=O)N1Br>>CCOC1=C(Br)C(=O)CC1 | C(C)OC1=CC(CC1)=O.C1CC(=O)N(C1=O)Br>>BrC=1C(CCC1OCC)=O | [CH3:1][CH2:2][O:3][C:4]1=[CH:5][C:7](=[O:8])[CH2:9][CH2:10]1.O=C1CCC(=O)N1[Br:6]>>[CH3:1][CH2:2][O:3][C:4]1=[C:5]([Br:6])[C:7](=[O:8])[CH2:9][CH2:10]1 | CCOC1=CC(=O)CC1.O=C1CCC(=O)N1Br | CCOC1=C(Br)C(=O)CC1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 9e1015dee387752fede3530dfce87ae0ed0bc8bdfc02d155d60141e6bf3e07a5 | 91b04554311f4a27d2463e6f0477568ffd575c02d8acaa1ad2eb9195fa41deab | O=C1C=CCC1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3]1=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-1>>[#8:2]-[C:3]1=[C;H0;D3;+0:4](-[Br;H0;D1;+0:1])-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-1 | null | [] | null | null | null | null | 3-Ethoxy-cyclopent-2-enone (Intermediate NINE1) (commercially available from Aldrich) (10.0 g, 77.6 mmol) in carbon tetrachloride (15 mL) at 0° C. was treated with NBS (15.3 g, ˜85 mmol) added portion-wise over 30 m. After 1 h at 0° C. the mixture was partitioned between CH2Cl2 and saturated NaHCO3. The aqueous layer w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide.Tertiary amide | Alkenyl halide | C1=CCCC1.C1CCNC1 | C1=CCCC1 | C1=CCCC1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | CCOC1=CC(=O)CC1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CCOC1=C(Br)C(=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b99ecc263fc43ae8cb7d0f030d361c9 | CCOC1=C(Br)C(=O)CC1.OB(O)c1ccc(F)cc1>>CCOC1=C(c2ccc(F)cc2)C(=O)CC1 | BrC=1C(CCC1OCC)=O.C(=O)([O-])[O-].[K+].[K+].FC1=CC=C(C=C1)B(O)O>>C(C)OC1=C(C(CC1)=O)C1=CC=C(C=C1)F | Br[C:5]1=[C:4]([O:3][CH2:2][CH3:1])[CH2:16][CH2:15][C:13]1=[O:14].OB(O)[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4]1=[C:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[C:13](=[O:14])[CH2:15][CH2:16]1 | CCOC1=C(Br)C(=O)CC1.OB(O)c1ccc(F)cc1 | CCOC1=C(c2ccc(F)cc2)C(=O)CC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=... | CCO.O.C1=CC=CC=C1.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | f7bba2cceceb9f43c641f927a7f9afed99196e4de44cb21ace80bae0c7d3e127 | 8b2fd2c710285a8e42ec4e306f128a23a05d3000a0fcad7f4f9c1377cd9b6157 | O=C1CCC=C1c1ccccc1 | Br-[C;H0;D3;+0:1]1=[C:2](-[#8:3])-[C:4]-[C:5]-[C:6]-1=[O;D1;H0:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#8:3]-[C:2]1=[C;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[C:6](=[O;D1;H0:7])-[C:5]-[C:4]-1 | 70 | [{"value": 70.0, "product": "C(C)OC1=C(C(CC1)=O)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "C(C)OC1=C(C(CC1)=O)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 2-Bromo-3-ethoxy-cyclopent-2-enone (Intermediate NINE2) (10.5 g, 51.2 mmol) and K2CO3 (14.2 g, 102 mmol) in toluene (100 mL), benzene (100 mL) and H2O (50 mL) was treated with a solution of 4-fluorophenylboronic acid (9.31 g, 66.5) in EtOH (100 mL). Tetrakis(triphenylphosphine)palladium(0) Pd(PPh3)4 (3 g, 2.6 mmol), bi... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Boronic acid | Ketone | C1=CCCC1.c1ccccc1 | C1=CCCC1.c1ccccc1 | C1=CCCC1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=... | 100 | null | CCOC1=C(Br)C(=O)CC1.OB(O)c1ccc(F)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=C... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f410f80b3f0a4b32a915abb183781321 | CC1=C(Br)C(=O)CC1.N#Cc1ccc(B(O)O)cc1>>CC1=C(c2ccc(C#N)cc2)C(=O)CC1 | BrC=1C(CCC1C)=O.C(=O)([O-])[O-].[K+].[K+].C(#N)C1=CC=C(C=C1)B(O)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CC1=C(C(CC1)=O)C1=CC=C(C#N)C=C1 | Br[C:3]1=[C:2]([CH3:1])[CH2:15][CH2:14][C:12]1=[O:13].OB(O)[c:4]1[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1>>[CH3:1][C:2]1=[C:3]([c:4]2[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]2)[C:12](=[O:13])[CH2:14][CH2:15]1 | CC1=C(Br)C(=O)CC1.N#Cc1ccc(B(O)O)cc1 | CC1=C(c2ccc(C#N)cc2)C(=O)CC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=... | CCO.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | f7bba2cceceb9f43c641f927a7f9afed99196e4de44cb21ace80bae0c7d3e127 | 8b2fd2c710285a8e42ec4e306f128a23a05d3000a0fcad7f4f9c1377cd9b6157 | O=C1CCC=C1c1ccccc1 | Br-[C;H0;D3;+0:1]1=[C:2](-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-1=[O;D1;H0:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[C;D1;H3:3]-[C:2]1=[C;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[C:6](=[O;D1;H0:7])-[C:5]-[C:4]-1 | null | [] | 80 | CELSIUS | null | null | 2-Bromo-3-methyl-cyclopent-2-enone (Intermediate TEN1) (commercially available from Aldrich) (2.04 g, 11.4 mmol) and K2CO3 (3.16 g in 11 mL H2O) in toluene (45 mL) was treated with a solution 4-cyanophenylboronic acid (commercially available from Aldrich) (2.2 g, 15 mmol) in EtOH (27 mL). Tetrakis(triphenylphosphine)pa... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Boronic acid | Ketone | C1=CCCC1.c1ccccc1 | C1=CCCC1.c1ccccc1 | C1=CCCC1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=... | 80 | null | CC1=C(Br)C(=O)CC1.N#Cc1ccc(B(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=C... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5cb5054aa9ad4c07b38d5b7d2bbe5aca | OCCC1Cc2ccccc2C1>>O=CCC1Cc2ccccc2C1 | C1C(CC2=CC=CC=C12)CCO.C[N+]1(CCOCC1)[O-].C1C(CC2=CC=CC=C12)CC(=O)O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C1C(CC2=CC=CC=C12)CC=O | [OH:1][CH2:2][CH2:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12]1>>[O:1]=[CH:2][CH2:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12]1 | OCCC1Cc2ccccc2C1 | O=CCC1Cc2ccccc2C1 | null | CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | CC#N.C1CCOC1.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2c(c1)CCC2 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | null | [] | null | null | 16 | HOUR | Use of indan-2-yl-acetic acid (commercially available from Lancaster) (Intermediate SEVENTEEN-1) (1.58 g, 8.88 mmol) in THF (15 mL) was added dropwise to a solution of LiAlH4 (9 mL, 1M in Et2O) in THF (10 mL) at 0° C. The mixture was reacted for 2 h at rt and quenched with Rochelle's salt solution and extracted with Et... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2c(c1)CCC2 | null | CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.CC#N.C1CCOC1.C(Cl)Cl | null | 16 | OCCC1Cc2ccccc2C1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.CC#N.C1CCOC1.C(Cl)Cl>O=CCC1Cc2ccccc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-21761f62448e4eaeb88a57c0e17395ff | COC(=O)OC.O=C1CCc2cc(F)ccc21>>COC(=O)C1Cc2ccc(F)cc2C1 | Cl.[H-].[Na+].COC(OC)=O.FC=1C=C2CCC(C2=CC1)=O>>COC(=O)C1CC2=CC=C(C=C2C1)F | CO[C:3]([O:2][CH3:1])=[O:4].O=[C:6]1[CH2:5][CH2:14][c:13]2[c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12]2>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]2[CH2:14]1 | COC(=O)OC.O=C1CCc2cc(F)ccc21 | COC(=O)C1Cc2ccc(F)cc2C1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2890360cfb4b3d777952995f9ea6fb59f6a398984fc169af8dcfcef1a3752370 | fa68f4aa0d3109d3a74ccba0f7352d8a6ecbc181d17439eb72406023cade9696 | c1ccc2c(c1)CCC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].O=[C;H0;D3;+0:5]1-[CH2;D2;+0:6]-[C:7]-[c:8]:[c:9]-1:[c:10]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:6]1-[C:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:5]-1 | null | [] | 65 | CELSIUS | 18 | HOUR | To a mixture of NaH (2.64 g, 66 mmol) in dimethylcarbonate (4.2 mL, 50 mmol) in THF (30 mL) was added a solution of 5-fluoroindanone (commercially available from Aldrich) (5 g, 33 mmol). After 30 m at 65° C. the mixture was cooled to rt, acidified with HCl (aq) and extracted with Et2O or EtOAc. The organic layers were ... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C1CCOC1 | 65 | 18 | COC(=O)OC.O=C1CCc2cc(F)ccc21>C1CCOC1>COC(=O)C1Cc2ccc(F)cc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7bef4df5984842bd9e09da4202b7770b | COC(=O)OC.O=C1CCc2cc(Br)ccc21>>COC(=O)C1Cc2cc(Br)ccc2C1=O | BrC=1C=C2CCC(C2=CC1)=O.[H-].[Na+].COC(OC)=O>>COC(=O)C1C(C2=CC=C(C=C2C1)Br)=O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15] | COC(=O)OC.O=C1CCc2cc(Br)ccc21 | COC(=O)C1Cc2cc(Br)ccc2C1=O | null | null | null | C-C Coupling | OtherReaction | c2c31337dfb867d8c28bc65df0ad4496f817a712a58e176523b47d7fdb6e4f91 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | O=C1CCc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | null | [] | null | null | null | null | Use of 5-bromo-indan-1-one (Intermediate NINETEEN-1) in a reaction with NaH and dimethylcarbonate (refer to procedures in Method EIGHTEEN) produced 5-bromo-1-oxo-indan-2-carboxylic acid methyl ester (Intermediate NINETEEN-2). A solution of 5-bromo-1-oxo-indan-2-carboxylic acid methyl ester (4.75 g, 17.7 mmol) in TFA (8... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | null | null | null | COC(=O)OC.O=C1CCc2cc(Br)ccc21>>COC(=O)C1Cc2cc(Br)ccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dcd109e13fcc40fbb23bd72b4524be9c | COC(=O)C1Cc2cc(Br)ccc2C1=O>>COC(=O)C1Cc2ccc(Br)cc2C1 | COC(=O)C1C(C2=CC=C(C=C2C1)Br)=O.C(C)[SiH](CC)CC>>COC(=O)C1CC2=CC=C(C=C2C1)Br | O=[C:6]1[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:14][c:13]2[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12]2>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]2[CH2:14]1 | COC(=O)C1Cc2cc(Br)ccc2C1=O | COC(=O)C1Cc2ccc(Br)cc2C1 | null | null | C(=O)(C(F)(F)F)O | Reduction | OtherReaction | 6a1c34e1ccacafe0bd80d1f5ae97146d791a381b1dfbf61349064f8e4b70bdd9 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc2c(c1)CCC2 | O=[C;H0;D3;+0:1]1-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C:7]-[c:8]:[c:9]-1:[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]1-[C:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:1]-1 | null | [] | null | null | 18 | HOUR | Use of 5-bromo-indan-1-one (Intermediate NINETEEN-1) in a reaction with NaH and dimethylcarbonate (refer to procedures in Method EIGHTEEN) produced 5-bromo-1-oxo-indan-2-carboxylic acid methyl ester (Intermediate NINETEEN-2). A solution of 5-bromo-1-oxo-indan-2-carboxylic acid methyl ester (4.75 g, 17.7 mmol) in TFA (8... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | C(=O)(C(F)(F)F)O | null | 18 | COC(=O)C1Cc2cc(Br)ccc2C1=O>C(=O)(C(F)(F)F)O>COC(=O)C1Cc2ccc(Br)cc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-467a0d7965df4e4793d80e95c83d1100 | COC(=O)C1Cc2ccc(Br)cc2C1>>O=C(O)C1Cc2ccc(Br)cc2C1 | COC(=O)C1CC2=CC=C(C=C2C1)Br>>BrC=1C=C2CC(CC2=CC1)C(=O)O | C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[CH2:13]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[CH2:13]1 | COC(=O)C1Cc2ccc(Br)cc2C1 | O=C(O)C1Cc2ccc(Br)cc2C1 | null | null | CC(=O)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)CCC2 | 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 | null | null | Use of 5-bromo-indan-1-one (Intermediate NINETEEN-1) in a reaction with NaH and dimethylcarbonate (refer to procedures in Method EIGHTEEN) produced 5-bromo-1-oxo-indan-2-carboxylic acid methyl ester (Intermediate NINETEEN-2). A solution of 5-bromo-1-oxo-indan-2-carboxylic acid methyl ester (4.75 g, 17.7 mmol) in TFA (8... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)CCC2 | Other | CC(=O)O | null | null | COC(=O)C1Cc2ccc(Br)cc2C1>CC(=O)O>O=C(O)C1Cc2ccc(Br)cc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39187aa04b4741c7af65c404933627df | O=C(O)CCc1ccccc1Br>>O=C1CCc2c(Br)cccc21 | [Al+3].[Cl-].[Cl-].[Cl-].BrC1=C(C=CC=C1)CCC(=O)O.C(C(=O)Cl)(=O)Cl>>BrC1=C2CCC(C2=CC=C1)=O | O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]21 | O=C(O)CCc1ccccc1Br | O=C1CCc2c(Br)cccc21 | null | CN(C)C=O | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5fa70460ed4c9b149f869ba1e1d7456e1bbb70fa33dd43785c52e9f0686f4e57 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1CCc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7]-1:[c:8]:[c:9] | null | [] | 0 | CELSIUS | null | null | 4-Bromo-indan-1-one was obtained by the following procedure: A solution of 3-(2-bromo-phenyl)-propionic acid (commercially available from Oakwood Products) (15.0 g, 65.5 mmol) in CH2Cl2 at 0° C. was reacted with oxalyl chloride (7.2 mL, 1.5 eq) followed by 2–3 drops of DMF. The mixture was stirred until no more gas evo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | CN(C)C=O.C(Cl)Cl | 0 | null | O=C(O)CCc1ccccc1Br>CN(C)C=O.C(Cl)Cl>O=C1CCc2c(Br)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37f646d79a3c49df86a5c25e5f201708 | Cc1c(Cl)cccc1C(=O)O>>Cc1c(Cl)ccc2c1C(=O)CC2 | [Al+3].[Cl-].[Cl-].[Cl-].S(=O)(Cl)Cl.ClC=1C(=C(C(=O)O)C=CC1)C.C1=CC=CC=C1>>ClC1=CC=C2CCC(C2=C1C)=O | O[C:9]([c:8]1[c:2]([CH3:1])[c:3]([Cl:4])[cH:5][cH:6][cH:7]1)=[O:10]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[CH2:11][CH2:12]2 | Cc1c(Cl)cccc1C(=O)O | Cc1c(Cl)ccc2c1C(=O)CC2 | null | null | ClC(C)Cl | Functional Group Interconversion | OtherReaction | 5fa70460ed4c9b149f869ba1e1d7456e1bbb70fa33dd43785c52e9f0686f4e57 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1CCc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:8]-[C:9]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3]-1:[c:4] | 72 | [{"value": 72.0, "product": "ClC1=CC=C2CCC(C2=C1C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Thionyl chloride (10.0 mL, 1.5 eq) and 3-chloro-2-methyl-benzoic acid (commercially available from Aldrich) (15.6 g, 91.4 mmol) in benzene was refluxed until no more gas evolution was observed. After cooling to rt the mixture was concentrated. The concentrate was diluted with dichloroethane and added to a solution of A... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | ClC(C)Cl | null | 8 | Cc1c(Cl)cccc1C(=O)O>ClC(C)Cl>Cc1c(Cl)ccc2c1C(=O)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-395b0b58d94d4e89ade806c738c584d6 | O=C(O)c1cccc(Cl)c1Cl>>O=C1CCc2ccc(Cl)c(Cl)c21 | [Al+3].[Cl-].[Cl-].[Cl-].S(=O)(Cl)Cl.ClC1=C(C(=O)O)C=CC=C1Cl.C1=CC=CC=C1>>ClC1=CC=C2CCC(C2=C1Cl)=O | O[C:2](=[O:1])[c:12]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[c:10]1[Cl:11]>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[c:12]21 | O=C(O)c1cccc(Cl)c1Cl | O=C1CCc2ccc(Cl)c(Cl)c21 | null | null | ClC(C)Cl | Functional Group Interconversion | OtherReaction | 5fa70460ed4c9b149f869ba1e1d7456e1bbb70fa33dd43785c52e9f0686f4e57 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1CCc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:8]-[C:9]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3]-1:[c:4] | 80 | [{"value": 80.0, "product": "ClC1=CC=C2CCC(C2=C1Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Thionyl chloride (5.73 mL, ˜79 mmol) and 2,3-dichloro-benzoic acid (commercially available from Aldrich) (10.0 g, 52.4 mmol) in benzene was heated to reflux until no more gas evolution was observed. After cooling to rt the mixture was concentrated. The concentrate was diluted with dichloroethane and added to AlCl3 (7.0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | ClC(C)Cl | null | 8 | O=C(O)c1cccc(Cl)c1Cl>ClC(C)Cl>O=C1CCc2ccc(Cl)c(Cl)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63a36677e98d454d93144fbbcd713e23 | O=C(O)C=Cc1cccc(F)c1F>>O=C(O)CCc1cccc(F)c1F | FC1=C(C=CC(=O)O)C=CC=C1F>>FC1=C(C=CC=C1F)CCC(=O)O | [O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[c:12]1[F:13]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[c:12]1[F:13] | O=C(O)C=Cc1cccc(F)c1F | O=C(O)CCc1cccc(F)c1F | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | A solution of 2,3-difluorocinnamic acid (2.8 g, 15.2 mol) (commercially available from Lancaster) (Intermediate TWENTY-1) in ethanol (100 mL) was hydrogenated with H2 (balloon) and 10% Pd/C (0.3 g) at rt for 16 h. The mixture was filtered through Celite® and the solvent was evaporated to give 3-(2,3-difluoro-phenyl)-pr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | [Pd].C(C)O | null | null | O=C(O)C=Cc1cccc(F)c1F>[Pd].C(C)O>O=C(O)CCc1cccc(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e890937625b4be5ae684bf8922e4ae5 | O=C(O)CCc1cccc(F)c1F>>O=C1CCc2c1ccc(F)c2F | [Al+3].[Cl-].[Cl-].[Cl-].FC1=C(C=CC=C1F)CCC(=O)O.C(C(=O)Cl)(=O)Cl>>FC1=C2CCC(C2=CC=C1F)=O | O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[c:11]1[F:12]>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]2[F:12] | O=C(O)CCc1cccc(F)c1F | O=C1CCc2c1ccc(F)c2F | null | CN(C)C=O | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5fa70460ed4c9b149f869ba1e1d7456e1bbb70fa33dd43785c52e9f0686f4e57 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1CCc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7]-1:[c:8]:[c:9] | null | [] | null | null | 2 | HOUR | A solution of 2,3-difluorocinnamic acid (2.8 g, 15.2 mol) (commercially available from Lancaster) (Intermediate TWENTY-1) in ethanol (100 mL) was hydrogenated with H2 (balloon) and 10% Pd/C (0.3 g) at rt for 16 h. The mixture was filtered through Celite® and the solvent was evaporated to give 3-(2,3-difluoro-phenyl)-pr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | CN(C)C=O.C(Cl)Cl | null | 2 | O=C(O)CCc1cccc(F)c1F>CN(C)C=O.C(Cl)Cl>O=C1CCc2c1ccc(F)c2F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bd0f005d77a4fd481fc55c63a23a3a2 | CCOC(=O)CC1CCc2c1ccc(F)c2F>>OCCC1CCc2c1ccc(F)c2F | C(C)OC(CC1CCC2=C(C(=CC=C12)F)F)=O.[Li+].[BH4-]>>FC1=C2CCC(C2=CC=C1F)CCO | CCO[C:2](=[O:1])[CH2:3][CH:4]1[CH2:5][CH2:6][c:7]2[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]2[F:14]>>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][c:7]2[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]2[F:14] | CCOC(=O)CC1CCc2c1ccc(F)c2F | OCCC1CCc2c1ccc(F)c2F | null | [Pd] | CO.C1CCOC1.CCOC(=O)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2c(c1)CCC2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | A mixture of E- and Z-(4,5-difluoro-indan-1-ylidene)-acetic acid ethyl ester (Intermediate TWENTY-3) (1.1 g) in EtOAc (25 mL) was hydrogenated with 10% Pd/C (0.16 g) under H2 (balloon) at rt for 16 h. The mixture was filtered through a bed of Celite® and the filtrate was evaporated under vacuum. The ester, (4,5-difluor... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2c(c1)CCC2 | HO- | [Pd].CO.C1CCOC1.CCOC(=O)C | null | null | CCOC(=O)CC1CCc2c1ccc(F)c2F>[Pd].CO.C1CCOC1.CCOC(=O)C>OCCC1CCc2c1ccc(F)c2F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b9de1057bbe403baed0bb47fffa7c28 | O=C1c2cccnc2CCC1Cc1c[nH]cn1>>c1cnc2c(c1)CC(Cc1c[nH]cn1)CC2 | [OH-].[K+].N1C=NC(=C1)CC1C(C=2C=CC=NC2CC1)=O.NN>>N1C=NC(=C1)CC1CC=2C=CC=NC2CC1 | O=[C:7]1[c:5]2[c:4]([n:3][cH:2][cH:1][cH:6]2)[CH2:16][CH2:15][CH:8]1[CH2:9][c:10]1[cH:11][nH:12][cH:13][n:14]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH:8]([CH2:9][c:10]1[cH:11][nH:12][cH:13][n:14]1)[CH2:15][CH2:16]2 | O=C1c2cccnc2CCC1Cc1c[nH]cn1 | c1cnc2c(c1)CC(Cc1c[nH]cn1)CC2 | null | null | C(=O)(O)[O-].[Na+].O.C(COCCO)O | Reduction | OtherReaction | c75925b35ee2d5552de19b47813876b5230d4b373c49e7a684e043aaa1cea5d6 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1cnc2c(c1)CC(Cc1c[nH]cn1)CC2 | O=[C;H0;D3;+0:1]1-[C:2](-[C:3])-[C:4]-[C:5]-[c:6](:[#7;a:7]:[c:8]):[c:9]-1:[c:10]>>[C:3]-[C:2]1-[C:4]-[C:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](:[c:10])-[CH2;D2;+0:1]-1 | null | [] | 170 | CELSIUS | null | null | Use of 7,8-dihydro-6H-quinolin-5-one (Intermediate TWENTYTWO-1) (obtained as described in Molina, et. al. Tetrahedron 1995, 51, 1265, incorporated herein by reference) in Method E produced 6-(1H-imidazol-4-ylmethyl)-7,8-dihydro-6H-quinolin-5-one (Intermediate TWENTYTWO-2). To a solution of 6-(1H-imidazol-4-ylmethyl)-7,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2.c1c[nH]cn1 | Other | C(=O)(O)[O-].[Na+].O.C(COCCO)O | 170 | null | O=C1c2cccnc2CCC1Cc1c[nH]cn1>C(=O)(O)[O-].[Na+].O.C(COCCO)O>c1cnc2c(c1)CC(Cc1c[nH]cn1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c0c6bf75b19483c82a57fcb9c08452e | CCOC(C)=O.O=C1CCc2c(Cl)cccc21>>CCOC(=O)CC1CCc2c(Cl)cccc21 | [H-].[Na+].ClC1=C2CCC(C2=CC=C1)=O.CCOC(=O)C>>C(C)OC(CC1CCC2=C(C=CC=C12)Cl)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].O=[C:7]1[CH2:8][CH2:9][c:10]2[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][c:10]2[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]21 | CCOC(C)=O.O=C1CCc2c(Cl)cccc21 | CCOC(=O)CC1CCc2c(Cl)cccc21 | null | [Rh] | C1CCOC1 | C-C Coupling | OtherReaction | 494b529c4b01bb0dca388321e034d6f4fb2fd91ad19b78524aceef0167199e0d | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | c1ccc2c(c1)CCC2 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6].[C:7]-[#8:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:11])-[CH2;D2;+0:10]-[CH;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6] | null | [] | null | null | 16 | HOUR | Use of 2-chlorocinnamic acid (Intermediate TWENTYTHREE-1) (commercially available from Aldrich) in the applicable process steps described in Method TWENTY produced 4-chloro-indan-1-one (Intermediate TWENTYFOUR-1). Triethylphosphonoacetate (3.5 mL, 17.2 mmol) was added to a mixture of NaH (0.69 g, 12.2 mmol) in THF (25 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | [Rh].C1CCOC1 | null | 16 | CCOC(C)=O.O=C1CCc2c(Cl)cccc21>[Rh].C1CCOC1>CCOC(=O)CC1CCc2c(Cl)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bd5b34b9668455190055c5e0f263011 | O=C1CCc2c(Br)cccc21.S=c1[nH]cc(C2Cc3cccc(Br)c3C2)[nH]1>>S=c1[nH]cc(CC2CCc3c(Br)cccc32)[nH]1 | BrC1=C2CCC(C2=CC=C1)=O.BrC1=C2CC(CC2=CC=C1)C=1NC(NC1)=S>>BrC1=C2CCC(C2=CC=C1)CC=1NC(NC1)=S | O=[C:7]1[CH2:8][CH2:9][c:10]2[c:11]([Br:12])[cH:13][cH:14][cH:15][c:16]21.Brc1cccc2c1C[CH:6]([c:5]1[cH:4][nH:3][c:2](=[S:1])[nH:17]1)C2>>[S:1]=[c:2]1[nH:3][cH:4][c:5]([CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([Br:12])[cH:13][cH:14][cH:15][c:16]32)[nH:17]1 | O=C1CCc2c(Br)cccc21.S=c1[nH]cc(C2Cc3cccc(Br)c3C2)[nH]1 | S=c1[nH]cc(CC2CCc3c(Br)cccc32)[nH]1 | null | null | null | C-C Coupling | OtherReaction | b7fea274054caafc7784f037120973a3c40d41ce02abedda9427ae073660400a | 554b1bee1ccf92984990164979ec7aaf354dc2a70796dc88c3036796633e99e1 | S=c1[nH]cc(CC2CCc3ccccc32)[nH]1 | Br-c1:c:c:c:c2:c:1-C-[CH;D3;+0:1](-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1)-C-2.O=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12]>>[c:12]:[c:11]1:[c:10]-[C:9]-[C:8]-[CH;D3;+0:7]-1-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | null | null | null | null | Use of 4-bromoindanone (obtained by the procedures in Example NINETEEN-1 (Compound 149) in Method TWENTYFOUR produced 4-(4-bromo-indan-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 167).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | null | c1ccc2c(c1)CCC2.c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1c[nH]cn1.c1ccc2c(c1)CCC2 | HBr | null | null | null | O=C1CCc2c(Br)cccc21.S=c1[nH]cc(C2Cc3cccc(Br)c3C2)[nH]1>>S=c1[nH]cc(CC2CCc3c(Br)cccc32)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6d569a98bd045b096ff8164515028c3 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1c2ccccc2CCC1Cc1c[nH]cn1>>O=C1c2ccccc2CCC1Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | N1C=NC(=C1)CC1C(C2=CC=CC=C2CC1)=O.N1C=NC(=C1)CC1C(C2=CC=CC=C2CC1)=O.C(C)N(CC)CC.C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1C=NC(=C1)CC1C(C2=CC=CC=C2CC1)=O | Cl[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)([c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1.[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][CH2:10][CH:11]1[CH2:12][c:13]1[cH:14][nH:15][cH:35][n:36]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][CH2:10... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1c2ccccc2CCC1Cc1c[nH]cn1 | O=C1c2ccccc2CCC1Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e11c706bbc4ed4c537e0a88a7bb26c47a17011e98b2e37f239a30e81d0496061 | 677f263b618a481bcdc02c85060e6c44b1f44f328207057cd4782b98754b7773 | O=C1c2ccccc2CCC1Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[C:11]-[c:12]1:[#7;a:13]:[c:14]:[nH;D2;+0:15]:[c:16]:1>>[C:11]-[c:12]1:[#7;a:13]:[c:14]:[n;H0;D3;+0:15](-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10]):[c:16]:1 | null | [] | null | null | null | null | A solution of 2-(1H-imidazol-4-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one (Intermediate E4) (2.11 g, 9.3 mmol) in DMF (25 mL) was treated with triethyl amine (1.9 mL, 13.6 mmol) and triphenylmethylchloride (tritylchloride) (2.74 g, 9.6 mmol, added dropwise in DMF (25 mL)). After 16 h at rt the mixture was partitioned be... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccc2c(c1)CCCC2.c1c[nH]cn1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | null | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1c2ccccc2CCC1Cc1c[nH]cn1>CN(C)C=O>O=C1c2ccccc2CCC1Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-092c15c54f9544a98141d68f8848fcc2 | CCOP(=O)(CC#N)OCC.O=C1c2ccccc2CCC1Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1>>N#CC=C1c2ccccc2CCC1Cc1c[nH]cn1 | [H-].[Na+].C(C)OP(OCC)(=O)CC#N.[H-].[Na+].C(C)OP(OCC)(=O)CC#N.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1C=NC(=C1)CC1C(C2=CC=CC=C2CC1)=O>>N1C=NC(=C1)CC1C(C2=CC=CC=C2CC1)=CC#N | CCOP(=O)(OCC)[CH2:3][C:2]#[N:1].O=[C:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][CH2:12][CH:13]1[CH2:14][c:15]1[cH:16][n:17](C(c2ccccc2)(c2ccccc2)c2ccccc2)[cH:18][n:19]1>>[N:1]#[C:2][CH:3]=[C:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][CH2:12][CH:13]1[CH2:14][c:15]1[cH:16][nH:17][cH:18][n:19]1 | CCOP(=O)(CC#N)OCC.O=C1c2ccccc2CCC1Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | N#CC=C1c2ccccc2CCC1Cc1c[nH]cn1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 47bf1c3aedd17a317c1f93fa6525c8e2e2ed528867ea5276a8a3dfc10d423ae4 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | [CH]=C1c2ccccc2CCC1Cc1c[nH]cn1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].O=[C;H0;D3;+0:4](-[C:5](-[C:6]-[c:7]1:[#7;a:8]:[c:9]:[n;H0;D3;+0:10](-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):[c:11]:1)-[C:12])-[c:13](:[c:14]):[c:15]>>[C:12]-[C:5](-[C:6]-[c:7]1:[#7;a:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1)-[C;H0;D3;+0:4](=[CH;D2;+0:1]-[C:2]#[N;... | null | [] | null | null | 16 | HOUR | A solution of 2-(1H-imidazol-4-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one (Intermediate E4) (2.11 g, 9.3 mmol) in DMF (25 mL) was treated with triethyl amine (1.9 mL, 13.6 mmol) and triphenylmethylchloride (tritylchloride) (2.74 g, 9.6 mmol, added dropwise in DMF (25 mL)). After 16 h at rt the mixture was partitioned be... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCCC2.c1c[nH]cn1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCCC2.c1c[nH]cn1 | c1ccc2c(c1)CCCC2.c1c[nH]cn1 | HO- | CN(C)C=O | null | 16 | CCOP(=O)(CC#N)OCC.O=C1c2ccccc2CCC1Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1>CN(C)C=O>N#CC=C1c2ccccc2CCC1Cc1c[nH]cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-099d9a9db3364adcb35165d5d1ed609e | O=C(Cl)Oc1ccccc1.c1nc(CC2CCC3=C2CCC3)c[nH]1>>O=c1[nH]cc(CC2CCC3=C2CCC3)[nH]1 | ClC(=O)OC1=CC=CC=C1.C1(CCC=2CCCC12)CC=1N=CNC1.C(=O)(O)[O-].[Na+]>>C1(CCC=2CCCC12)CC=1NC(NC1)=O | ClC(Oc1ccccc1)=[O:1].[cH:2]1[nH:3][cH:4][c:5]([CH2:6][CH:7]2[CH2:8][CH2:9][C:10]3=[C:11]2[CH2:12][CH2:13][CH2:14]3)[n:15]1>>[O:1]=[c:2]1[nH:3][cH:4][c:5]([CH2:6][CH:7]2[CH2:8][CH2:9][C:10]3=[C:11]2[CH2:12][CH2:13][CH2:14]3)[nH:15]1 | O=C(Cl)Oc1ccccc1.c1nc(CC2CCC3=C2CCC3)c[nH]1 | O=c1[nH]cc(CC2CCC3=C2CCC3)[nH]1 | null | null | C1CCOC1.O | Miscellaneous | OtherReaction | 82d419be310f94e0fb372475936a7f6ca5545d4fb6630b253bc6e6c76775fdd0 | 11873959194d43f291af7fba282284829cc9317bd0f9101d9a22013c97d9b731 | O=c1[nH]cc(CC2CCC3=C2CCC3)[nH]1 | Cl-C(=[O;H0;D1;+0:1])-O-c1:c:c:c:c:c:1.[C:2]-[c:3]1:[c:4]:[#7;a:5]:[cH;D2;+0:6]:[n;H0;D2;+0:7]:1>>[C:2]-[c:3]1:[c:4]:[#7;a:5]:[c;H0;D3;+0:6](=[O;H0;D1;+0:1]):[nH;D2;+0:7]:1 | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-(1,2,3,4,5,6-hexahydro-pentalen-1-ylmethyl)-1H-imidazole; fumarate salt (Intermediate A5 as described in Example A, 340 mg, 1.81 mmol) in THF (15 mL) and water (15 mL) was treated with NaHCO3 (1.52 g, 18 mmol) at rt for 30 m. Phenyl chloroformate (600 mL, 4.7 mmol) was added and stirring was continued f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | null | c1ccccc1.c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.C1CC2=C(C1)CCC2 | HCl | C1CCOC1.O | null | 1 | O=C(Cl)Oc1ccccc1.c1nc(CC2CCC3=C2CCC3)c[nH]1>C1CCOC1.O>O=c1[nH]cc(CC2CCC3=C2CCC3)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3d9b7426dec42f29bec9b8563dce9bd | c1ccc(COCCC2CCC3(CC2)OCCO3)cc1>>O=C1CCC(CCOCc2ccccc2)CC1 | C(C1=CC=CC=C1)OCCC1CCC2(OCCO2)CC1.O.CC=1C=CC(=CC1)S(=O)(=O)O>>C(C1=CC=CC=C1)OCCC1CCC(CC1)=O | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[CH2:16][CH2:17]2>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | c1ccc(COCCC2CCC3(CC2)OCCO3)cc1 | O=C1CCC(CCOCc2ccccc2)CC1 | null | null | CC(=O)C | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCC(CCOCc2ccccc2)CC1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | 97 | [{"value": 97.0, "product": "C(C1=CC=CC=C1)OCCC1CCC(CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-(2-Benzyloxy-ethyl)-1,4-dioxa-spiro[4.5]decane (Intermediate R1, 1.02 g, 3.70 mmol) (obtainable as described in the publication by Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016, incorporated herein by reference) was dissolved in acetone (100 mL): H2O (5 mL) and reacted with TsOH (140 mg, 0.74 mmol) at 45° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | CC(=O)C | null | null | c1ccc(COCCC2CCC3(CC2)OCCO3)cc1>CC(=O)C>O=C1CCC(CCOCc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36c0fb0cef9b4fd690399403bca865cf | COC(=O)C#N.O=C1CCC(CCOCc2ccccc2)CC1>>COC(=O)C1CC(CCOCc2ccccc2)CCC1=O | C(#N)C(=O)OC.CN(C)P(=O)(N(C)C)N(C)C.[Li+].CC(C)[N-]C(C)C.C(C1=CC=CC=C1)OCCC1CCC(CC1)=O>>COC(=O)C1C(CCC(C1)CCOCC1=CC=CC=C1)=O | N#C[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][CH:7]([CH2:8][CH2:9][O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19][C:20]1=[O:21]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([CH2:8][CH2:9][O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19][C:20]1=[O:21] | COC(=O)C#N.O=C1CCC(CCOCc2ccccc2)CC1 | COC(=O)C1CC(CCOCc2ccccc2)CCC1=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 6a637de02d731d3d400000ea4c333bde9eb2fe719003381bc70d0bd8f95d6bee | ea62efa90ef3cfb13125a23e62e9e1787aa2a0b0ee48c8a61b3326a3bda24134 | O=C1CCC(CCOCc2ccccc2)CC1 | N#C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9]-[C:10]>>[C:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4])-[C:9]-[C:10] | null | [] | 0 | CELSIUS | null | null | A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 m before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added and the mixture was stirred for 15 m ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Ketone.Ester | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | Other | C1CCOC1 | 0 | null | COC(=O)C#N.O=C1CCC(CCOCc2ccccc2)CC1>C1CCOC1>COC(=O)C1CC(CCOCc2ccccc2)CCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a212ef8076d6461486f10c4b5443e7f8 | COC(=O)C1CC(CCOCc2ccccc2)CCC1O>>COC(=O)C1=CCCC(CCOCc2ccccc2)C1 | C1CCC2=NCCCN2CC1.CCOC(=O)C.COC(=O)C1C(CCC(C1)CCOCC1=CC=CC=C1)O.O=S(Cl)Cl>>COC(=O)C1=CCCC(C1)CCOCC1=CC=CC=C1 | O[CH:6]1[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:20][CH:9]([CH2:10][CH2:11][O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:8][CH2:7]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[CH:6][CH2:7][CH2:8][CH:9]([CH2:10][CH2:11][O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20]1 | COC(=O)C1CC(CCOCc2ccccc2)CCC1O | COC(=O)C1=CCCC(CCOCc2ccccc2)C1 | null | null | N1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 579eaa370a2e820e4e797509751f1a267c4c2023a9c84c83636e14e9358f50f3 | 41a0f24bab2dd1842411d86540b9e431e13b91d9b083780e582360bedf475320 | C1=CCC(CCOCc2ccccc2)CC1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-[CH;D3;+0:6]-1-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]>>[C;D1;H3:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:6]1=[CH;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5]-1 | null | [] | 55 | CELSIUS | null | null | A solution of 5-(2-benzyloxy-ethyl)-2-hydroxy-cyclohexanecarboxylic acid methyl ester (Intermediate R2, 0.72 g, 2.48 mmol) in pyridine (10 mL) was treated with SOCl2 (0.73 mL, 12.4 mmol) at −20° C. The mixture was allowed to react for 15 m and was then warmed to 55° C. for 16 h. The solvents were removed under vacuum a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Ester | C1CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HO- | N1=CC=CC=C1 | 55 | null | COC(=O)C1CC(CCOCc2ccccc2)CCC1O>N1=CC=CC=C1>COC(=O)C1=CCCC(CCOCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02c6ad70fe5f4ce699d15439da78968c | COC(=O)C1=CCCC(CCOCc2ccccc2)C1>>CC1=CCCC(CCOCc2ccccc2)C1 | COC(=O)C1=CCCC(C1)CCOCC1=CC=CC=C1.CC(C)C[AlH]CC(C)C.N1=CC=CC=C1.S(=O)(=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC=1CC(CCC1)CCOCC1=CC=CC=C1 | CO[C:1](=O)[C:2]1=[CH:3][CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1>>[CH3:1][C:2]1=[CH:3][CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1 | COC(=O)C1=CCCC(CCOCc2ccccc2)C1 | CC1=CCCC(CCOCc2ccccc2)C1 | null | null | C1CCOC1 | Reduction | OtherReaction | bbe4aa74424ca2aa68ccc284976164429303e3793b330c9b63e6e77a951d8d58 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | C1=CCC(CCOCc2ccccc2)CC1 | C-O-[C;H0;D3;+0:1](=O)-[C:2](=[C:3]-[C:4])-[C:5]>>[C:5]-[C:2](-[CH3;D1;+0:1])=[C:3]-[C:4] | 82 | [{"value": 82.0, "product": "CC=1CC(CCC1)CCOCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-(2-Benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester (Intermediate R3 obtained above in Example R1 in accordance with Method R) was reduced with DIBAL. The resulting alcohol (Intermediate R7, 1.18 g, 4.81 mmol) in THF (20 mL) at 0° C. was treated with sulfur trioxide-pyridine. (1.15 g, 7.21 mmol) for 3 h. L... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | C1=CCCCC1.c1ccccc1 | Other | C1CCOC1 | null | 3 | COC(=O)C1=CCCC(CCOCc2ccccc2)C1>C1CCOC1>CC1=CCCC(CCOCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-470e70b40dd84612b6776db3961162df | CC(C)[Si](OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C.O=C1CCC(CCO)CC1>>CC(C)[Si](OCCC1CCC(=O)CC1)(C(C)C)C(C)C | OCCC1CCC(CC1)=O.C(C)(C)N(CC)C(C)C.FC(S(=O)(=O)O[Si](C(C)C)(C(C)C)C(C)C)(F)F>>C(C)(C)[Si](OCCC1CCC(CC1)=O)(C(C)C)C(C)C | O=S(=O)(O[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20])C(F)(F)F.[OH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH2:14]1>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH2:14]1)([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:... | CC(C)[Si](OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C.O=C1CCC(CCO)CC1 | CC(C)[Si](OCCC1CCC(=O)CC1)(C(C)C)C(C)C | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 1e32bf15362f1db6caa13aeae0e4a2332995f251d0e7d3892b6ae595fa4cebef | 6deb768ca6c69e1952bf0a14ab712bbae796f6fbf3723f779ccbc0662be93df5 | O=C1CCCCC1 | F-C(-F)(-F)-S(=O)(=O)-O-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[C:11]-[C:12]-[OH;D1;+0:13]>>[C:11]-[C:12]-[O;H0;D2;+0:13]-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10] | null | [] | 0 | CELSIUS | null | null | A solution of 4-(2-hydroxy-ethyl)-cyclohexanone (Intermediate R10, 6.8 g, 52.6 mmol, (obtainable as described in the publication by Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016) was dissolved in CH2Cl2 (75 mL) and treated with diisopropylethylamine (9.2 mL, 52.6 mmol) followed by tri-isopropylsilyl trifluorome... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary alcohol.Silyl protective group | Silyl protective group | null | null | C1CCCCC1 | TfOH.HO- | C(Cl)Cl | 0 | null | CC(C)[Si](OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C.O=C1CCC(CCO)CC1>C(Cl)Cl>CC(C)[Si](OCCC1CCC(=O)CC1)(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ddb018270b74e6f9303a922edff502b | CC(C)[Si](OCCC1CCC=C(C=O)C1)(C(C)C)C(C)C.C[Si](C)(C)C=[N+]=[N-]>>C#CC1=CCCC(CCO[Si](C(C)C)(C(C)C)C(C)C)C1 | C(C)(C)[Si](OCCC1CCC=C(C1)C=O)(C(C)C)C(C)C.[Si](C)(C)(C)C=[N+]=[N-].[Li]CCCC>>C(#C)C=1CC(CCC1)CCO[Si](C(C)C)(C(C)C)C(C)C | O=[CH:2][C:3]1=[CH:4][CH2:5][CH2:6][CH:7]([CH2:8][CH2:9][O:10][Si:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20])[CH2:21]1.C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH:1]#[C:2][C:3]1=[CH:4][CH2:5][CH2:6][CH:7]([CH2:8][CH2:9][O:10][Si:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:16])[CH3:17])[CH:1... | CC(C)[Si](OCCC1CCC=C(C=O)C1)(C(C)C)C(C)C.C[Si](C)(C)C=[N+]=[N-] | C#CC1=CCCC(CCO[Si](C(C)C)(C(C)C)C(C)C)C1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | b4c50d40bd73f29fc59705faabbc29885d48952a3cd07fd1e79a6158348af59e | 1cf50b336c146b01b0780412724e40fc1414b82a1d6078fe921f14b132744e18 | C1=CCCCC1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].O=[CH;D2;+0:2]-[C:3](=[C:4]-[C:5])-[C:6]>>[C:6]-[C:3](-[C;H0;D2;+0:2]#[CH;D1;+0:1])=[C:4]-[C:5] | null | [] | null | null | null | null | A solution of TMS-diazomethane (4.61 mL, 9.22 mmol) in THF (60 mL) was reacted with n-BuLi (5.0 mL, 7.99 mmol) at −78° C. for 0.5 h. 5-(2-triisopropylsilanyloxy-ethyl)-cyclohex-1-enecarbaldehyde (Intermediate R13) was added via cannula. The mixture was reacted at −78° C. for 1 h and at 0° C. for 1 h. After work-up and ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Diazo.Silyl protective group | Alkyne | null | null | C1=CCCCC1 | HO- | C1CCOC1 | null | null | CC(C)[Si](OCCC1CCC=C(C=O)C1)(C(C)C)C(C)C.C[Si](C)(C)C=[N+]=[N-]>C1CCOC1>C#CC1=CCCC(CCO[Si](C(C)C)(C(C)C)C(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-694fed7805bc4205a8b843e02f34766d | C=CC1=CCCC(Cc2c[nH]cn2)C1.OO>>CCC1=CCCC(Cc2c[nH]c(=O)[nH]2)C1 | OO.C(=C)C=1CC(CCC1)CC=1N=CNC1.NN.O>>C(C)C=1CC(CCC1)CC=1NC(NC1)=O | [CH2:1]=[CH:2][C:3]1=[CH:4][CH2:5][CH2:6][CH:7]([CH2:8][c:9]2[cH:10][nH:11][cH:12][n:14]2)[CH2:15]1.O[OH:13]>>[CH3:1][CH2:2][C:3]1=[CH:4][CH2:5][CH2:6][CH:7]([CH2:8][c:9]2[cH:10][nH:11][c:12](=[O:13])[nH:14]2)[CH2:15]1 | C=CC1=CCCC(Cc2c[nH]cn2)C1.OO | CCC1=CCCC(Cc2c[nH]c(=O)[nH]2)C1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 60747b62e45636256388d4dafb4e1c1823ad34aea5db13df35593c9678c13d9d | f31c628702cf0fcf5a903442a4ec25cb67ad0ae56b375a9a0f274c0dccf17a1c | O=c1[nH]cc(CC2CC=CCC2)[nH]1 | O-[OH;D1;+0:1].[C:2]-[C:3](-[CH;D2;+0:4]=[CH2;D1;+0:5])=[C:6]-[C:7].[C:8]-[c:9]1:[c:10]:[#7;a:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:1>>[C:2]-[C:3](-[CH2;D2;+0:4]-[CH3;D1;+0:5])=[C:6]-[C:7].[C:8]-[c:9]1:[c:10]:[#7;a:11]:[c;H0;D3;+0:12](=[O;H0;D1;+0:1]):[nH;D2;+0:13]:1 | null | [] | 0 | CELSIUS | 6 | HOUR | A mixture of NiCl2 (0.364 g, 2.81 mmol) in EtOH (20 mL) was reacted with NaBH4 (0.053 mg, 1.40 mmol) at rt for 15 m after saturation of the solution with hydrogen gas. Ethylene diamine (0.17 g, 2.81 mmol) was added followed by the alkynyl imidazol (Intermediate R15, 0.26 g, 1.40 mmol) at rt for 45 m under an atmosphere... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Vinyl | null | c1c[nH]cn1 | c1c[nH]cn1 | C1=CCCCC1.c1c[nH]cn1 | Other | C(C)O | 0 | 6 | C=CC1=CCCC(Cc2c[nH]cn2)C1.OO>C(C)O>CCC1=CCCC(Cc2c[nH]c(=O)[nH]2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd97467992de4fa6b98437d8bbc8d45d | O=C(O)C1CCc2cc(F)ccc21>>O=C(O)[C@@H]1CCc2cc(F)ccc21 | COC=1C=C2C(=CC1OC)N3[C@@H]4[C@]25CCN6[C@H]5C[C@@H]7[C@H]4[C@H](CC3=O)OCC=C7C6.FC=1C=C2CCC(C2=CC1)C(=O)O.FC=1C=C2CCC(C2=CC1)C(=O)O.FC=1C=C2CCC(C2=CC1)C(=O)O.Cl>>FC=1C=C2CC[C@H](C2=CC1)C(=O)O | [O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]21>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]21 | O=C(O)C1CCc2cc(F)ccc21 | O=C(O)[C@@H]1CCc2cc(F)ccc21 | null | null | CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(c1)CCC2 | null | 10.5 | [{"value": 10.5, "product": "FC=1C=C2CC[C@H](C2=CC1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The combined mother liquors from the resolution of Intermediate T3 were concentrated under reduced pressure until no acetone remained and acidified to pH 3 with 0° C. 5N HCl. This solution was extracted 3 times with Et2O (200 ml portions) and the combined Et2O portions were washed successively with 1N HCl, H2O and brin... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)CCC2 | null | CC(=O)C | null | null | O=C(O)C1CCc2cc(F)ccc21>CC(=O)C>O=C(O)[C@@H]1CCc2cc(F)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfaeb299ce614cc1b00cd1c3898b5524 | CC1=C(Br)C(O)CC1>>CCC1=C(C)CCC1O | BrC=1C(CCC1C)O.C(C)[Mg]Br>>C(C)C=1C(CCC1C)O | Br[C:3]1=[C:4]([CH3:5])[CH2:6][CH2:7][CH:8]1[OH:9]>>[CH3:1][CH2:2][C:3]1=[C:4]([CH3:5])[CH2:6][CH2:7][CH:8]1[OH:9] | CC1=C(Br)C(O)CC1 | CCC1=C(C)CCC1O | null | [Ni](Cl)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1 | Functional Group Interconversion | OtherReaction | a82332ed27065c9fa7794673a8ff03debc03a422dc5d86bfdfdaf348f60818d9 | ec7c8e18578a00f3028f55e642ee15a34a79a79f174afac37d3207d26250efd7 | C1=CCCC1 | Br-[C;H0;D3;+0:1]1=[C:2](-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-1-[O;D1;H1:7]>>[C;D1;H3:8]-[C:9]-[C;H0;D3;+0:1]1=[C:2](-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-1-[O;D1;H1:7] | null | [] | null | null | null | null | The alcohol (Intermediate V2, 16 mmol) in THF (30 mL) at 0° C. was treated with ethyl magnesium bromide (40 mmol). The catalyst, 1,3-bis(diphenylphosphino)propane nickel (11) chloride (0.75 mmol) (NiCl2dppp) was added in one portion and the mixture was heated to reflux for 3 hours following the procedure of Organ et al... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Br- | [Ni](Cl)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1 | null | null | CC1=C(Br)C(O)CC1>[Ni](Cl)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>CCC1=C(C)CCC1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edb19e9ecf824c87ace7643d36df2462 | C=CCc1ccc2c(c1)OCO2>>CC=Cc1ccc2c(c1)OCO2 | O1COC2=CC(CC=C)=CC=C12.[OH-].[K+].Cl>>O1COC2=CC(C=CC)=CC=C12 | [CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][O:12]2>>[CH3:1][CH:2]=[CH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][O:12]2 | C=CCc1ccc2c(c1)OCO2 | CC=Cc1ccc2c(c1)OCO2 | null | null | C(CCC)O | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | c1ccc2c(c1)OCO2 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[CH3;D1;+0:1]-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 98,652.6 | [{"value": 97.0, "product": "O1COC2=CC(C=CC)=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98652.6, "product": "O1COC2=CC(C=CC)=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Synthesis of isosafrale To 80 g (0.49 mmol) of safrole was added 100 ml of a 3N solution of potassium hydroxide (KOH) in n-butyl alcohol and the reaction mixture was stirred at room temperature for 3 h. The mixture was poured into a solution of 12 ml of concentrated hydrochloric acid (HCl), and 52 ml of ice water. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | c1ccc2c(c1)OCO2 | null | C(CCC)O | null | 3 | C=CCc1ccc2c(c1)OCO2>C(CCC)O>CC=Cc1ccc2c(c1)OCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-386fea515fe549098d963803cb3d34d0 | CC(C)(C)OC(=O)NCc1ccc(N)cc1.Cc1ccccc1N=C=O>>Cc1ccccc1NC(=O)Nc1ccc(CNC(=O)OC(C)(C)C)cc1 | CC1=C(C=CC=C1)N=C=O.C(C)(C)(C)OC(NCC1=CC=C(C=C1)N)=O>>CC1=C(C=CC=C1)NC(=O)NC1=CC=C(CNC(OC(C)(C)C)=O)C=C1 | [NH2:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]=[C:9]=[O:10]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][NH:17][C:18](=[O:19])[O:20]... | CC(C)(C)OC(=O)NCc1ccc(N)cc1.Cc1ccccc1N=C=O | Cc1ccccc1NC(=O)Nc1ccc(CNC(=O)OC(C)(C)C)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | 2-Methylphenylisocyanate (7.57 g, 59.83 mmol) was added dropwise at 0° C. to a solution of (4-amino-benzyl)-carbamic acid tert-butyl ester (13.30 g, 59.83 mmol, prepared analoguous to: Moloney, Gerard P.; Martin, Graeme R.; Mathews, Neil; Milne, Aynsley; Hobbs, Heather; et al. J Med. Chem. 1999, 42, 2504–2526) in 120 m... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)(C)OC(=O)NCc1ccc(N)cc1.Cc1ccccc1N=C=O>C(Cl)Cl>Cc1ccccc1NC(=O)Nc1ccc(CNC(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7df99201e2a45bfaa337e797e30760b | Cc1ccccc1NC(=O)Nc1ccc(CNC(=O)OC(C)(C)C)cc1>>Cc1ccccc1NC(=O)Nc1ccc(CN)cc1 | CC1=C(C=CC=C1)NC(=O)NC1=CC=C(CNC(OC(C)(C)C)=O)C=C1>>NCC1=CC=C(C=C1)NC(=O)NC1=C(C=CC=C1)C | CC(C)(C)OC(=O)[NH:17][CH2:16][c:15]1[cH:14][cH:13][c:12]([NH:11][C:9]([NH:8][c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:10])[cH:19][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][NH2:17])[cH:18][cH:19]1 | Cc1ccccc1NC(=O)Nc1ccc(CNC(=O)OC(C)(C)C)cc1 | Cc1ccccc1NC(=O)Nc1ccc(CN)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccccc1)Nc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | null | [] | null | null | 2 | HOUR | To a solution of tert-butyl 4-({[(2-methylphenyl)amino]carbonyl}amino)benzylcarbamate (2.00 g, 5.63 mmol) in CH2Cl2 (120 mL) TFA (36 mL) was added at 0° C. and stirred for 2 h at r.t.. The reaction mixture was evaporated and the product was collected (2.72 g, TFA salt). M.p. 142–143° C.; TLC (PE/EtOAc 3/2) Rf 0.14; 1H ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 2 | Cc1ccccc1NC(=O)Nc1ccc(CNC(=O)OC(C)(C)C)cc1>C(Cl)Cl>Cc1ccccc1NC(=O)Nc1ccc(CN)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8003c8aab514e7886d4813c31252eda | COc1ccc(C(CC(=O)Nc2ccc(NC(=O)Nc3ccccc3C)cc2)NC(=O)c2ccc(C(=O)OC(C)(C)C)cc2)cc1OC>>COc1ccc(C(CC(=O)Nc2ccc(NC(=O)Nc3ccccc3C)cc2)NC(=O)c2ccc(C(=O)O)cc2)cc1OC | C(C)(C)(C)OC(C1=CC=C(C=C1)C(=O)NC(CC(=O)NC1=CC=C(C=C1)NC(=O)NC1=C(C=CC=C1)C)C1=CC(=C(C=C1)OC)OC)=O.C(=O)(C(F)(F)F)O>>COC=1C=C(C=CC1OC)C(CC(=O)NC1=CC=C(C=C1)NC(=O)NC1=C(C=CC=C1)C)NC(=O)C1=CC=C(C(=O)O)C=C1 | CC(C)(C)[O:38][C:36]([c:35]1[cH:34][cH:33][c:32]([C:30]([NH:29][CH:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:42]([O:43][CH3:44])[cH:41]2)[CH2:8][C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[NH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[CH3:26])[cH:27][cH:28]2)=[O:31])[cH:40][cH:39]1)=[O:37... | COc1ccc(C(CC(=O)Nc2ccc(NC(=O)Nc3ccccc3C)cc2)NC(=O)c2ccc(C(=O)OC(C)(C)C)cc2)cc1OC | COc1ccc(C(CC(=O)Nc2ccc(NC(=O)Nc3ccccc3C)cc2)NC(=O)c2ccc(C(=O)O)cc2)cc1OC | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(CC(NC(=O)c1ccccc1)c1ccccc1)Nc1ccc(NC(=O)Nc2ccccc2)cc1 | C-C(-C)(-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 | 24 | HOUR | tert-Butyl-4-{[(1-(3,4-dimethoxyphenyl)-3-{[4-({[(2-methylphenyl)amino]carbonyl}amino) phenyl]amino}-3-oxopropyl)amino]carbonyl}benzoate (30 mg, 0.05 mmol) was dissolved in DCM (10 mL) and TFA (0.18 mL, 2.30 mmol) was added at 0° C. and the reaction mixture was stirred at r.t. for 24 h. The solvent was removed in vacuu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 24 | COc1ccc(C(CC(=O)Nc2ccc(NC(=O)Nc3ccccc3C)cc2)NC(=O)c2ccc(C(=O)OC(C)(C)C)cc2)cc1OC>C(Cl)Cl>COc1ccc(C(CC(=O)Nc2ccc(NC(=O)Nc3ccccc3C)cc2)NC(=O)c2ccc(C(=O)O)cc2)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d172a1b84e4647bc9c8687f1cd8f5dda | CC(C)(C)[Si](C)(C)Cl.COc1ccc2c(-c3ccc(OC)c(O)c3)coc2c1>>COc1ccc2c(-c3ccc(OC)c(O[Si](C)(C)C(C)(C)C)c3)coc2c1 | CC(C)(C)[Si](C)(C)Cl.OC=1C=C(C=CC1OC)C=1C2=C(OC1)C=C(C=C2)OC.CCN(CC)CC>>[Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1OC)C=1C2=C(OC1)C=C(C=C2)OC | Cl[Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([OH:15])[cH:23]3)[cH:24][o:25][c:26]2[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([O:15][Si:16]([CH3:17])([CH... | CC(C)(C)[Si](C)(C)Cl.COc1ccc2c(-c3ccc(OC)c(O)c3)coc2c1 | COc1ccc2c(-c3ccc(OC)c(O[Si](C)(C)C(C)(C)C)c3)coc2c1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccc(-c2coc3ccccc23)cc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 92.2 | [{"value": 92.0, "product": "[Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1OC)C=1C2=C(OC1)C=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "[Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1OC)C=1C2=C(OC1)C=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 14 (3.51 g, 12.9 mmol) in CH2Cl2 (30 mL), under nitrogen, was added Et3N (1.98 mL, 14.2 mmol) followed by DMAP (0.162 g, 14.2 mmol) and TBSCl (2.4 g, 14.2 mmol) at 0° C. The reaction mixture was stirred for 12 h allowing too reach room temperature. The reaction was quenched with water, the phases separ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1.c1ccc2occc2c1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 12 | CC(C)(C)[Si](C)(C)Cl.COc1ccc2c(-c3ccc(OC)c(O)c3)coc2c1>CN(C)C=1C=CN=CC1.C(Cl)Cl>COc1ccc2c(-c3ccc(OC)c(O[Si](C)(C)C(C)(C)C)c3)coc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c5bd52821714c9bb9e8153a9d33262f | COc1ccc(C=O)c(OC)c1OC>>COc1ccc(C=O)c(O)c1O | Cl.COC1=C(C=O)C=CC(=C1OC)OC.B(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>>OC1=C(C=O)C=CC(=C1O)OC | C[O:10][c:9]1[c:6]([CH:7]=[O:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]1[O:12]C>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([OH:10])[c:11]1[OH:12] | COc1ccc(C=O)c(OC)c1OC | COc1ccc(C=O)c(O)c1O | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[O;H0;D2;+0:7]-C):[c:8]>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2](-[OH;D1;+0:1]):[c:6](-[OH;D1;+0:7]):[c:8] | 73 | [{"value": 73.0, "product": "OC1=C(C=O)C=CC(=C1O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "OC1=C(C=O)C=CC(=C1O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A dry CH2Cl2 (200 mL) solution of 2,3,4-trimethoxybenzaldehyde (19.6 g, 100 mmol), under nitrogen, was stirred for 10 min and BCl3 (1.0M solution in CH2Cl2, 200 mL) was added. The reaction was stirred for 24 hours and a 10% sodium bicarbonate solution (40 g/360 mL) was added. The resulting solution was acidified with c... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 24 | COc1ccc(C=O)c(OC)c1OC>C(Cl)Cl>COc1ccc(C=O)c(O)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fcacfd8cbe564e93b9260f019b289944 | CC(C)Br.CCOC(C)=O.COc1ccc(C=O)c(O)c1O>>COc1ccc(C=O)c(OC(C)C)c1OC(C)C | OC1=C(C=O)C=CC(=C1O)OC.C(=O)([O-])[O-].[K+].[K+].O.CCOC(=O)C.BrC(C)C>>C(C)(C)OC1=C(C=O)C=CC(=C1OC(C)C)OC | Br[CH:16]([CH3:13])[CH3:17].O=[C:11](OC[CH3:18])[CH3:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([OH:10])[c:14]1[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([O:10][CH:11]([CH3:12])[CH3:13])[c:14]1[O:15][CH:16]([CH3:17])[CH3:18] | CC(C)Br.CCOC(C)=O.COc1ccc(C=O)c(O)c1O | COc1ccc(C=O)c(OC(C)C)c1OC(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 684858b2c020d9d6d36d1825ea5e12be6ae3975f64a028f56fa8e97d882f6a1c | 88ed51cd3eddf51d88767b8d4e94bf799aa7e96d44010d584a877b7adf2bfc8a | c1ccccc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[CH3;D1;+0:3].O=[C;H0;D3;+0:4](-[C;D1;H3:5])-O-C-[CH3;D1;+0:6].[O;D1;H0:7]=[C:8]-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[C;D1;H3:5]-[CH;D3;+0:4](-[CH3;D1;+0:3])-[O;H0;D2;+0:11]-[c:10](:[c:9]-[C:8]=[O;D1;H0:7]):[c:12](-[O;H0;D2;+0:13]-[CH;D3;+0:1](-[C;D1;H3:2])-[CH3;D1;... | 82 | [{"value": 82.0, "product": "C(C)(C)OC1=C(C=O)C=CC(=C1OC(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 21 (26.70 g, 158.7 mmol) in DMF (150 mL) under nitrogen, was added K2CO3 (65.84 g, 476.3 mmol) followed by 2-bromopropane (44.72 mL, 476.3 mmol) and heated to reflux (90° C.) for 12 hours. Water (200 mL) and EtOAc (200 mL) were added to the reaction mixture, the phases were separated, and the aqueous p... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HBr | CN(C)C=O | 90 | null | CC(C)Br.CCOC(C)=O.COc1ccc(C=O)c(O)c1O>CN(C)C=O>COc1ccc(C=O)c(OC(C)C)c1OC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-984178fe26d140788905778d11aa6935 | COc1ccc(C=O)c(OC(C)C)c1OC(C)C>>COc1ccc(C(C)O)c(OC(C)C)c1OC(C)C | C(C)(C)OC1=C(C=O)C=CC(=C1OC(C)C)OC.C[Li]>>C(C)(C)OC1=C(C=CC(=C1OC(C)C)OC)C(C)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:9])[c:10]([O:11][CH:12]([CH3:13])[CH3:14])[c:15]1[O:16][CH:17]([CH3:18])[CH3:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH3:8])[OH:9])[c:10]([O:11][CH:12]([CH3:13])[CH3:14])[c:15]1[O:16][CH:17]([CH3:18])[CH3:19] | COc1ccc(C=O)c(OC(C)C)c1OC(C)C | COc1ccc(C(C)O)c(OC(C)C)c1OC(C)C | null | null | C(C)OCC | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 84 | [{"value": 84.0, "product": "C(C)(C)OC1=C(C=CC(=C1OC(C)C)OC)C(C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 22 (23.10 g, 91.56 mmol) in dry ethyl ether (150 mL) was added dropwise methyllithium (98.10 mL, 1.4 M in EtO2, 1.37.3 mmol) at 0° C. under nitrogen. The reaction mixture was stirred for 2 h allowing too reach room temperature. The reaction was slowly quenched with water, the phases were separated, and... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccccc1 | Other | C(C)OCC | null | 2 | COc1ccc(C=O)c(OC(C)C)c1OC(C)C>C(C)OCC>COc1ccc(C(C)O)c(OC(C)C)c1OC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44b54a3e212a410d8860722b1d5535c3 | COc1cc(Br)cc(OC)c1OC>>[Li][c]1cc(OC)c(OC)c(OC)c1 | C(CCC)[Li].COC=1C=C(C=C(C1OC)OC)Br>>COC=1C=C(C=C(C1OC)OC)[Li] | Br[c:2]1[cH:3][c:4]([O:5][CH3:6])[c:7]([O:8][CH3:9])[c:10]([O:11][CH3:12])[cH:13]1>>[Li:1][c:2]1[cH:3][c:4]([O:5][CH3:6])[c:7]([O:8][CH3:9])[c:10]([O:11][CH3:12])[cH:13]1 | COc1cc(Br)cc(OC)c1OC | [Li][c]1cc(OC)c(OC)c(OC)c1 | null | null | CCOCC | Miscellaneous | Preparation of organolithium compounds | 09779d25a04d5c0f9dabfacc40aa046c53f91c14a1d59b1794183fd92ad3e2b7 | b74e09b9a6bbb0311fc1db764a25c5a719efefaac386e11fdf0023b3ff360a3e | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[Li;D1;H0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 1 | HOUR | To a stirred solution of n-butyllithium (3.7 mL, 1.6 M in hexane solution,6.0 mol) in dry ether (40 mL), a solution of 3,4,5-trimethoxyphenylbromide (0.74 g, 3.0 mol) in ether (20 mL) was added under dry nitrogen at −78° C. The solution was stirred for 1 h in order to form 3,4,5-trimethoxyphenyllithum (“TPL”). Substitu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aryl lithium | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CCOCC | null | 1 | COc1cc(Br)cc(OC)c1OC>CCOCC>[Li][c]1cc(OC)c(OC)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36a01d141f4a4baca50a7e0cdac2419d | ICCCCCI.O=C1Cc2ccccc2N1>>O=C1Nc2ccccc2C12CCCCC2 | ICCCCCI.N1C(CC2=CC=CC=C12)=O.C(CCC)[Li].[Cl-].[NH4+].CN(CCN(C)C)C>>N1C(C2(C3=CC=CC=C13)CCCCC2)=O | I[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]I.[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2 | ICCCCCI.O=C1Cc2ccccc2N1 | O=C1Nc2ccccc2C12CCCCC2 | null | null | CCOC(=O)C.O1CCCC1 | C-C Coupling | OtherReaction | 579f0f36d3c1f227acfe012179441842108aef707a45bbf7908129260433618c | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | O=C1Nc2ccccc2C12CCCCC2 | I-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-I.[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D4;+0:12]-12-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-2 | 69.6 | [{"value": 69.6, "product": "N1C(C2(C3=CC=CC=C13)CCCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.8, "product": "N1C(C2(C3=CC=CC=C13)CCCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of oxindole (25 g, 0.19 mol) in anhydrous tetrahydrofuran (800 cm3) was cooled to −20° C., then n-butyllithium (2.5M in hexanes, 152 cm3, 0.38 mol) was added slowly followed by N,N,N′,N′-tetramethylethylenediamine (51 cm3, 0.38 mol,). After 15 min. 1,5-diiodopentane (174 g, 0.54 mol) was added slowly and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | HI | CCOC(=O)C.O1CCCC1 | null | 0.25 | ICCCCCI.O=C1Cc2ccccc2N1>CCOC(=O)C.O1CCCC1>O=C1Nc2ccccc2C12CCCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19435386e3f9410d97590e76cde4c6c3 | BrBr.O=C1Nc2ccccc2C12CCCCC2>>O=C1Nc2ccc(Br)cc2C12CCCCC2 | N1C(C2(C3=CC=CC=C13)CCCCC2)=O.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3 | Br[Br:8].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:9][c:10]2[C:11]12[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[C:11]12[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2 | BrBr.O=C1Nc2ccccc2C12CCCCC2 | O=C1Nc2ccc(Br)cc2C12CCCCC2 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | b75a0cb1be6e87ac5ae2a0c4fc61b176231cdf76c6a5c5e00ef053906cd4efba | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Nc2ccccc2C12CCCCC2 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:3]:[c:2] | 67 | [{"value": 67.0, "product": "BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (17.6 g, 0.09 mol) in acetic acid (300 cm3) was added sodium acetate (8.0 g, 0.1 mol) and bromine (14.6 g, 0.091 mol) with stirring. After 30 min. at room temperature, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extra... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | HBr | C(C)(=O)O | null | 0.5 | BrBr.O=C1Nc2ccccc2C12CCCCC2>C(C)(=O)O>O=C1Nc2ccc(Br)cc2C12CCCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1716cb0b7ce4140b396a0bde09d0a6f | CN(C)C=O.Fc1cc(Br)cc(Br)c1>>O=Cc1cc(F)cc(Br)c1 | CN(C)C=O.BrC=1C=C(C=C(C1)Br)F.C(CCC)[Li]>>FC=1C=C(C=O)C=C(C1)Br | CN(C)[CH:2]=[O:1].Br[c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1 | CN(C)C=O.Fc1cc(Br)cc(Br)c1 | O=Cc1cc(F)cc(Br)c1 | null | null | C(C)OCC | C-C Coupling | Bouveault aldehyde synthesis | 4664d189e1ff40b394aee0a7d0943c7bfc06c1f81f238cff6865649dda594153 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-C)-[CH;D2;+0:6]=[O;D1;H0:7]>>[O;D1;H0:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 100 | [{"value": 100.0, "product": "FC=1C=C(C=O)C=C(C1)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3,5-dibromofluorobenzene in diethyl ether (100 cm3) at −78° C. was added n-butyl lithium (2.5 M, 8 cm3, 20 mmol) dropwise. After 30 min. the mixture was treated with DMF (20 cm3 diethyl ether (10 cm3 stirring was continued at −78° C. After 30 min. the mixture was quenched with dilute HCl aq., separated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)OCC | null | null | CN(C)C=O.Fc1cc(Br)cc(Br)c1>C(C)OCC>O=Cc1cc(F)cc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09c0fd12d8af423d9f04780d9705f1c8 | ON=Cc1cc(F)cc(Br)c1>>N#Cc1cc(F)cc(Br)c1 | FC=1C=C(C=NO)C=C(C1)Br>>FC=1C=C(C#N)C=C(C1)Br | O[N:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1 | ON=Cc1cc(F)cc(Br)c1 | N#Cc1cc(F)cc(Br)c1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(C)#N | Functional Group Interconversion | OtherReaction | 17f476cc256704e312f02cdb730538a4d2e78e129aaed9ef4aa555a9b052c890 | 9ad4e779dba60265752423413bc1b61ff9562539f91b24f3b3d9205e4bb46232 | c1ccccc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 89.3 | [{"value": 89.0, "product": "FC=1C=C(C#N)C=C(C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "FC=1C=C(C#N)C=C(C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | The above oxime (3.76 g, 17.24 mmol) and copper (II) acetate (370 mg) were dissolved in acetonitrile (100 cm3) under nitrogen and heated under reflux. After 5 h, the mixture was evaporated, the residue taken into EtOAc, washed with sulfuric acid (1N), water, brine, dried (MgSO4) and evaporated to give 3-fluoro-5-bromob... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Nitrile | null | null | c1ccccc1 | HO- | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)#N | null | 5 | ON=Cc1cc(F)cc(Br)c1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)#N>N#Cc1cc(F)cc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b8a828b260f43bca10e9f199504f305 | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCC2>>CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCC1)C(=O)N2 | BrC=1C=C2C3(C(NC2=CC1)=O)CCCC3.C(C)(C)(C)OC(=O)N1C(=CC=C1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>O=C1NC2=CC=C(C=C2C12CCCC2)C=2N(C=CC2)C(=O)OC(C)(C)C | OB(O)[c:12]1[n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:9][cH:10][cH:11]1.Br[c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[C:19]1([CH2:20][CH2:21][CH2:22][CH2:23]1)[C:24](=[O:25])[NH:26]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][cH:11][c:12]1-[c:13]1[cH:14][cH:15][c:16]2[c:17]([... | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCC2 | CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCC1)C(=O)N2 | 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.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | f4c0bb8a2ef20aeab29eef207992d304c861d6e70be458c5f816d6d34ebf1e84 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:15]-[C:14](-[C;D1;H3:16])(-[C;D1;H3:17])-[#8:13]-[C:11](=[O;D1;H0:12])-[#7;a:10]1:[c:9]:[c:8]:[c:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](... | 83.2 | [{"value": 83.0, "product": "O=C1NC2=CC=C(C=C2C12CCCC2)C=2N(C=CC2)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.2, "product": "O=C1NC2=CC=C(C=C2C12CCCC2)C=2N(C=CC2)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 5-(2′-Oxo-2′,3′-dihydrospiro[cyclopentane-1,3′-[3H]indol]-5′-yl-2-cyanopyrrole: A solution of 5′-bromospiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (2.0 g, 7.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (430 mg, 0.3 mmol) in ethylene glycol dimethyl ether (50 mL) was stirred under a flow of nitrogen for 15 min... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCC1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCC1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCC1 | 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.COCCOC | 80 | null | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCC2>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.COCCOC>CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCC1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89b28dbe8cec44cf9b69ba8d95d0eaad | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCCC2>>CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 | B(O)(O)C=1N(C=CC1)C(=O)OC(C)(C)C.C(=O)([O-])[O-].[K+].[K+].BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3>>O=C1NC2=CC=C(C=C2C12CCCCC2)C=2N(C=CC2)C(=O)OC(C)(C)C | OB(O)[c:12]1[n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:9][cH:10][cH:11]1.Br[c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[C:19]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[C:25](=[O:26])[NH:27]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][cH:11][c:12]1-[c:13]1[cH:14][cH:15][c:16]2... | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCCC2 | CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 | null | null | O | C-C Coupling | Suzuki coupling with boronic acids | 72cb0722e2dfbd8433f7f279041b17208e2a10c7d719ed09e6c4b6dd1c93185b | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:15]-[C:14](-[C;D1;H3:16])(-[C;D1;H3:17])-[#8:13]-[C:11](=[O;D1;H0:12])-[#7;a:10]1:[c:9]:[c:8]:[c:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](... | 77.3 | [{"value": 76.0, "product": "O=C1NC2=CC=C(C=C2C12CCCCC2)C=2N(C=CC2)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "O=C1NC2=CC=C(C=C2C12CCCCC2)C=2N(C=CC2)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 15 | MINUTE | To a solution of 5′-bromo-spiro[cyclohexane-1,3′-indolin]-2′-one (3.4 g, 12 mmol) in 1,2-DME (100 mL) under a nitrogen atmosphere was added tetrakis(triphenylphospine)palladium(0) (70 mg, 5 mol %). After 15 min, 2-borono-1H-pyrrole-1-carboxylic acid, 1-tert butyl ester (1.3 eq, 3.31 g, 15.6 mmol) and a solution of K2CO... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | O | 80 | 0.25 | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCCC2>O>CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70f66bc6736f4a80ac413ff2db27ac21 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cn1c(C#N)ccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2>>Cn1c(C#N)ccc1-c1ccc2c(c1)C1(CCCCC1)C(=S)N2 | O.O=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC=C(N2C)C#N.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>S=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC=C(N2C)C#N | COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:22])S2)cc1.O=[C:21]1[C:15]2([c:13]3[c:12]([cH:11][cH:10][c:9](-[c:8]4[n:2]([CH3:1])[c:3]([C:4]#[N:5])[cH:6][cH:7]4)[cH:14]3)[NH:23]1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2>>[CH3:1][n:2]1[c:3]([C:4]#[N:5])[cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]1([CH2:16]... | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cn1c(C#N)ccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 | Cn1c(C#N)ccc1-c1ccc2c(c1)C1(CCCCC1)C(=S)N2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | ca3e51120f3a4b20097412f955afcc8b20206caa645bcb7aa2c74ea9fa008f79 | 558580c5823c2cfab2cae548a45ef991ba9b53d2e5812b481e23ff3540a5940e | S=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCCC2 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2]1-[#7:3]-[c:4]:[c:5]-[C:6]-1(-[C:7])-[C:8]>>[C:7]-[C:6]1(-[C:8])-[c:5]:[c:4]-[#7:3]-[C;H0;D3;+0:2]-1=[S;H0;D1;+0:1] | 90.5 | [{"value": 55.0, "product": "S=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC=C(N2C)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "S=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC=C(N2C)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 5-(2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-pyrrole-2-carbonitrile (0.55 g, 1.8 mmol, 1 eq) in toluene (50 mL) was added Lawesson's reagent (0.47 g, 1.1 mmol, 0.65 eq) and the reaction was heated to 80° C. for 1 hour. The reaction was cooled to room temperature, poured into water (100 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amide.Monosulfide.Monosulfide | Thioamide | c1ccccc1.P1SPS1.c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | Other | C1(=CC=CC=C1)C | 80 | null | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cn1c(C#N)ccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2>C1(=CC=CC=C1)C>Cn1c(C#N)ccc1-c1ccc2c(c1)C1(CCCCC1)C(=S)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70fbe5d426504ba9b0472297ac3af260 | ICCCCI.O=C1Cc2ccccc2N1>>O=C1Nc2ccccc2C12CCCC2 | N1C(CC2=CC=CC=C12)=O.C(CCC)[Li].ICCCCI.CN(CCN(C)C)C>>N1C(C2(C3=CC=CC=C13)CCCC2)=O | I[CH2:11][CH2:12][CH2:13][CH2:14]I.[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH2:14]2 | ICCCCI.O=C1Cc2ccccc2N1 | O=C1Nc2ccccc2C12CCCC2 | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | da305b19e438cec6dd9ecd353ca3cd934886dd4c5b3846022dac2a623fceb79e | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | O=C1Nc2ccccc2C12CCCC2 | I-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-I.[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D4;+0:11]-12-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-2 | 50 | [{"value": 50.0, "product": "N1C(C2(C3=CC=CC=C13)CCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "N1C(C2(C3=CC=CC=C13)CCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a −25° C. solution of oxindole (2.0 g, 15.0 mmol) in 40 (cm3) of anhydrous THF under N2 was added n-butyllithium (1.6 M in hexanes, 19.7 cm3, 31.5 mmol) drop-wise. To the resulting milky solution was added N,N,N′,N′-tetramethylethylenediamine (4.75 cm3, 31.5 mmol). After 30 min. a solution of 1,4-diiodobutane (21.9 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | HI | C1CCOC1.O | null | 14 | ICCCCI.O=C1Cc2ccccc2N1>C1CCOC1.O>O=C1Nc2ccccc2C12CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f40b35095113458e955889004f700469 | BrBr.O=C1Nc2ccccc2C12CCCC2>>O=C1Nc2ccccc2C12CCCC2Br | C(O)([O-])=O.[Na+].N1C(C2(C3=CC=CC=C13)CCCC2)=O.C(C)(=O)[O-].[Na+].BrBr>>BrC1CCCC12C(NC1=CC=CC=C21)=O | Br[Br:15].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH2:14]2>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH:14]2[Br:15] | BrBr.O=C1Nc2ccccc2C12CCCC2 | O=C1Nc2ccccc2C12CCCC2Br | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 5d1ae453742bff017caef24079c4e11e210e4fe7fcd315c0a1d757dce473ae36 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=C1Nc2ccccc2C12CCCC2 | Br-[Br;H0;D1;+0:1].[O;D1;H0:2]=[C:3]1-[#7:4]-[c:5]:[c:6]-[C:7]-12-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-2>>[Br;H0;D1;+0:1]-[CH;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:7]-12-[c:6]:[c:5]-[#7:4]-[C:3]-2=[O;D1;H0:2] | 105 | [{"value": 96.0, "product": "BrC1CCCC12C(NC1=CC=CC=C21)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 105.0, "product": "BrC1CCCC12C(NC1=CC=CC=C21)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (0.27 g, 1.4 mmol) and sodium acetate (0.12 g, 1.46 mmol) in acetic acid (10 cm3) was treated with bromine (0.24 g, 1.51 mmol) in acetic acid (2 cm3). After 30 min. the mixture was poured into sat. sodium hydrogen carbonate solution and extracted with EtOAc (... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | HBr | C(C)(=O)O | null | null | BrBr.O=C1Nc2ccccc2C12CCCC2>C(C)(=O)O>O=C1Nc2ccccc2C12CCCC2Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00d03b2c1c3b4c2a908a9d526535d5cd | N#Cc1cc(F)cc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O>>N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 | C([O-])([O-])=O.[Na+].[Na+].C(#N)C=1C=C(C=C(C1)F)Br.[OH-].[Na+].N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O>>C(#N)C=1C=C(C=C(C1)F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3 | Br[c:8]1[cH:7][c:5]([F:6])[cH:4][c:3]([C:2]#[N:1])[cH:23]1.OB(O)[CH:19]1[C:15]2([c:13]3[c:12]([cH:11][cH:10][cH:9][cH:14]3)[NH:22][C:20]2=[O:21])[CH2:16][CH2:17][CH2:18]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[C:15]2([CH2:16][CH2:17][CH2:18][CH2:19]2)[C:20](=[O:21])... | N#Cc1cc(F)cc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O | N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 | null | null | O.COCCOC | C-C Coupling | OtherReaction | 730dcdc10a1abdabad91331a2b6e5cbbf0777aa3d68588c0d603eed6404753ea | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-12-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[c:18]:[c:19]:1-2>>[O;D1;H0:12]=[C:11]1-[#7:13]-[c:14]2:[c:15]:[c:16]:[c;H0;D3;+0:17](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:18]:[c:19]:2-[C:10]-12-[C:9]... | 44 | [{"value": 44.0, "product": "C(#N)C=1C=C(C=C(C1)F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "C(#N)C=1C=C(C=C(C1)F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-cyano-5-fluoro-bromobenzene (0.5 g, 2.6 mmol), and tetrakis (triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl)boronic acid (0.9 g, 3.9 mmol) and sodi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | HBr.B | O.COCCOC | null | null | N#Cc1cc(F)cc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O>O.COCCOC>N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9142de5693444da9440ade37d4c5c15 | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>>CC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | BrC=1C=C2C(C(NC2=CC1)=O)(C)C.ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C | Br[c:10]1[cH:9][cH:8][c:7]2[c:19]([cH:18]1)[C:2]([CH3:1])([CH3:3])[C:4](=[O:5])[NH:6]2.OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]3)[cH:18][c:19]21 | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1 | CC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | 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(OC)COC.[Cl-].[NH4+] | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 25 | [{"value": 25.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (0.98 g, 4.07 mol) and tetrakis(triphenylphosphine)palladium(0) (0.239 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (35 cm3). After 15 min., 3-chlorophenylboronic acid (1.27 g, 8.13 mol) was added, followed by potassium carbonate (3.40 g, 45 mmol) in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC.[Cl-].[NH4+] | null | 0.25 | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC.[Cl-].[NH4+]>CC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c1602386b2f47d482b05454e4845707 | CC1(Cc2ccccc2)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(Cc2ccccc2)C(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 | C(C1=CC=CC=C1)C1(C(NC2=CC=C(C=C12)C1=CC(=CC=C1)Cl)=O)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>C(C1=CC=CC=C1)C1(C(NC2=CC=C(C=C12)C1=CC(=CC=C1)Cl)=S)C | O=[C:10]1[C:2]([CH3:1])([CH2:3][c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:25]2[c:13]([cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[cH:24]2)[NH:12]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:11])S2)cc1>>[CH3:1][C:2]1([CH2:3][c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[C:10](=[S:11])[NH:12][c:13]2[cH:14][cH... | CC1(Cc2ccccc2)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(Cc2ccccc2)C(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 5ed7a1677d229b16df832cbfd7a180a5851f4818c8175b9dd146291c84305872 | 558580c5823c2cfab2cae548a45ef991ba9b53d2e5812b481e23ff3540a5940e | S=C1Nc2ccc(-c3ccccc3)cc2C1Cc1ccccc1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2]1-[#7:3]-[c:4]:[c:5]-[C:6]-1(-[C:7])-[C;D1;H3:8]>>[C:7]-[C:6]1(-[C;D1;H3:8])-[c:5]:[c:4]-[#7:3]-[C;H0;D3;+0:2]-1=[S;H0;D1;+0:1] | 21 | [{"value": 21.0, "product": "C(C1=CC=CC=C1)C1(C(NC2=CC=C(C=C12)C1=CC(=CC=C1)Cl)=S)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 3-benzyl-5-(3-chloro-phenyl)-3-methyl-1,3-dihydro-indol-2-one (100 mg) and Lawesson's reagent (120 mg) in toluene (10 ml) at reflux, according to General Procedure A, to afford the title compound (0.022 g) as an off white solid: mp. 168–170° C.; 1H NMR (CDCl3) δ 9.23 (br s, 1H), 7.4... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)CCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | CC1(Cc2ccccc2)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CC1(Cc2ccccc2)C(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1410de5373474c20b5b594a894ba44f8 | BrBr.CC1(C)C(=O)Nc2ccccc21>>CC1(C)C(=O)Nc2ccc(Br)cc21 | C([O-])([O-])=O.[Na+].[Na+].CC1(C(NC2=CC=CC=C12)=O)C.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2C(C(NC2=CC1)=O)(C)C | Br[Br:11].[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][cH:10][cH:12][c:13]21>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]21 | BrBr.CC1(C)C(=O)Nc2ccccc21 | CC1(C)C(=O)Nc2ccc(Br)cc21 | null | null | O.C(C)(=O)O | Functional Group Interconversion | Bromination | e5aad40fc3ec640bed45a7119ff569558b20c39979304f365dafdbc5ae4e4cd4 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Cc2ccccc2N1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 92 | [{"value": 92.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 50 | MINUTE | 3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mixture. The reaction was stirred for 50 min., then poured into water. The mixture was basified with sodium ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HBr | O.C(C)(=O)O | null | 0.833333 | BrBr.CC1(C)C(=O)Nc2ccccc21>O.C(C)(=O)O>CC1(C)C(=O)Nc2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50462c2ef19b45b9985f6de89953a1bc | CC1(C)C(=O)Nc2ccc(Br)cc21.COc1cccc(B(O)O)c1>>COc1cccc(-c2ccc3c(c2)C(C)(C)C(=O)N3)c1 | [Cl-].[NH4+].BrC=1C=C2C(C(NC2=CC1)=O)(C)C.COC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])([CH3:16])[C:17](=[O:18])[NH:19]2.OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20]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]3[c:12]([cH:13]2)[C:14]([CH3:15])([CH3:16])[C:17](=[O:18])[NH:19]3)[cH:20]1 | CC1(C)C(=O)Nc2ccc(Br)cc21.COc1cccc(B(O)O)c1 | COc1cccc(-c2ccc3c(c2)C(C)(C)C(=O)N3)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 | CCOC(=O)C.O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 31 | [{"value": 31.0, "product": "COC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.8, "product": "COC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (0.33 g, 1.38 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.094 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (12 cm3). After 15 minutes, 3-methoxyphenylboronic acid (0.42 g, 2.76 mmol) was added, followed by potassium carbonate (1.15 g, 8.34 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2 | 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.CCOC(=O)C.O.C(OC)COC | null | 0.25 | CC1(C)C(=O)Nc2ccc(Br)cc21.COc1cccc(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C.O.C(OC)COC>COc1cccc(-c2ccc3c(c2)C(C)(C)C(=O)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89c517760b0f47fbbd4ca1ae0d7c1d26 | CN(C)C=O.Cc1ccsc1Br>>Cc1cc(C=O)sc1Br | BrC=1SC=CC1C.C(C)NCC.[Li]CCCC.CN(C)C=O>>BrC1=C(C=C(S1)C=O)C | CN(C)[CH:5]=[O:6].[CH3:1][c:2]1[cH:3][cH:4][s:7][c:8]1[Br:9]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]=[O:6])[s:7][c:8]1[Br:9] | CN(C)C=O.Cc1ccsc1Br | Cc1cc(C=O)sc1Br | null | null | C1CCOC1.CCCCCC | C-C Coupling | OtherReaction | 77a8917ac8ed8f2ad464b767187c983c24a719c711c4936bfe09b270792882f5 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccsc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#16;a:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:7]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1 | 88.3 | [{"value": 88.3, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 30 | MINUTE | To a solution of diethylamine (28 g, 0.383 mol) in anhydrous THF (400 mL) was added at −40° C. under nitrogen a solution of n-BuLi (2.5 M, 153 mL, 0.383 mol) in hexane. After addition, the solution was stirred at −40° C. under nitrogen for 30 minutes, cooled to −78° C. and treated dropwise with a solution of 2-bromo-3-... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccsc1 | c1ccsc1 | c1ccsc1 | Other | C1CCOC1.CCCCCC | -40 | 0.5 | CN(C)C=O.Cc1ccsc1Br>C1CCOC1.CCCCCC>Cc1cc(C=O)sc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-919f5637e2fc42948973a9ffeda0599d | CCI.O=C1Cc2ccccc2N1>>CCC1=c2ccccc2=NC1=O | ICC.N1C(CC2=CC=CC=C12)=O.C(CCC)[Li].[NH4+].[Cl-].CN(CCN(C)C)C>>C(C)C=1C(N=C2C=CC=CC12)=O | I[CH2:2][CH3:1].[CH2:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11]1=[O:12]>>[CH3:1][CH2:2][C:3]1=[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2=[N:10][C:11]1=[O:12] | CCI.O=C1Cc2ccccc2N1 | CCC1=c2ccccc2=NC1=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 7f8efd166912a03506850ad77dd8b310e9bbf110f40dc0aa3466aad53303d70b | 9795126e672adf3dfeb9ebcd165d02e10eb1b4ac31d83997fdca7c7a739d39dc | O=C1C=c2ccccc2=N1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[C:4]1-[CH2;D2;+0:5]-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2-[NH;D2;+0:12]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:5]1=[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2=[N;H0;D2;+0:12]-[C:4]-1=[O;D1;H0:3] | 2.9 | [{"value": 2.9, "product": "C(C)C=1C(N=C2C=CC=CC12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of oxindole (40 g, 0.3 mol) in dry THF (400 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyl lithium (2.5M in hexanes, 240 ml, 0.6 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (90.4 ml, 0.6 mol). After 30 min. iodoethane (48 ml, 0.6 mol) was added and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | null | c1ccc2c(c1)CCN2 | C1=c2ccccc2=NC1 | C1=c2ccccc2=NC1 | HI | C1CCOC1 | null | null | CCI.O=C1Cc2ccccc2N1>C1CCOC1>CCC1=c2ccccc2=NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b44cd7d278c4cc8bad2b58a6a049672 | CCC1=c2ccccc2=NC1=O.CCI>>CCC1(CC)C(=O)Nc2ccccc21 | ICC.C(C)C=1C(N=C2C=CC=CC12)=O.C(CCC)[Li].[NH4+].[Cl-].CN(CCN(C)C)C>>C(C)C1(C(NC2=CC=CC=C12)=O)CC | [C:3]1([CH2:4][CH3:5])=[c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)=[N:8][C:6]1=[O:7].I[CH2:2][CH3:1]>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21 | CCC1=c2ccccc2=NC1=O.CCI | CCC1(CC)C(=O)Nc2ccccc21 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | f15f58906703f12b51d1da977226590dc73f51d4fa9868a7b3d7ebfdcc2201e7 | 53812deded8d8876ba2f198bf967d0e3a8cebb6ae8cbe5dd02b6ae90ad0b6669 | O=C1Cc2ccccc2N1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[C:4]-[C;H0;D3;+0:5]1=[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2=[N;H0;D2;+0:12]-[C:13]-1=[O;D1;H0:14]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:5]1(-[C:4]-[C;D1;H3:3])-[C:13](=[O;D1;H0:14])-[NH;D2;+0:12]-[c;H0;D3;+0:11]2:[c:10]:[c:9]:[c:8]:[c:7]:[c;H0;D3;+0:6]:2-1 | 47.6 | [{"value": 45.0, "product": "C(C)C1(C(NC2=CC=CC=C12)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.6, "product": "C(C)C1(C(NC2=CC=CC=C12)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-ethyl-indol-2-one (16 g, 0.1 mol) in dry THF (200 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyllithium (2.5M in hexanes, 80 ml, 0.2 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (30 ml, 0.2 mol). After 30 min. iodoethane (8 ml, 0.1 mol) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Secondary amide | C1=c2ccccc2=NC1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | I- | C1CCOC1 | null | null | CCC1=c2ccccc2=NC1=O.CCI>C1CCOC1>CCC1(CC)C(=O)Nc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-556c1aea34984edebf71a28e879e10a3 | BrBr.CCC1(CC)C(=O)Nc2ccccc21>>CCC1(CC)C(=O)Nc2ccc(Br)cc21 | C(C)C1(C(NC2=CC=CC=C12)=O)CC.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2C(C(NC2=CC1)=O)(CC)CC | Br[Br:13].[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:14][c:15]21>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]21 | BrBr.CCC1(CC)C(=O)Nc2ccccc21 | CCC1(CC)C(=O)Nc2ccc(Br)cc21 | null | null | O.C(C)(=O)O | Functional Group Interconversion | Bromination | e5aad40fc3ec640bed45a7119ff569558b20c39979304f365dafdbc5ae4e4cd4 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Cc2ccccc2N1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | null | [] | null | null | null | null | A solution of 3,3-diethylindol-2-one (8 g, 40 mmol) and sodium acetate (4 g, 48 mmol) in acetic acid (100 ml) was treated with bromine (6.4 g, 40 mmol). After 30 min. the mixture was diluted with water and extracted with EtOAc (2×); the combined organic layers were washed with water, sat. sodium hydrogen carbonate solu... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HBr | O.C(C)(=O)O | null | null | BrBr.CCC1(CC)C(=O)Nc2ccccc21>O.C(C)(=O)O>CCC1(CC)C(=O)Nc2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ee58afad1c54d4ca431da562fb42f20 | CCC1(CC)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>>CCC1(CC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | BrC=1C=C2C(C(NC2=CC1)=O)(CC)CC.ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(CC)CC | Br[c:12]1[cH:11][cH:10][c:9]2[c:21]([cH:20]1)[C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[C:6](=[O:7])[NH:8]2.OB(O)[c:13]1[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]3)[cH:20][c:21]21 | CCC1(CC)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1 | CCC1(CC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | 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(OC)COC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 27 | [{"value": 27.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.7, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-bromo-1,3-dihydro-3,3-diethyl-[2H]-indol-2-one (2.7 g, 10 mmol), 3-chlorophenylboronic acid (1.6 g, 10 mmol), potassium carbonate (4 g, 30 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) in dimethoxyethane (100 ml), ethanol (25 ml), and water (25 ml) was heated to reflux for 6 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC.C(C)O | null | null | CCC1(CC)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC.C(C)O>CCC1(CC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2ba3a136dae496caa6ed5d95948979f | CCC1(CC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CCC1(CC)C(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 | ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(CC)CC.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=S)(CC)CC | O=[C:6]1[C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[c:21]2[c:9]([cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]3)[cH:20]2)[NH:8]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:7])S2)cc1>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[C:6](=[S:7])[NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([Cl:18]... | CCC1(CC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CCC1(CC)C(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 5ed7a1677d229b16df832cbfd7a180a5851f4818c8175b9dd146291c84305872 | 558580c5823c2cfab2cae548a45ef991ba9b53d2e5812b481e23ff3540a5940e | S=C1Cc2cc(-c3ccccc3)ccc2N1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2]1-[#7:3]-[c:4]:[c:5]-[C:6]-1(-[C:7])-[C:8]>>[C:7]-[C:6]1(-[C:8])-[c:5]:[c:4]-[#7:3]-[C;H0;D3;+0:2]-1=[S;H0;D1;+0:1] | null | [] | null | null | null | null | The title compound was prepared from 5-(3-chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one compound (100 mg) and Lawesson's reagent (100 mg) in toluene (10 ml) at reflux, according to General Procedure A, to afford the product (0.023 g) as a yellow solid: 1H NMR (DMSO-d6) δ 12.73 (br s, 1H), 7.77 (t, 1H, J=1.8 Hz), 7... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)CCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | CCC1(CC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CCC1(CC)C(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a5db7c4f64e47bcb8b812a4d9f7db0b | CSC1=Nc2ccc(Br)cc2C12CCCCC2.NOCc1ccccc1>>Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2 | BrC=1C=C2C3(C(=NC2=CC1)SC)CCCCC3.Cl.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)Br | CS[C:14]1=[N:24][c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:7][c:6]2[C:8]12[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2.[NH2:15][O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[C:14](=[N:15][O:16][CH2:17][c:18]1[cH:19][cH:20][cH:2... | CSC1=Nc2ccc(Br)cc2C12CCCCC2.NOCc1ccccc1 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | b7e408d847daf7a54697e7f466696f5de562d32f1fb12304c1fd1aaf97ca6430 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc(CON=C2Nc3ccccc3C23CCCCC3)cc1 | C-S-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[C:6]-1(-[C:7])-[C:8].[C:9]-[#8:10]-[NH2;D1;+0:11]>>[C:7]-[C:6]1(-[C:8])-[c:5]:[c:3](:[c:4])-[NH;D2;+0:2]-[C;H0;D3;+0:1]-1=[N;H0;D2;+0:11]-[#8:10]-[C:9] | null | [] | 45 | CELSIUS | null | null | 5′-Bromo-2′-(methylthio)spiro[cyclohexane-1,3′-[3H]indole] (9.0 g, 28.98 mmol) and O-benzylhydroxylamine hydrochloride (13.8 g, 86.9 mmol) were combined in methanol (150 mL) and heated to 45° C. for 6 hours. Methanol was evaporated in vacuo. Ethyl acetate was added to the residue and this mixture was washed with ammoni... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | C1=Nc2ccccc2C12CCCCC2 | c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | Other | CO | 45 | null | CSC1=Nc2ccc(Br)cc2C12CCCCC2.NOCc1ccccc1>CO>Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a3ce03affcd467280633224e16787b9 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.OB(O)c1ccc(F)cc1>>Fc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)cc1 | CCCCCC.C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)Br.FC1=CC=C(C=C1)B(O)O>>C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC=C(C=C2)F | Br[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[C:18](=[N:19][O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[NH:28]2.OB(O)[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:30][cH:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[C:12]2([CH2:13][CH2:14][... | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.OB(O)c1ccc(F)cc1 | Fc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)cc1 | null | null | C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 8734c5dd9f1a6e6409bcbbc53c99a0241dd1b8ab9806eccd050fa6b5202b7ad6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(CON=C2Nc3ccc(-c4ccccc4)cc3C23CCCCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 67 | [{"value": 67.0, "product": "C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol), and 4-fluorophenyl boronic acid (0.72 g, 5.2 mmol) according to Example 45 procedure A. The product was purified by flash silica gel chromatography; (eluant: 10:0.5 hexane:ethyl acetate) to give the desired product ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)NCC21CCCCC1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | C(C)(=O)OCC | null | null | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.OB(O)c1ccc(F)cc1>C(C)(=O)OCC>Fc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7b50e2533454ec0abc01181cf564b57 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.OB(O)c1ccc(F)c(F)c1>>Fc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)cc1F | C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)Br.FC=1C=C(C=CC1F)B(O)O>>C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=C(C=C2)F)F | Br[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[C:18](=[N:19][O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[NH:28]2.OB(O)[c:5]1[cH:4][cH:3][c:2]([F:1])[c:30]([F:31])[cH:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[C:12]2([CH2:13][C... | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.OB(O)c1ccc(F)c(F)c1 | Fc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)cc1F | null | null | C1CCOC1.O | C-C Coupling | Suzuki coupling with boronic acids | 8734c5dd9f1a6e6409bcbbc53c99a0241dd1b8ab9806eccd050fa6b5202b7ad6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(CON=C2Nc3ccc(-c4ccccc4)cc3C23CCCCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 69 | [{"value": 69.0, "product": "C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=C(C=C2)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3,4-diflurophenyl boronic acid (1.6 g, 5.2 mmol of a 50% solution of acid in THF/water) according to Example 45 procedure A. The product was purified by flash silica gel chromatography (eluant: 10:0.5 hexane:ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)NCC21CCCCC1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | C1CCOC1.O | null | null | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.OB(O)c1ccc(F)c(F)c1>C1CCOC1.O>Fc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-505d378986564b289b6586ca9291e8b6 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.COc1cccc(B(O)O)c1>>COc1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)c1 | CCCCCC.C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)Br.COC=1C=C(C=CC1)B(O)O>>C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=CC=C2)OC | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[C:20](=[N:21][O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[NH:30]2.OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31]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]3[c:12]([cH:13]2)[C... | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.COc1cccc(B(O)O)c1 | COc1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)c1 | null | null | C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 8734c5dd9f1a6e6409bcbbc53c99a0241dd1b8ab9806eccd050fa6b5202b7ad6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(CON=C2Nc3ccc(-c4ccccc4)cc3C23CCCCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 75 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3-methoxyphenyl boronic acid (0.79 g, 5.2 mmol) according to Example 45 procedure A. The product was purified by flash silica gel chromatography; (eluant: 10:0.5 hexane:ethyl acetate) to give the desired product ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)NCC21CCCCC1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | C(C)(=O)OCC | null | null | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.COc1cccc(B(O)O)c1>C(C)(=O)OCC>COc1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0339de4b5b6c487c862e7caab6206f02 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.O=[N+]([O-])c1cccc(B(O)O)c1>>O=[N+]([O-])c1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)c1 | C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)Br.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O>>C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=CC=C2)[N+](=O)[O-] | Br[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:21](=[N:22][O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[NH:31]2.OB(O)[c:8]1[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:32]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3... | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.O=[N+]([O-])c1cccc(B(O)O)c1 | O=[N+]([O-])c1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 8734c5dd9f1a6e6409bcbbc53c99a0241dd1b8ab9806eccd050fa6b5202b7ad6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(CON=C2Nc3ccc(-c4ccccc4)cc3C23CCCCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 55 | [{"value": 55.0, "product": "C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=CC=C2)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.8, "product": "C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)C2=CC(=CC=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3-Nitrophenyl boronic acid (0.86 g, 5.2 mmol) according to Example 45 procedure A. Purification by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate) afforded the desired compound (0.60 g, 1.4 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)NCC21CCCCC1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | null | null | null | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.O=[N+]([O-])c1cccc(B(O)O)c1>>O=[N+]([O-])c1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NOCc2ccccc2)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c8aec81ccc749b5850d7d06995e26e2 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.N#Cc1cccc(B(O)O)c1>>N#Cc1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NO)N3)c1 | C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)Br.C(#N)C=1C=C(C=CC1)B(O)O>>C(#N)C=1C=C(C=CC1)C=1C=C2C3(C(NC2=CC1)=NO)CCCCC3 | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[C:20](=[N:21][O:22]Cc1ccccc1)[NH:23]2.OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[C:14]2([CH2:15][CH2:16][CH2:17][CH2:18][CH2:1... | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.N#Cc1cccc(B(O)O)c1 | N#Cc1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NO)N3)c1 | null | null | C(C1=CC=CC=C1)#N | C-C Coupling | OtherReaction | 07b6e6d68ffe0d8fe0c6094199408af1101acbbbfc3a96507d90206e95662212 | e4b7a679ed09f6e9e384aa87a819f1defd661035a1c737866741e2bca62ab2cd | N=C1Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]-[C:5](=[#7:6]-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1)-[#7:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#7:8]-[C:5](=[#7:6]-[OH;D1;+0:7])-[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:9]:[c:10] | 71 | [{"value": 71.0, "product": "C(#N)C=1C=C(C=CC1)C=1C=C2C3(C(NC2=CC1)=NO)CCCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "C(#N)C=1C=C(C=CC1)C=1C=C2C3(C(NC2=CC1)=NO)CCCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[Spiro[cyclohexane-1,3′-[3H]indol]-(1′H)-one-2′-(O-benzyloxime)]benzonitrile[3H]indol]-5-yl]benzonitrile. Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3-cyanophenyl boronic acid (0.76 g, 5.2 mmol) according to Example 45 procedure A. The product was purif... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | Oxime | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | C(C1=CC=CC=C1)#N | null | null | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.N#Cc1cccc(B(O)O)c1>C(C1=CC=CC=C1)#N>N#Cc1cccc(-c2ccc3c(c2)C2(CCCCC2)C(=NO)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-542e11faf0c04255953d092e54cc0035 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.N#Cc1cc(F)cc(Br)c1>>N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=NO)N3)c1 | C(C1=CC=CC=C1)ON=C1NC2=CC=C(C=C2C12CCCCC2)Br.C([O-])([O-])=O.[Na+].[Na+].FC=1C=C(C=C(C1)C#N)Br.C(C)(=O)[O-].[K+]>>ON=C1NC2=CC=C(C=C2C12CCCCC2)C=2C=C(C#N)C=C(C2)F | Br[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:21](=[N:22][O:23]Cc1ccccc1)[NH:24]2.Br[c:8]1[cH:7][c:5]([F:6])[cH:4][c:3]([C:2]#[N:1])[cH:25]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[C:15]2([CH2:16][CH2:17][CH2:18][CH... | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.N#Cc1cc(F)cc(Br)c1 | N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=NO)N3)c1 | null | Cl[Pd]Cl.Cl[Pd]Cl | CN(C)C=O | C-C Coupling | OtherReaction | ef2298fe43b7ac763c63c8842faa33441ac9511774f9ae9610bb64b322049b00 | c817a1ff3d935ee2a58f4808dfe267bc36b8ffa48b144e313e0aa8a164a83fc5 | N=C1Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]-[C:11]-[C:12](=[#7:13]-[O;H0;D2;+0:14]-C-c1:c:c:c:c:c:1)-[#7:15]>>[#7:15]-[C:12](=[#7:13]-[OH;D1;+0:14])-[C:11]-[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 66 | [{"value": 66.0, "product": "ON=C1NC2=CC=C(C=C2C12CCCCC2)C=2C=C(C#N)C=C(C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "ON=C1NC2=CC=C(C=C2C12CCCCC2)C=2C=C(C#N)C=C(C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | To a solution of 3-fluoro-5-cyano-bromobenzene (0.4 g, 2.0 mmol) in dry DMF (10 ml) was added diboron pinacolate ester (0.63 g, 2.5 mmol), potassium acetate (0.65 g, 6.7 mmol) and PdCl2 (dppf) (0.2 g) and the reaction was heated to 80° C. under a nitrogen atmosphere. After 8 h. from 5′-bromospiro{cyclohexane-1,3′-[3H]i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | Oxime | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr | Cl[Pd]Cl.Cl[Pd]Cl.CN(C)C=O | 80 | 8 | Brc1ccc2c(c1)C1(CCCCC1)C(=NOCc1ccccc1)N2.N#Cc1cc(F)cc(Br)c1>Cl[Pd]Cl.Cl[Pd]Cl.CN(C)C=O>N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=NO)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9e750599b754d7482e18a1d5914ad02 | NN.O.ONC1CCCCC12C=Nc1ccc(-c3cccc(Cl)c3)cc12>>NC1=Nc2ccc(-c3cccc(Cl)c3)cc2C12CCCCC2.[NH4+].[OH-] | ClC=1C=C(C=CC1)C=1C=C2C3(C=NC2=CC1)C(CCCC3)NO.O.NN>>[OH-].[NH4+].ClC=1C=C(C=CC1)C=1C=C2C3(C(=NC2=CC1)N)CCCCC3 | [NH2:1][NH2:23].[OH2:24].ON[CH:22]1[C:17]2([CH:2]=[N:3][c:4]3[cH:5][cH:6][c:7](-[c:8]4[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]4)[cH:15][c:16]32)[CH2:18][CH2:19][CH2:20][CH2:21]1>>[NH2:1][C:2]1=[N:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[cH:15][c:16]2[C:17]12[CH2:18][CH2:19][CH2:20... | NN.O.ONC1CCCCC12C=Nc1ccc(-c3cccc(Cl)c3)cc12 | NC1=Nc2ccc(-c3cccc(Cl)c3)cc2C12CCCCC2.[NH4+].[OH-] | null | [Ni] | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 4b8d9cea12497294d88671b36f0603d21a5cc32675f08f66455fb407789c7e10 | 247f27afc29ce267bfe640918462fc5d7b8113f354fd4db111896ba3ae4e0a45 | C1=Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | O-N-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4]1(-[C:5])-[CH;D2;+0:6]=[#7:7]-[c:8]:[c:9]-1.[NH2;D1;+0:10]-[NH2;D1;+0:11].[OH2;D0;+0:12]>>[C:5]-[C:4]1(-[CH2;D2;+0:1]-[C:2]-[C:3])-[c:9]:[c:8]-[#7:7]=[C;H0;D3;+0:6]-1-[NH2;D1;+0:10].[NH4+;D0:11].[OH-;D0:12] | 130.4 | [{"value": 0.1, "product": "[OH-].[NH4+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C3(C(=NC2=CC1)N)CCCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 130.4, "product": "ClC=1C=C(C=CC1)C=1C=C2C3(C(=NC2=CC1)N)CCCCC3", "details": "CALCULATEDPERCEN... | 55 | CELSIUS | 45 | MINUTE | To a turbid solution of 5′-(3-Chlorophenyl)-N-hydroxyspiro[cyclohexane-1,3-[3H]indol]-2-amine (0.500 g; 1.53 mmol) in 25 mL of ethanol was added hydrazine hydrate (0.600 mL; 12.24 mmol). The solution was warmed to 55° C., where Raney-nickel (50% in water) was added to the reaction to keep a constant evolution of gas. A... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Substituted imine.Secondary amine | Primary amine | C1=Nc2ccccc2C12CCCCC2 | C1=Nc2ccccc2C12CCCCC2 | c1ccccc1.C1=Nc2ccccc2C12CCCCC2 | HO- | [Ni].C(C)O | 55 | 0.75 | NN.O.ONC1CCCCC12C=Nc1ccc(-c3cccc(Cl)c3)cc12>[Ni].C(C)O>NC1=Nc2ccc(-c3cccc(Cl)c3)cc2C12CCCCC2.[NH4+].[OH-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd39daf5a58f4d5c9e45cf979091f75a | COC(=O)COc1ccc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)cc1C>>Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O | O.Cl.COC(COC1=C(C=C(C=C1)SCC=C(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br)C)=O.[OH-].[Na+]>>BrC1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)Br | C[O:30][C:28]([CH2:27][O:26][c:25]1[c:2]([CH3:1])[cH:3][c:4]([S:5][CH2:6][CH:7]=[C:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]2)[cH:23][cH:24]1)=[O:29]>>[CH3:1][c:2]1[cH:3][c:4]([S:5][CH2:6][CH:7]=[C:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[c:16... | COC(=O)COc1ccc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)cc1C | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C(CSc1ccccc1)=C(c1ccccc1)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] | 93.5 | [{"value": 93.0, "product": "BrC1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.5, "product": "BrC1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (530 mg, 0.94 mmol) in ethanol (20 ml) and 1M NaOH (2.0 ml, 2.0 mmol) was stirred at room temp. for 2 h. The reaction mixture added water (20 ml) and 1N HCl (3.0 ml). The water phase was extracted with dichloromethane (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)O | null | null | COC(=O)COc1ccc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)cc1C>C(C)O>Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98105445b39e4979b24da4a8f78d2882 | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1ccccc1>>Cc1cc(SCC=C(c2ccc(-c3ccccc3)cc2)c2ccc(-c3ccccc3)cc2)ccc1OCC(=O)O | BrC1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)Br.C1(=CC=CC=C1)B(O)O.[F-].[K+].[Cl-].[NH4+]>>C1(=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 | Br[c:12]1[cH:11][cH:10][c:9]([C:8](=[CH:7][CH2:6][S:5][c:4]2[cH:3][c:2]([CH3:1])[c:35]([O:36][CH2:37][C:38](=[O:39])[OH:40])[cH:34][cH:33]2)[c:21]2[cH:13][cH:23][c:24](Br)[cH:31][cH:32]2)[cH:20][cH:19]1.OB(O)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][c:2]1[cH:3][c:4]([S:5][CH2:6][CH:7]=[C:8]([c:9]2[cH:10][cH:... | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1ccccc1 | Cc1cc(SCC=C(c2ccc(-c3ccccc3)cc2)c2ccc(-c3ccccc3)cc2)ccc1OCC(=O)O | 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].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 | C1CCOC1 | C-C Coupling | OtherReaction | f401823538ae6a41b0707d4f934f9582ed0798088e8db44163a0909a254467ad | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | C(CSc1ccccc1)=C(c1ccc(-c2ccccc2)cc1)c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](=[C:6]-[C:7])-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c;H0;D3;+0:11](-Br):[cH;D2;+0:12]:[cH;D2;+0:13]:2):[c:14]:[c:15]:1.O-B(-O)-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[C:7]-[C:6]=[C:5](-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:21]:[c:22]):[c:23]:[c:24]):[c:15]:[c... | null | [] | null | null | 1 | HOUR | In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (297 mg, 0.54 mmol), phenylboronic acid (152 mg, 1.2 mmol), KF (104 mg, 1.79 mmol), Pd2(dba)3 (30 mg, 33 mmol) and Pd(P(t-Bu)3)2 (33 mg, 65 mmol). THF (6 ml) was added to th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br-.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].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.C1CCOC1 | null | 1 | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)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].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.C1CCOC1>Cc1cc(SCC=C(c2ccc(-c3ccccc3)cc2)c2ccc(-c3ccccc3)cc... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3d87d56f4e042bca847751840000337 | CS(=O)(=O)c1ccc(B(O)O)cc1.Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O>>Cc1cc(SCC=C(c2ccc(-c3ccc(S(C)(=O)=O)cc3)cc2)c2ccc(-c3ccc(S(C)(=O)=O)cc3)cc2)ccc1OCC(=O)O | BrC1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)Br.CS(=O)(=O)C1=CC=C(C=C1)B(O)O.[F-].[K+].[Cl-].[NH4+]>>CS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)C1=CC=C(C=C1)S(=O)(=O)C | B([OH:19])([OH:20])[c:29]1[cH:30][cH:31][c:32]([S:33]([CH3:34])(=[O:35])=[O:36])[cH:37][cH:38]1.Br[c:12]1[cH:11][cH:10][c:9]([C:8](=[CH:7][CH2:6][S:5][c:4]2[cH:3][c:2]([CH3:1])[c:43]([O:44][CH2:45][C:46](=[O:47])[OH:48])[cH:42][cH:41]2)[c:25]2[cH:13][cH:39][c:28](Br)[cH:27][cH:26]2)[cH:24][cH:23]1>>[CH3:1][c:2]1[cH:3][... | CS(=O)(=O)c1ccc(B(O)O)cc1.Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O | Cc1cc(SCC=C(c2ccc(-c3ccc(S(C)(=O)=O)cc3)cc2)c2ccc(-c3ccc(S(C)(=O)=O)cc3)cc2)ccc1OCC(=O)O | 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] | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | ce56a450dd6b8f96deb02dac9a10e8b4c15b39e33b79e30a389dd2b31b0d3aa4 | 996ce2d4d4695a5c5f5489bc18374e40992c567a4c050b6407b43ea3455965ab | C(CSc1ccccc1)=C(c1ccc(-c2ccccc2)cc1)c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](=[C:6]-[C:7])-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c;H0;D3;+0:11](-Br):[cH;D2;+0:12]:[cH;D2;+0:13]:2):[c:14]:[c:15]:1.[OH;D1;+0:16]-B(-[OH;D1;+0:17])-[c;H0;D3;+0:18](:[c:19]:[c:20]):[c:21]:[c:22]>>[C:7]-[C:6]=[C:5](-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]2:[c:23]:[c:24]:[... | null | [] | null | null | 1 | HOUR | In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (208 mg, 0.38 mmol, example 1, step A–B), 4-(methansulfonyl)phenylboronic acid (280 mg, 1.4 mmol), KF (77 mg, 1.33 mmol), Pd2(dba)3 (21 mg, 23 mmol) and Pd(P(t-BU)3)2 (23 mg... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | Sulfone | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br-.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1 | null | 1 | CS(=O)(=O)c1ccc(B(O)O)cc1.Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O>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].C1CCOC1>Cc1cc(SCC=C(c2ccc(-c3ccc(S(C)(=O)=O)cc3)cc2)c2ccc(-c3ccc(S(C)(=O)=O)cc3)cc2)ccc1OCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb4c73dfe7584f60933d4cf801180706 | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1cccc(C(F)(F)F)c1.[F-]>>Cc1cc(SCC=C(c2ccc(-c3cccc(C(F)(F)F)c3)cc2)c2ccc(-c3cccc(C(F)(F)F)c3)cc2)ccc1OCC(=O)O | BrC1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)Br.FC(C=1C=C(C=CC1)B(O)O)(F)F.[F-].[K+].[Cl-].[NH4+]>>FC(C=1C=C(C=CC1)C1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)C1=CC(=CC=C1)C(F)(F)F)(F)F | Br[c:12]1[cH:11][cH:10][c:9]([C:8](=[CH:7][CH2:6][S:5][c:4]2[cH:3][c:2]([CH3:1])[c:43]([O:44][CH2:45][C:46](=[O:47])[OH:48])[cH:42][cH:41]2)[c:25]2[cH:13][cH:27][c:28](Br)[cH:39][cH:40]2)[cH:24][cH:23]1.OB(O)[c:29]1[cH:30][cH:31][cH:32][c:17]([C:18]([F:19])([F:21])[F:37])[cH:38]1.[F-:20]>>[CH3:1][c:2]1[cH:3][c:4]([S:5]... | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1cccc(C(F)(F)F)c1.[F-] | Cc1cc(SCC=C(c2ccc(-c3cccc(C(F)(F)F)c3)cc2)c2ccc(-c3cccc(C(F)(F)F)c3)cc2)ccc1OCC(=O)O | 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].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 | C1CCOC1 | C-C Coupling | OtherReaction | 02c971e011cd5a0ccf33bf84d311b8c23ca02678739a7920a6f5e84c4eebcdcd | bbcf2f366e45954510b4dc1e8f94176f116ad3092cd1991a9da7890495c35b5d | C(CSc1ccccc1)=C(c1ccc(-c2ccccc2)cc1)c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](=[C:6]-[C:7])-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c;H0;D3;+0:11](-Br):[cH;D2;+0:12]:[cH;D2;+0:13]:2):[c:14]:[c:15]:1.O-B(-O)-[c;H0;D3;+0:16]1:[c:17]:[c:18]:[cH;D2;+0:19]:[c;H0;D3;+0:20](-[C;H0;D4;+0:21](-[F;D1;H0:22])(-[F;D1;H0:23])-[F;H0;D1;+0:24]):[cH;D2;+0:25]:1.[F-;H0;D0:26]>>[... | null | [] | null | null | 1 | HOUR | In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (231 mg, 0.42 mmol, example 1, step A–B), 3-(trifluoromethyl)phenylboronic acid (203 mg, 1.1 mmol), KF (81 mg, 1.39 mmol), Pd2(dba)3 (23 mg, 25 mmol) and Pd(P(t-Bu)3)2 (26 m... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Boronic acid | Trifluoro group.Trifluoro group | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br-.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].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.C1CCOC1 | null | 1 | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1cccc(C(F)(F)F)c1.[F-]>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].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.C1CCOC1>Cc1cc(SCC=C(c2ccc(-c3cccc(C(F)(F)F)... |
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