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-ff54610c7ba349f89734c05c02f5bd56 | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)c(-c2cccs2)c1>>COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(-c2cccs2)c1 | COC1=CC(=C(C=O)C=C1)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=CC(=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1 | [CH3:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1.O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][c:20]1-[c:21]1[cH:22][cH:23][cH:24][s:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]2)[c:... | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)c(-c2cccs2)c1 | COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(-c2cccs2)c1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1ccccc1-c1cccs1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 61 | [{"value": 61.0, "product": "COC1=CC(=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-methoxy-2-thiophen-2-yl-benzaldehyde (Ex-34A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 61% yield, m.p. 209–211° C. 1H-NMR (300 MHz, d6-DMSO): 8.14 (m, 3H), 8.04 (d, 2H, J=9.2 Hz), 7.89 (d, 1H, J=15.5 Hz), 7.76 (d, 1H, J=15.5 Hz), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)c(-c2cccs2)c1>>COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(-c2cccs2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83a7ca9901c148adb3f76c7c46b13cc9 | CC(=O)c1ccccc1C(=O)O.COc1cc(OC)c(-c2cccs2)cc1C=O>>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccccc1C(=O)O | COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C(C)(=O)C1=C(C(=O)O)C=CC=C1>>COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=C(C(=O)O)C=CC=C1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26](=[O:27])[OH:28].O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14][c:15]1/[CH:16]=[CH:17]/[C:1... | CC(=O)c1ccccc1C(=O)O.COc1cc(OC)c(-c2cccs2)cc1C=O | COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccccc1C(=O)O | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 47 | [{"value": 47.0, "product": "COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=C(C(=O)O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-(thiophen-2-yl)-benzaldehyde (Ex-6A) and 2-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 47% yield, mp 196–198° C. 1H-NMR (DMSO-d6) δ 8.00 (s, 1H), 7.84 (d, 1H), 7.61 (m, 3H), 7.45 (m, 3H), 7.21 (d, 1H), 7.08 (t, 1H), 6.75 (s, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccccc1C(=O)O.COc1cc(OC)c(-c2cccs2)cc1C=O>>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccccc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b9e0aa0b4d64b108def4b32decfa04a | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1cc(OC)c(C=O)cc1Br>>COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.C(=O)(OC(C)(C)C)N1C(=CC2=CC=CC=C12)B(O)O>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)C=O)OC)OC | OB(O)[c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24].Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:26]([CH:27]=[O:28])[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2[... | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1cc(OC)c(C=O)cc1Br | COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 3b8f3e0259b4769a5826e874d5636520024cfb748a43924162932bbdf29a40ad | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3ccccc3[nH]2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:1-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20]>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:1-[C:14](=[O;D1;H0:15])-[#8... | 79 | [{"value": 79.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)C=O)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-36A: 2-(5-Formyl-2,4-dimethoxy-phenyl)-indole-1-carboxylic acid tert-butyl ester was prepared from 5-bromo-2,4-dimethoxybenzaldehyde and N-Boc-indole-2-boronic acid in a similar manner as described in Ex-3A. Yellow oil, 79% yield. 1H-NMR (CDCl3) δ 10.36 (s, 1H), 8.15 (d, J=8 Hz, 1H), 7.88 (s, 1H), 7.45 (d, J=8 Hz, 3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2ccccc2[nH]1.c1ccccc1 | c1ccccc1.c1cc2ccccc2[nH]1 | c1ccccc1.c1cc2ccccc2[nH]1 | HBr.B | null | null | null | CC(C)(C)OC(=O)n1c(B(O)O)cc2ccccc21.COc1cc(OC)c(C=O)cc1Br>>COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-557d78e808734cb58e2ddb63fd12ca6f | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)C=O)OC)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)\C=C\C(=O)C1=CC=C(C=C1)C(=O)O)OC)OC | [CH3:28][C:29](=[O:30])[c:31]1[cH:32][cH:33][c:34]([C:35](=[O:36])[OH:37])[cH:38][cH:39]1.O=[CH:27][c:26]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6]... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 8 | [{"value": 8.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)\\C=C\\C(=O)C1=CC=C(C=C1)C(=O)O)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-(5-formyl-2,4-dimethoxy-phenyl)-indole-1-carboxylic acid tert-butyl ester (Ex-36A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 8% yield, mp 182–183° C. 1H-NMR (CDCl3) δ 8.21 (d, J=8 Hz, 2H), 8.19 (d, J=13 Hz, 1H), 8.16 (d, J=7 Hz, 1H),... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cc2ccccc2[nH]1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63a936ad30604b9c91b70e45ce73f693 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(-c2cccs2)cc(OC)c1C=O>>COc1cc(-c2cccs2)cc(OC)c1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C(=CC(=C1)C=1SC=CC1)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C(=CC(=C1)C=1SC=CC1)OC)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][c:12]([O:13][CH3:14])[c:15]1/[CH:16]=[CH:17]/[C:1... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(-c2cccs2)cc(OC)c1C=O | COc1cc(-c2cccs2)cc(OC)c1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1ccc(-c2cccs2)cc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 79 | [{"value": 79.0, "product": "COC1=C(C(=CC(=C1)C=1SC=CC1)OC)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,6-dimethoxy-4-thiophen-2-yl-benzaldehyde (Ex-37A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 79% yield, m.p. 256–258° C. 1H-NMR (300 MHz, d6-DMSO): 8.11 (d, 1H, J=15.9 Hz), 8.10 (m, 4H), 8.05 (d, 1H, J=15.9 Hz), 7.73 (d, 1H, J=3.6 Hz)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(-c2cccs2)cc(OC)c1C=O>>COc1cc(-c2cccs2)cc(OC)c1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b767cccb57e4c6ca1546950b1883579 | COc1cc(OC)c(C=O)cc1Br.COc1ncc(B(O)O)c(OC)n1>>COc1ncc(-c2cc(C=O)c(OC)cc2OC)c(OC)n1 | BrC=1C(=CC(=C(C=O)C1)OC)OC.COC1=NC=C(C(=N1)OC)B(O)O>>COC1=NC=C(C(=N1)OC)C=1C(=CC(=C(C=O)C1)OC)OC | Br[c:7]1[cH:8][c:9]([CH:10]=[O:11])[c:12]([O:13][CH3:14])[cH:15][c:16]1[O:17][CH3:18].OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:22][c:19]1[O:20][CH3:21]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH:10]=[O:11])[c:12]([O:13][CH3:14])[cH:15][c:16]2[O:17][CH3:18])[c:19]([O:20][CH3:21])[n:22]1 | COc1cc(OC)c(C=O)cc1Br.COc1ncc(B(O)O)c(OC)n1 | COc1ncc(-c2cc(C=O)c(OC)cc2OC)c(OC)n1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cncnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1-[#8:15]>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1-[#8:15]):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 75 | [{"value": 75.0, "product": "COC1=NC=C(C(=N1)OC)C=1C(=CC(=C(C=O)C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-38A: 5-(2,4-Dimethoxy-pyrimidin-5-yl)-2,4-dimethoxy-benzaldehyde was prepared from 5-bromo-2,4-dimethoxybenzaldehyde and 2,4-Dimethoxy-pyrimidin-5-boronic acid in a similar manner as described in Ex-3A, 75% yield. 1H-NMR (CDCl3) δ 10.34 (s, 1H), 8.13 (s, 1H), 7.74 (s, 1H), 6.51 (s, 1H), 4.03 (s, 3H), 3.99 (s, 3H), 3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr.B | null | null | null | COc1cc(OC)c(C=O)cc1Br.COc1ncc(B(O)O)c(OC)n1>>COc1ncc(-c2cc(C=O)c(OC)cc2OC)c(OC)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6a7cf4d22174393ae1bd42943b2db83 | CC(=O)c1ccc(C(=O)O)cc1.COc1ncc(-c2cc(C=O)c(OC)cc2OC)c(OC)n1>>COc1ncc(-c2cc(/C=C/C(=O)c3ccc(C(=O)O)cc3)c(OC)cc2OC)c(OC)n1 | COC1=NC=C(C(=N1)OC)C=1C(=CC(=C(C=O)C1)OC)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=NC=C(C(=N1)OC)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC | [CH3:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]1.O=[CH:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][n:4][c:3]([O:2][CH3:1])[n:33][c:30]2[O:31][CH3:32])[c:27]([O:28][CH3:29])[cH:26][c:23]1[O:24][CH3:25]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][c:9](/[CH:10]=[CH:11]/[C:12](=[O:13])... | CC(=O)c1ccc(C(=O)O)cc1.COc1ncc(-c2cc(C=O)c(OC)cc2OC)c(OC)n1 | COc1ncc(-c2cc(/C=C/C(=O)c3ccc(C(=O)O)cc3)c(OC)cc2OC)c(OC)n1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cncnc2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 22 | [{"value": 22.0, "product": "COC1=NC=C(C(=N1)OC)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 5-(2,4-dimethoxy-pyrimidin-5-yl)-2,4-dimethoxy-benzaldehyde (Ex-38A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 203–205° C., 22% yield. 1H-NMR (DMSO-d6) δ 8.11–9.15 (m, 3H), 7.99–8.06 (m, 3H), 7.88 (s, 1H), 7.76 (d, J=17 Hz, 1H), 6.7... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1ncc(-c2cc(C=O)c(OC)cc2OC)c(OC)n1>>COc1ncc(-c2cc(/C=C/C(=O)c3ccc(C(=O)O)cc3)c(OC)cc2OC)c(OC)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d29e144585dc4ce4b0a63e3261237b63 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(C=O)c(-c2cccs2)c1>>COc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(-c2cccs2)c1 | COC1=C(C=O)C(=CC(=C1)OC)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C(=CC(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21]1.O=[CH:9][c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:28][c:22]1-[c:23]1[cH:24][cH:25][cH:26][s:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](/[CH:9]=[CH:10]/[C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([C:17](=[O:1... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(C=O)c(-c2cccs2)c1 | COc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(-c2cccs2)c1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1ccccc1-c1cccs1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 61 | [{"value": 61.0, "product": "COC1=C(C(=CC(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-6-thiophen-2-yl-benzaldehyde (Ex-39A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 61% yield, mp 231° C. (dec.). 1H-NMR (DMSO-d6) δ 8.02 (d, 2H), 7.93 (d, 2H), 7.73 (m, 3H), 7.15 (t, 1H), 7.07 (d, 1H), 6.72 (d, 1H), 6.62 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(C=O)c(-c2cccs2)c1>>COc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(-c2cccs2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd0ec8ebfe9741fe8411348cbbc1cf68 | COc1cc(OC)c(C=O)cc1Br.Cc1ccc(B(O)O)s1>>COc1cc(OC)c(-c2ccc(C)s2)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.CC1=CC=C(S1)B(O)O>>COC1=C(C=O)C=C(C(=C1)OC)C=1SC(=CC1)C | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:16]([CH:17]=[O:18])[cH:15]1.OB(O)[c:9]1[cH:10][cH:11][c:12]([CH3:13])[s:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[s:14]2)[cH:15][c:16]1[CH:17]=[O:18] | COc1cc(OC)c(C=O)cc1Br.Cc1ccc(B(O)O)s1 | COc1cc(OC)c(-c2ccc(C)s2)cc1C=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 100 | [{"value": 100.0, "product": "COC1=C(C=O)C=C(C(=C1)OC)C=1SC(=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-40A: 2,4-Dimethoxy-5-(5-methyl-thiophen-2-yl)-benzaldehyde was prepared from 5-bromo-2,4-dimethoxybenzaldehyde and 5-methyl-thiophene-2-boronic acid in a similar manner as described in Ex-3A, 100% yield. 1H-NMR (CDCl3) δ 10.33 (s, 1H), 8.05 (s, 1H), 7.22 (d, J=4 Hz, 1H), 6.72 (d, J=4 Hz, 1H), 6.49 (s, 1H), 4.00 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | null | null | null | COc1cc(OC)c(C=O)cc1Br.Cc1ccc(B(O)O)s1>>COc1cc(OC)c(-c2ccc(C)s2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc3607815f2b4883b3402850fcc9a9b9 | COc1ccc(C=O)cc1Br.OB(O)c1cccs1>>COc1ccc(C=O)cc1-c1cccs1 | BrC=1C=C(C=O)C=CC1OC.S1C(=CC=C1)B(O)O>>COC1=C(C=C(C=O)C=C1)C=1SC=CC1 | Br[c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9]1.OB(O)[c:11]1[cH:12][cH:13][cH:14][s:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][s:15]1 | COc1ccc(C=O)cc1Br.OB(O)c1cccs1 | COc1ccc(C=O)cc1-c1cccs1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 96 | [{"value": 96.0, "product": "COC1=C(C=C(C=O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-41A: 4-Methoxy-3-(thiophen-2-yl)-benzaldehyde was prepared from 3-bromo-4-methoxybenzaldehyde and thiophene-2-boronic acid in a similar manner as described in Ex-3A. Orange oil, 96% yield. 1H-NMR (CDCl3) δ 9.94 (s, 1H), 8.16 (d, J=1.8 Hz, 1H), 7.80 (dd, J=2.4, 8.4 Hz, 1H), 7.57 (dd, J=1.8, 3.6 Hz, 1H), 7.38 (d, J=5.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | null | null | null | COc1ccc(C=O)cc1Br.OB(O)c1cccs1>>COc1ccc(C=O)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79ad8c8494d648dc961f12a17f084d9f | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)cc1-c1cccs1>>COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | COC1=C(C=C(C=O)C=C1)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1 | [CH3:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1.O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21](-[c:22]2[cH:23][cH:24][cH:25][s:26]2)[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]2)[... | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)cc1-c1cccs1 | COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 71 | [{"value": 71.0, "product": "COC1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-methoxy-3-(thiophen-2-yl)-benzaldehyde (Ex-41A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 219–220° C., 71% yield. 1H-NMR (DMSO-D6) δ 13.36 (br s, 1H), 8.25–8.31 (m, 3H), 8.11 (d, J=8 Hz, 2H), 7.85–7.98 (m, 3H), 7.78–7.80 (m, 1H), ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)cc1-c1cccs1>>COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6f3fe07db1a4753bd3cd731735780b8 | O=Cc1cccc(Br)c1.OB(O)c1cccs1>>O=Cc1cccc(-c2cccs2)c1 | BrC=1C=C(C=O)C=CC1.S1C(=CC=C1)B(O)O>>S1C(=CC=C1)C=1C=C(C=O)C=CC1 | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:13]1.OB(O)[c:8]1[cH:9][cH:10][cH:11][s:12]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[cH:13]1 | O=Cc1cccc(Br)c1.OB(O)c1cccs1 | O=Cc1cccc(-c2cccs2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1):[c:6]:[c:7] | 93 | [{"value": 93.0, "product": "S1C(=CC=C1)C=1C=C(C=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-42A: 3-(Thiophen-2-yl)-benzaldehyde was prepared from 3-bromobenzaldehyde and thiophene-2-boronic acid in a similar manner as described in Ex-3A. Orange oil, 93% yield. 1H-NMR (CDCl3) δ 10.06 (s, 1H), 8.10 (s, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.78 (d, J=7.2 Hz, 1H), 7.55 (dd, J=7.2, 8.4 Hz, 1H), 7.40 (dd, J=1.5, 3.6 Hz,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | null | null | null | O=Cc1cccc(Br)c1.OB(O)c1cccs1>>O=Cc1cccc(-c2cccs2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12ec378e0f82417390911f19266aae37 | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1cccc(-c2cccs2)c1>>O=C(O)c1ccc(C(=O)/C=C/c2cccc(-c3cccs3)c2)cc1 | S1C(=CC=C1)C=1C=C(C=O)C=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>S1C(=CC=C1)C=1C=C(C=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH3:10])[cH:23][cH:24]1.O=[CH:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][s:21]2)[cH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])/[CH:10]=[CH:11]/[c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][s:21]3)[cH... | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1cccc(-c2cccs2)c1 | O=C(O)c1ccc(C(=O)/C=C/c2cccc(-c3cccs3)c2)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 71 | [{"value": 71.0, "product": "S1C(=CC=C1)C=1C=C(C=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 3-(thiophen-2-yl)-benzaldehyde (Ex-42A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 238° C. (dec), 71% yield. 1H-NMR (DMSO-D6) δ 13.40 (bs, 1H), 8.29 (d, J=8 Hz, 2H), 8.22 (s, 1H), 8.13 (d, J=8 Hz, 2H), 8.04 (s, 1H), 7.87 (s, 1H), 7.8... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1cccc(-c2cccs2)c1>>O=C(O)c1ccc(C(=O)/C=C/c2cccc(-c3cccs3)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e3bb6c43f89f4a48b1f3998f4095d6e4 | CC(=O)c1cccc(C(=O)O)c1.COc1cc(OC)c(-c2cccs2)cc1C=O>>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1cccc(C(=O)O)c1 | COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C(C)(=O)C=1C=C(C(=O)O)C=CC1>>COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C=1C=C(C(=O)O)C=CC1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14][c:15]1/[CH:16]=[CH:17]/[C... | CC(=O)c1cccc(C(=O)O)c1.COc1cc(OC)c(-c2cccs2)cc1C=O | COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1cccc(C(=O)O)c1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 65 | [{"value": 65.0, "product": "COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C=1C=C(C(=O)O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-(thiophen-2-yl)-benzaldehyde (Ex-6A) and 3-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 65% yield, mp 179–182° C. 1H-NMR (DMSO-d6) δ 8.54 (s, 1H), 8.39 (d, 1H), 8.25 (s, 1H), 8.15 (d, 1H), 8.04 (d, 1H), 7.90 (d, 1H), 7.67 (m, 2H... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1cccc(C(=O)O)c1.COc1cc(OC)c(-c2cccs2)cc1C=O>>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1cccc(C(=O)O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7070a2403dc04cfaa55f901c61e6fa83 | CI.COc1ccc(C=O)c(O)c1-c1cc2ccccc2s1>>COc1ccc(C=O)c(OC)c1-c1cc2ccccc2s1 | S1C2=C(C=C1C=1C(=C(C=O)C=CC1OC)O)C=CC=C2.C([O-])([O-])=O.[K+].[K+].CI>>S1C2=C(C=C1C=1C(=C(C=O)C=CC1OC)OC)C=CC=C2 | I[CH3:11].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([OH:10])[c:12]1-[c:13]1[cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[s:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([O:10][CH3:11])[c:12]1-[c:13]1[cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[s:21]1 | CI.COc1ccc(C=O)c(O)c1-c1cc2ccccc2s1 | COc1ccc(C=O)c(OC)c1-c1cc2ccccc2s1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(-c2cc3ccccc3s2)cc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[CH3;D1;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-[C:3]=[O;D1;H0:2] | 97.1 | [{"value": 97.0, "product": "S1C2=C(C=C1C=1C(=C(C=O)C=CC1OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "S1C2=C(C=C1C=1C(=C(C=O)C=CC1OC)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-44B: 3-Benzo[b]thiophen-2-yl-2-hydroxy-4-methoxy-benzaldehyde (Ex-44A, 57.4 mg, 0.202 mmol) was dissolved in acetone (5 mL) and potassium carbonate (31 mg, 0.22 mmol) was added. Methyl iodide (25 uL, 0.40 mmol) was added and the solution was heated to reflux for 3.5 h. After cooling, the crude reaction mix was conce... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2sccc2c1 | HI | CC(=O)C | null | null | CI.COc1ccc(C=O)c(O)c1-c1cc2ccccc2s1>CC(=O)C>COc1ccc(C=O)c(OC)c1-c1cc2ccccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b003aa407c8c4f929c308d4ff24f7600 | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)c(OC)c1-c1cc2ccccc2s1>>COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(OC)c1-c1cc2ccccc2s1 | S1C2=C(C=C1C=1C(=C(C=O)C=CC1OC)OC)C=CC=C2.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>S1C2=C(C=C1C=1C(=C(C=CC1OC)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)C=CC=C2 | [CH3:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1.O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:23](-[c:24]2[cH:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]3[s:32]2)[c:20]1[O:21][CH3:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]... | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)c(OC)c1-c1cc2ccccc2s1 | COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(OC)c1-c1cc2ccccc2s1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 64 | [{"value": 64.0, "product": "S1C2=C(C=C1C=1C(=C(C=CC1OC)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 3-benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde (Ex-44B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 237° C. (dec.), 64% yield. 1H-NMR (DMSO-d6) δ 13.37 (bs, 1H), 8.20–8.25 (m, 3H), 8.11 (d, J=8 Hz, 2H), 8.02 (d, J=8 Hz, 1H), 7.96 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccc2sccc2c1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(C=O)c(OC)c1-c1cc2ccccc2s1>>COc1ccc(/C=C/C(=O)c2ccc(C(=O)O)cc2)c(OC)c1-c1cc2ccccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a18fe35f3b5c46aaa2906acb46b62369 | COc1ccc(Br)cc1C=O.OB(O)c1cccs1>>COc1ccc(-c2cccs2)cc1C=O | BrC=1C=CC(=C(C=O)C1)OC.S1C(=CC=C1)B(O)O>>COC1=C(C=O)C=C(C=C1)C=1SC=CC1 | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:13]([CH:14]=[O:15])[cH:12]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][s:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[cH:12][c:13]1[CH:14]=[O:15] | COc1ccc(Br)cc1C=O.OB(O)c1cccs1 | COc1ccc(-c2cccs2)cc1C=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1):[c:6]:[c:7] | null | [] | null | null | null | null | Ex-45A: 2-Methoxy-5-(thiophen-2-yl)-benzaldehyde was prepared from 5-bromo-2-methoxybenzaldehyde and thiophene-2-boronic acid in a similar manner as described in Ex-3A. 1H NMR (CDCl3) δ 10.49 (s, 1H), 8.07 (d, J=3 Hz, 1H), 7.79 (dd, J=3, 9.0 Hz, 1H), 7.28–7.26 (m, 2H), 7.09–7.06 (m, 1H), 7.02 (d, J=9 Hz, 1H), 3.97 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | null | null | null | COc1ccc(Br)cc1C=O.OB(O)c1cccs1>>COc1ccc(-c2cccs2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed732168b13e402cab606e79ec750a34 | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(-c2cccs2)cc1C=O>>COc1ccc(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C=C(C=C1)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C=C1)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1.O=[CH:14][c:13]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[cH:12][c:13]1/[CH:14]=[CH:15]/[C:16](=[O:17])[c:18]1[cH:19][cH... | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(-c2cccs2)cc1C=O | COc1ccc(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 2-methoxy-5-(thiophen-2-yl)-benzaldehyde (Ex-45A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 195–196° C. 1H-NMR (DMSO-d6) δ 8.23–8.20 (m, 3H), 8.08–7.96 (m, 4H), 7.67 (dd, J=2.1, 6.8 Hz, 1H), 7.55 (d, J=3.8 Hz, 1H), 7.49 (d, J=5.1 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1ccc(-c2cccs2)cc1C=O>>COc1ccc(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e624bf1f72147079f9c2ca4a68268e2 | COc1cc(OC)c(C=O)cc1Br.OCCO>>COc1cc(OC)c(C2OCCO2)cc1Br | BrC=1C(=CC(=C(C=O)C1)OC)OC.C(CO)O>>BrC=1C(=CC(=C(C1)C1OCCO1)OC)OC | O=[CH:9][c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:15]([Br:16])[cH:14]1.[OH:10][CH2:11][CH2:12][OH:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]2[O:10][CH2:11][CH2:12][O:13]2)[cH:14][c:15]1[Br:16] | COc1cc(OC)c(C=O)cc1Br.OCCO | COc1cc(OC)c(C2OCCO2)cc1Br | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc(C2OCCO2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[c:3]:[c:2](-[CH;D3;+0:1]1-[O;H0;D2;+0:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-1):[c:4] | 92 | [{"value": 92.0, "product": "BrC=1C(=CC(=C(C1)C1OCCO1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "BrC=1C(=CC(=C(C1)C1OCCO1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Ex-46A: 5-Bromo-2,4-dimethoxybenzaldehyde (4.92 g, 20.1 mmol) was dissolved in benzene (41 mL). Ethylene glycol (3 mL, 54 mmol) and p-toluenesulfonic acid (25 mg, 0.13 mmol) were added and the solution was refluxed with a Dean-Stark trap attached. After 6 h, the reaction was cooled and washed with water (1×20 mL), satu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccccc1.C1COCO1 | HO- | C1(=CC=C(C=C1)S(=O)(=O)O)C.C1=CC=CC=C1 | null | 6 | COc1cc(OC)c(C=O)cc1Br.OCCO>C1(=CC=C(C=C1)S(=O)(=O)O)C.C1=CC=CC=C1>COc1cc(OC)c(C2OCCO2)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71cc95bcc694456f8188c5073823441d | CC1(C)OBOC1(C)C.COc1cc(OC)c(C2OCCO2)cc1Br>>COc1cc(OC)c(C2OCCO2)cc1B1OC(C)(C)C(C)(C)O1 | CC1(OBOC1(C)C)C.[NH4+].[Cl-].BrC=1C(=CC(=C(C1)C1OCCO1)OC)OC.CCN(CC)CC.C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1>>O1C(OCC1)C=1C(=CC(=C(C1)B1OC(C(O1)(C)C)(C)C)OC)OC | [BH:16]1[O:17][C:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[O:24]1.Br[c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]2[O:10][CH2:11][CH2:12][O:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]2[O:10][CH2:11][CH2:12][O:13]2)[cH:14][c:15]1[B:16]1[O:17][C:18]([CH3:19])([CH3:20])[... | CC1(C)OBOC1(C)C.COc1cc(OC)c(C2OCCO2)cc1Br | COc1cc(OC)c(C2OCCO2)cc1B1OC(C)(C)C(C)(C)O1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | O.O1CCOCC1 | Miscellaneous | OtherReaction | ad2870ebdd035b36ca28b76fce8ec2fa1001820252a6151877804f04f83d958c | f1d1202adfbfb63cdbea2fa31eb5766b49914acb653b77a04e8043b460a99de7 | c1cc(B2OCCO2)cc(C2OCCO2)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[#8:7]1-[BH;D2;+0:8]-[#8:9]-[C:10]-[C:11]-1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[B;H0;D3;+0:8]1-[#8:7]-[C:11]-[C:10]-[#8:9]-1):[c:2]:[c:3] | 92.6 | [{"value": 59.0, "product": "O1C(OCC1)C=1C(=CC(=C(C1)B1OC(C(O1)(C)C)(C)C)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "O1C(OCC1)C=1C(=CC(=C(C1)B1OC(C(O1)(C)C)(C)C)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-46B: 2-(5-Bromo-2,4-dimethoxy-phenyl)-[1,3]dioxolane (Ex-46A, 4.78 g, 10.5 mmol) was dissolved in dioxane (75 mL) and the solution was purged with nitrogen for 15 min. Pd(OAc)2 (188 mg, 0.84 mmol), Et3N (6.91 mL, 49.6 mmol), and 2-(dicyclohexylphosphino)biphenyl (1.16 g, 3.31 mmol) were added. 4,4,5,5-Tetramethyl-[1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic ester | B1OCCO1.c1ccccc1 | c1ccccc1.[B]1OCCO1 | c1ccccc1.C1COCO1.[B]1OCCO1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].O.O1CCOCC1 | null | null | CC1(C)OBOC1(C)C.COc1cc(OC)c(C2OCCO2)cc1Br>CC(=O)[O-].CC(=O)[O-].[Pd+2].O.O1CCOCC1>COc1cc(OC)c(C2OCCO2)cc1B1OC(C)(C)C(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c1ac17fdab24ec4b251ad30815eb2e7 | COc1cc(OC)c(C2OCCO2)cc1B1OC(C)(C)C(C)(C)O1.Ic1cnccn1>>COc1cc(OC)c(C2OCCO2)cc1-c1cnccn1 | O.IC1=NC=CN=C1.O1C(OCC1)C=1C(=CC(=C(C1)B1OC(C(O1)(C)C)(C)C)OC)OC.C(=O)([O-])[O-].[Na+].[Na+]>>O1C(OCC1)C=1C(=CC(=C(C1)C1=NC=CN=C1)OC)OC | CC1(C)OB([c:15]2[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]3[O:10][CH2:11][CH2:12][O:13]3)[cH:14]2)OC1(C)C.I[c:16]1[cH:17][n:18][cH:19][cH:20][n:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]2[O:10][CH2:11][CH2:12][O:13]2)[cH:14][c:15]1-[c:16]1[cH:17][n:18][cH:19][cH:20][n:21]1 | COc1cc(OC)c(C2OCCO2)cc1B1OC(C)(C)C(C)(C)O1.Ic1cnccn1 | COc1cc(OC)c(C2OCCO2)cc1-c1cnccn1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic esters | 0c589f4e5cd4c264cb91d66c2bd633ae3113d711184c5ffd904f0f28325257ba | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1cc(-c2cnccn2)cc(C2OCCO2)c1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6])-O-C-1(-C)-C.I-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1):[c:2]:[c:3] | 59 | [{"value": 59.0, "product": "O1C(OCC1)C=1C(=CC(=C(C1)C1=NC=CN=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.0, "product": "O1C(OCC1)C=1C(=CC(=C(C1)C1=NC=CN=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-46C: 2-(5-[1.3]Dioxolan-2-yl-2,4-dimethoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Ex-46B, 2.22 g, 6.60 mmol, containing borolane impurity) was dissolved in DME (60 mL) and 2-iodopyrazine (0.59 mL, 6.0 mmol) was added. 2M aqueous Na2CO3 (17.8 mL, 35.6 mmol) was added and the mixture was purged with nitroge... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1cnccn1 | c1ccccc1.c1cnccn1 | c1ccccc1.C1COCO1.c1cnccn1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | null | COc1cc(OC)c(C2OCCO2)cc1B1OC(C)(C)C(C)(C)O1.Ic1cnccn1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>COc1cc(OC)c(C2OCCO2)cc1-c1cnccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d427d4fef5b1445cbb0a32b5034db457 | COc1cc(OC)c(C2OCCO2)cc1-c1cnccn1>>COc1cc(OC)c(-c2cnccn2)cc1C=O | O1C(OCC1)C=1C(=CC(=C(C1)C1=NC=CN=C1)OC)OC.C1(=CC=C(C=C1)S(=O)(=O)O)C.O>>COC1=C(C=O)C=C(C(=C1)OC)C1=NC=CN=C1 | C1C[O:18][CH:17]([c:8]2[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:16](-[c:9]3[cH:10][n:11][cH:12][cH:13][n:14]3)[cH:15]2)O1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][n:14]2)[cH:15][c:16]1[CH:17]=[O:18] | COc1cc(OC)c(C2OCCO2)cc1-c1cnccn1 | COc1cc(OC)c(-c2cnccn2)cc1C=O | null | null | CC(=O)C | Miscellaneous | Acetal hydrolysis to aldehyde | ae771f16810464bcd41bf8cabda93aa9d8fe75f24ddd76bdf1ab2ea57c8b8018 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(-c2cnccn2)cc1 | [#8:1]-[c:2]1:[c:3]:[c:4](-[#8:5]):[c;H0;D3;+0:6](-[CH;D3;+0:7]2-O-C-C-[O;H0;D2;+0:8]-2):[c:9]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:[c:16]:1>>[#8:1]-[c:2]1:[c:3]:[c:4](-[#8:5]):[c;H0;D3;+0:6](-[c;H0;D3;+0:11]2:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]:[c:16]:2):[c:9]:[c;H0;D3;+0:10]:1-[CH;D2;+0:... | 34.7 | [{"value": 18.0, "product": "COC1=C(C=O)C=C(C(=C1)OC)C1=NC=CN=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.7, "product": "COC1=C(C=O)C=C(C(=C1)OC)C1=NC=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Ex-46D: 2-(5-[1,3]Dioxolan-2-yl-2,4-dimethoxy-phenyl)-pyrazine (1.02 g, 3.54 mmol) was dissolved in acetone and p-toluenesulfonic acid (100 mg, 0.53 mmol) and water (5 mL) were added. The solution was stirred for 3 h at room temperature, then concentrated on the rotavap. The resulting mixture was diluted with water (50... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1.c1ccccc1.c1cnccn1 | c1ccccc1.c1cnccn1 | c1ccccc1.c1cnccn1 | HO- | CC(=O)C | null | 3 | COc1cc(OC)c(C2OCCO2)cc1-c1cnccn1>CC(=O)C>COc1cc(OC)c(-c2cnccn2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d29afc52a2eb4b238f71e3c3b023b557 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cnccn2)cc1C=O>>COc1cc(OC)c(-c2cnccn2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C=C(C(=C1)OC)C1=NC=CN=C1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C(=C1)OC)C1=NC=CN=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29]1.O=[CH:17][c:16]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][n:14]2)[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][n:14]2)[cH:15][c:16]1/[CH:17... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cnccn2)cc1C=O | COc1cc(OC)c(-c2cnccn2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cnccn2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 4 | [{"value": 4.0, "product": "COC1=C(C=C(C(=C1)OC)C1=NC=CN=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-pyrazin-2-yl-benzaldehyde (Ex-46D) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 238° C. (dec.), 4% yield. 1H-NMR (DMSO-D6) δ 9.04 (d, J=2 Hz, 1H), 8.75–8.76 (m, 1H), 8.56 (d, J=2 Hz, 1H), 8.32 (s, 1H), 8.19 (d, J=9 Hz, ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cnccn1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cnccn2)cc1C=O>>COc1cc(OC)c(-c2cnccn2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b3481fc3ecd4b3fb4bb59977d601a95 | CCOC(=O)C(C)(C)Oc1cc(OC)c(C=O)cc1-c1cccs1>>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O | C(C)OC(C(C)(C)OC1=C(C=C(C(=C1)OC)C=O)C=1SC=CC1)=O.CO.[OH-].[Li+]>>C(=O)C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1 | CC[O:12][C:10]([C:7]([O:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]([CH:21]=[O:22])[cH:19][c:13]1-[c:14]1[cH:15][cH:16][cH:17][s:18]1)([CH3:8])[CH3:9])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:19][c:20]1[CH:21]=[O:22] | CCOC(=O)C(C)(C)Oc1cc(OC)c(C=O)cc1-c1cccs1 | COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O | null | null | O.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cccs2)cc1 | C-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] | 87 | [{"value": 87.0, "product": "C(=O)C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.9, "product": "C(=O)C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Ex-47D: To a solution of 2-(4-formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid ethyl ester (0.29 g, 0.83 mmol) in a mixture of tetrahydrofuran, water and methanol (9 mL, 4:1:1) was added lithium hydroxide (0.10 g, 2.49 mmol) and the resulting yellow slurry was stirred at rt for 5 h. The mixture was dil... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccsc1 | Other | O.O1CCCC1 | null | 5 | CCOC(=O)C(C)(C)Oc1cc(OC)c(C=O)cc1-c1cccs1>O.O1CCCC1>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92412a7fd2494c52aa9756f44c45fa54 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O>>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | Cl.C(=O)C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1.C[O-].[Li+]>>C(=O)(O)C(C)(OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)C | [CH3:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([C:29](=[O:30])[OH:31])[cH:32][cH:33]1.O=[CH:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:1... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O | COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | O.CN(C=O)C.CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "C(=O)(O)C(C)(OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "C(=O)(O)C(C)(OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 2-(4-Formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-47, 0.23 g, 0.72 mmol) and 4-acetylbenzoic acid (0.12 g, 0.72 mmol) were dissolved in a dimethylformamide-methanol solution (5 mL, 7:3). After complete dissolution, lithium methoxide (0.11 g, 2.9 mmol) was added and the resulting orange slurry w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | O.CN(C=O)C.CO | null | 4 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O>O.CN(C=O)C.CO>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-763725ebc57e427ab20c04902207ecc0 | CC(=O)c1ccccc1C(=O)O.COc1ccc(C=O)cc1-c1cccs1>>COc1ccc(/C=C/C(=O)c2ccccc2C(=O)O)cc1-c1cccs1 | COC1=C(C=C(C=O)C=C1)C=1SC=CC1.C(C)(=O)C1=C(C(=O)O)C=CC=C1>>COC1=C(C=C(C=C1)/C=C/C(=O)C1=C(C(=O)O)C=CC=C1)C=1SC=CC1 | [CH3:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17](=[O:18])[OH:19].O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21](-[c:22]2[cH:23][cH:24][cH:25][s:26]2)[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17](=[O:18])[OH:19])[cH:2... | CC(=O)c1ccccc1C(=O)O.COc1ccc(C=O)cc1-c1cccs1 | COc1ccc(/C=C/C(=O)c2ccccc2C(=O)O)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 44 | [{"value": 44.0, "product": "COC1=C(C=C(C=C1)/C=C/C(=O)C1=C(C(=O)O)C=CC=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-methoxy-3-(thiophen-2-yl)-benzaldehyde (Ex-41A) and 2-acetylbenzoic acid in a similar manner as described in Ex-3. Beige solid with green tint, mp 79–81° C., 44% yield. 1H-NMR (DMSO-D6) δ 8.07 (d, J=2 Hz, 1H), 7.91 (d, J=8 Hz, 1H), 7.73 (dd, J=2, 4 Hz, 1H), 7.67–7.70 (m, ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccccc1C(=O)O.COc1ccc(C=O)cc1-c1cccs1>>COc1ccc(/C=C/C(=O)c2ccccc2C(=O)O)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e909956e834c433c90c3f67ce454f373 | CC(=O)c1ccc(C(=O)O)cc1.COCCOCCOc1cc(OC)c(C=O)cc1-c1cccs1>>COCCOCCOc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | COC1=C(C=O)C=C(C(=C1)OCCOCCOC)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C(=C1)OCCOCCOC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([C:23](=[O:24])[OH:25])[cH:26][cH:27]1.O=[CH:15][c:14]1[c:11]([O:12][CH3:13])[cH:10][c:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:29](-[c:30]2[cH:31][cH:32][cH:33][s:34]2)[cH:28]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]([O:1... | CC(=O)c1ccc(C(=O)O)cc1.COCCOCCOc1cc(OC)c(C=O)cc1-c1cccs1 | COCCOCCOc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 61 | [{"value": 61.0, "product": "COC1=C(C=C(C(=C1)OCCOCCOC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-methoxy-4-[2-(2-methoxy-ethoxy)-ethoxy]-5-thiophen-2-yl-benzaldehyde (Ex-49A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 174–175° C., 61% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.23 (d, 2H, J=8.1 Hz), 8.05–8.11 (m, 3H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COCCOCCOc1cc(OC)c(C=O)cc1-c1cccs1>>COCCOCCOc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ea7adcba54e488794a8fbab596dfcd5 | CC(C)(C)[SiH2]OC(C)(C)C(CO)CO[Si](C)(C)C(C)(C)C.CS(=O)(=O)Cl>>CC(C)(C)[SiH2]OC(C)(C)C(CO[Si](C)(C)C(C)(C)C)COS(C)(=O)=O | C(C)(C)(C)[Si](OCC(CO)C(O[SiH2]C(C)(C)C)(C)C)(C)C.C(C)N(CC)CC.S(=O)(=O)(C)Cl>>C(C)(C)(C)[Si](OCC(COS(=O)(=O)C)C(O[SiH2]C(C)(C)C)(C)C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[CH:10]([CH2:11][O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][OH:21].Cl[S:22]([CH3:23])(=[O:24])=[O:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[CH:10]([CH2:11][O:12][Si:13]([CH3:14])([CH3:15])[C:... | CC(C)(C)[SiH2]OC(C)(C)C(CO)CO[Si](C)(C)C(C)(C)C.CS(=O)(=O)Cl | CC(C)(C)[SiH2]OC(C)(C)C(CO[Si](C)(C)C(C)(C)C)COS(C)(=O)=O | null | null | ClCCl.O.C(C)(=O)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 97 | [{"value": 97.0, "product": "C(C)(C)(C)[Si](OCC(COS(=O)(=O)C)C(O[SiH2]C(C)(C)C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.2, "product": "C(C)(C)(C)[Si](OCC(COS(=O)(=O)C)C(O[SiH2]C(C)(C)C)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Ex-50A: To a solution of 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propan-1-ol (25.0 g, 74.3 mmol) and triethylamine (22.6 g, 223 mmol) in dichloromethane (150 mL) at 0° C. was added mesyl chloride (12.8 g, 111 mmol) and the resulting slurry was stirred at 0° C. for 15 min and allowed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | ClCCl.O.C(C)(=O)OCC | 0 | 0.25 | CC(C)(C)[SiH2]OC(C)(C)C(CO)CO[Si](C)(C)C(C)(C)C.CS(=O)(=O)Cl>ClCCl.O.C(C)(=O)OCC>CC(C)(C)[SiH2]OC(C)(C)C(CO[Si](C)(C)C(C)(C)C)COS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8570f67ca7124b17bf34e012aef4aeb0 | COc1cc(OCC(CO[Si](C)(C)C(C)(C)C)C(C)(C)O[SiH2]C(C)(C)C)c(-c2cccs2)cc1C=O>>COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O | C(C)(C)(C)[Si](OCC(COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC)C(O[SiH2]C(C)(C)C)(C)C)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OCC(COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC)CO | CC(C)(C)[SiH2][O:12][C:11](C)(C)[CH:8]([CH2:7][O:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]([CH:21]=[O:22])[cH:19][c:13]1-[c:14]1[cH:15][cH:16][cH:17][s:18]1)[CH2:9][O:10][Si](C)(C)C(C)(C)C>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][OH:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:19][... | COc1cc(OCC(CO[Si](C)(C)C(C)(C)C)C(C)(C)O[SiH2]C(C)(C)C)c(-c2cccs2)cc1C=O | COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O | null | null | C(C)(=O)OCC.O1CCCC1 | Deprotection | OtherReaction | 172fccab2c64516642d661e8d39a05ea0f9e6e58ad38da441d588e65afa31a79 | 268e221542777e4e8d0f52b07a5def6279d4e8811062d062d45975490c54a487 | c1ccc(-c2cccs2)cc1 | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C)(-C)-[C:3](-[C:4])-[C:5]-[O;H0;D2;+0:6]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:4]-[C:3](-[C:5]-[OH;D1;+0:6])-[CH2;D2;+0:2]-[OH;D1;+0:1] | 99 | [{"value": 99.0, "product": "OCC(COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "OCC(COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Ex-50C: To a solution of 4-[3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propoxy]-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-50B, 0.78 g, 1.41 mmol) in tetrahydrofuran (5 mL) was added tetrabutylammonium fluoride (1 M in tetrahydrofuran, 3.0 mL, 2.9 mmol) and the mixture was stirred at rt... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol.Primary alcohol | null | null | c1ccccc1.c1ccsc1 | Other | C(C)(=O)OCC.O1CCCC1 | null | 0.5 | COc1cc(OCC(CO[Si](C)(C)C(C)(C)C)C(C)(C)O[SiH2]C(C)(C)C)c(-c2cccs2)cc1C=O>C(C)(=O)OCC.O1CCCC1>COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4babb9353b6d49c6ab4aa994636ddddb | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O>>COc1cc(OCC(CO)CO)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | OCC(COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC)CO.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>OCC(COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)CO | [CH3:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([C:29](=[O:30])[OH:31])[cH:32][cH:33]1.O=[CH:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][OH:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][OH:12]... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O | COc1cc(OCC(CO)CO)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 60 | [{"value": 60.0, "product": "OCC(COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-(3-hydroxy-2-hydroxymethyl-propoxy)-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-50C) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 199–201° C., 60% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.23 (d, 2H, J=8.7 Hz), 8.06–8.11 (m, ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O>>COc1cc(OCC(CO)CO)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71986f3dc47b45d791832c7efeb6f0ef | CC(=O)c1ccc(C(=O)O)cc1.CCOc1cc(OC)c(C=O)cc1-c1cccs1>>CCOc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | C(C)OC1=CC(=C(C=O)C=C1C=1SC=CC1)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>C(C)OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC | [CH3:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]1.O=[CH:10][c:9]1[c:6]([O:7][CH3:8])[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:24](-[c:25]2[cH:26][cH:27][cH:28][s:29]2)[cH:23]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([O:7][CH3:8])[c:9](/[CH:10]=[CH:11]/[C:12](=[O:13])[c:14]2[cH:15][cH:16][... | CC(=O)c1ccc(C(=O)O)cc1.CCOc1cc(OC)c(C=O)cc1-c1cccs1 | CCOc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 76 | [{"value": 76.0, "product": "C(C)OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-ethoxy-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-53A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 210–212° C., 76% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.23 (d, 2H, J=9.0 Hz), 8.06–8.11 (m, 3H), 7.92 (d, 1H, J=16.2 Hz),... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.CCOc1cc(OC)c(C=O)cc1-c1cccs1>>CCOc1cc(OC)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7aa117440654800b740f7e31e8883ad | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(O)c(-c2cccs2)cc1C=O>>COc1cc(O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | Cl.OC1=CC(=C(C=O)C=C1C=1SC=CC1)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1.C[O-].[Li+]>>OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC | [CH3:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([C:23](=[O:24])[OH:25])[cH:26][cH:27]1.O=[CH:15][c:14]1[c:3]([O:2][CH3:1])[cH:4][c:5]([OH:6])[c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[cH:13][c:14]1/[CH:15]=[CH:16]/[C:17](=[O:18])[... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(O)c(-c2cccs2)cc1C=O | COc1cc(O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | O.CN(C=O)C.CO.C(C)O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 5 | [{"value": 5.0, "product": "OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.1, "product": "OC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 4-Hydroxy-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-47B, 0.30 g, 0.86 mmol) and 4-acetylbenzoic acid (0.13 g, 0.86 mmol) were dissolved in a dimethylformamide-methanol solution (6 mL, 7:3). After complete dissolution, lithium methoxide (0.12 g, 3.3 mmol) was added and the resulting red slurry was stirred in the dark a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | O.CN(C=O)C.CO.C(C)O | null | 18 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(O)c(-c2cccs2)cc1C=O>O.CN(C=O)C.CO.C(C)O>COc1cc(O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e2715e8373664ae8829364fb63a82860 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nccs2)cc1C=O>>COc1cc(OC)c(-c2nccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CN1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C(=C1)OC)C=1SC=CN1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][cH:11][cH:12][s:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][cH:11][cH:12][s:13]2)[cH:14][c:15]1/[CH:16]=[CH:17]/[C:1... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nccs2)cc1C=O | COc1cc(OC)c(-c2nccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2nccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 65 | [{"value": 65.0, "product": "COC1=C(C=C(C(=C1)OC)C=1SC=CN1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-thiazol-2-yl-benzaldehyde (Ex-55A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp>260° C., 65% yield. 1H-NMR (DMSO-d6) δ 13.33 (bs, 1H), 8.74 (s, 1H), 8.22 (d, J=8 Hz, 2H), 8.04–8.12 (m, 3H), 7.95 (d, J=2 Hz, 1H), 7.82 (d... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cscn1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nccs2)cc1C=O>>COc1cc(OC)c(-c2nccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d609123f72e340f8a6b558bc8f9e3250 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cccn2C(=O)OC(C)(C)C)cc1C=O>>COc1cc(OC)c(-c2cccn2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | C(C)(C)(C)OC(=O)N1C(=CC=C1)C1=C(C=C(C(=C1)C=O)OC)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>C(C)(C)(C)OC(=O)N1C(=CC=C1)C1=C(C=C(C(=C1)\C=C\C(=O)C1=CC=C(C=C1)C(=O)O)OC)OC | [CH3:24][C:25](=[O:26])[c:27]1[cH:28][cH:29][c:30]([C:31](=[O:32])[OH:33])[cH:34][cH:35]1.O=[CH:23][c:22]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13]2[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10]... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cccn2C(=O)OC(C)(C)C)cc1C=O | COc1cc(OC)c(-c2cccn2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2ccc[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 6 | [{"value": 6.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC=C1)C1=C(C=C(C(=C1)\\C=C\\C(=O)C1=CC=C(C=C1)C(=O)O)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-(5-formyl-2,4-dimethoxy-phenyl)-pyrrole-1-carboxylic acid tert-butyl ester (Ex-57A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 205–207° C., 6% yield. 1H-NMR (DMSO-d6) δ 8.19 (d, J=5 Hz, 2H), 8.00–8.10 (m, 3H), 7.87 (s, 1H), 7.80 (d... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc[nH]1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cccn2C(=O)OC(C)(C)C)cc1C=O>>COc1cc(OC)c(-c2cccn2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2abe984cff548c283fad39ead5f0743 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(O)c(C=O)cc1-c1cccs1>>COc1cc(O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | Cl.OC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1.C[O-].[Li+]>>OC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20]1.O=[CH:8][c:7]1[c:5]([OH:6])[cH:4][c:3]([O:2][CH3:1])[c:22](-[c:23]2[cH:24][cH:25][cH:26][s:27]2)[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7](/[CH:8]=[CH:9]/[C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(O)c(C=O)cc1-c1cccs1 | COc1cc(O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | O.CN(C=O)C.CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 15.3 | [{"value": 15.0, "product": "OC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "OC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 2-Hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-29B, 0.10 g, 0.43 mmol) and 4-acetylbenzoic acid (0.070 g, 0.43 mmol) were dissolved in a dimethylformamide-methanol solution (2.8 mL, 7:3). After complete dissolution, lithium methoxide (0.065 g, 1.7 mmol) was added and the resulting red slurry was stirred in the da... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | O.CN(C=O)C.CO | null | 18 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(O)c(C=O)cc1-c1cccs1>O.CN(C=O)C.CO>COc1cc(O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd9f6914b354462999ee8b032cab976b | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC(C)(C)C(=O)O)c(C=O)cc1-c1cccs1>>COc1cc(OC(C)(C)C(=O)O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | Cl.C(=O)C1=C(OC(C(=O)O)(C)C)C=C(C(=C1)C=1SC=CC1)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1.C[O-].[Li+]>>C(=O)(O)C(C)(OC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C | [CH3:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1.O=[CH:14][c:13]1[c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:12])[cH:4][c:3]([O:2][CH3:1])[c:28](-[c:29]2[cH:30][cH:31][cH:32][s:33]2)[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:1... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC(C)(C)C(=O)O)c(C=O)cc1-c1cccs1 | COc1cc(OC(C)(C)C(=O)O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | O.CN(C=O)C.CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 85 | [{"value": 85.0, "product": "C(=O)(O)C(C)(OC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "C(=O)(O)C(C)(OC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-(2-Formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-59B, 0.12 g, 0.39 mmol) and 4-acetylbenzoic acid (0.064 g, 0.39 mmol) were dissolved in a dimethylformamide-methanol solution (2.7 mL, 7:3). After complete dissolution, lithium methoxide (0.060 g, 1.6 mmol) was added and the resulting bright ora... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | O.CN(C=O)C.CO | null | 2 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC(C)(C)C(=O)O)c(C=O)cc1-c1cccs1>O.CN(C=O)C.CO>COc1cc(OC(C)(C)C(=O)O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7f81d6e4fb24ae099acd0a0c7aec7fd | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCCN2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | Cl.COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCCN1CCOCC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1.C[O-].[Li+]>>Cl.COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OCCN1CCOCC1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]1.O=[CH:16][c:15]1[c:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:4][c:3]([O:2][CH3:1])[c:30](-[c:31]2[cH:32][cH:33][cH:34][s:35]2)[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCCN2CCOCC2)c(C=O)cc1-c1cccs1 | COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | O.CN(C=O)C.CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCCN1CCOCC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "Cl.COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-benzaldehyde (Ex-60A, 0.15 g, 0.43 mmol) and 4-acetylbenzoic acid (0.071 g, 0.43 mmol) were dissolved in a dimethylformamide-methanol solution (3.0 mL, 7:3). After complete dissolution, lithium methoxide (0.065 g, 1.7 mmol) was added and the resulting bright orange ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccsc1 | HO- | O.CN(C=O)C.CO | null | 2 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCCN2CCOCC2)c(C=O)cc1-c1cccs1>O.CN(C=O)C.CO>COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e936e358d2f4910be2c07fb3e247bb1 | COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O | C(Cl)Cl.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)C=O)OC)OC.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>>N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C=O)C1)OC)OC | CC(C)(C)OC(=O)[n:17]1[c:9](-[c:8]2[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:19]([CH:20]=[O:21])[cH:18]2)[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[nH:17]2)[cH:18][c:19]1[CH:20]=[O:21] | COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O | null | null | C1CCOC1 | Reduction | Boc amine deprotection | eefd4487d640b2607d7a60d065f8822bc457add01d643b9dbf7d76d9b4bfeca6 | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | c1ccc(-c2cc3ccccc3[nH]2)cc1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4]:[c:5]:[c:6]:1-[c:7]>>[c:3]:[c:2]1:[c:4]:[c:5]:[c:6](-[c:7]):[nH;D2;+0:1]:1 | 30.8 | [{"value": 30.0, "product": "N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C=O)C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.8, "product": "N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C=O)C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Ex-61A: 2-(5-Formyl-2,4-dimethoxy-phenyl)-indole-1-carboxylic acid tert-butyl ester (Ex-36A, 2.0 g, 5.2 mmol) was dissolved in 100 ml of THF, and Bu4NF (6.86 g, 26 mmol) was added. The reaction mixture was stirred at room temperature overnight. No reaction occured at this condition. Then, Bu4NF (6.86 g, 26 mmol) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1cc2ccccc2[nH]1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | C1CCOC1 | null | 8 | COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O>C1CCOC1>COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ddfaf0a48a44d8bacdcd8eaf156be91 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C=O)C1)OC)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[nH:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:1... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 66 | [{"value": 66.0, "product": "N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 5-(1H-indol-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-61A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Red solid, mp 210–212° C., 66% yield. 1H-NMR (Aceton-d6) δ 10.53 (br, s, 1H), 8.32 (s, 1H), 8.14–8.21 (m, 5H), 7.89 (d, J=15 Hz, 1H), 7.52 (d, J=8 Hz, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db9d400ae05d48d8a73cef95d7c4ce31 | C1CCNC1.O=Cc1cc(-c2cccs2)ccc1F>>O=Cc1cc(-c2cccs2)ccc1N1CCCC1 | FC1=C(C=O)C=C(C=C1)C=1SC=CC1.N1CCCC1>>N1(CCCC1)C1=C(C=O)C=C(C=C1)C=1SC=CC1 | [NH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1.F[c:13]1[c:3]([CH:2]=[O:1])[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][cH:12]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | C1CCNC1.O=Cc1cc(-c2cccs2)ccc1F | O=Cc1cc(-c2cccs2)ccc1N1CCCC1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1csc(-c2ccc(N3CCCC3)cc2)c1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:6]=[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1):[c:2]:[c:3] | 32 | [{"value": 32.0, "product": "N1(CCCC1)C1=C(C=O)C=C(C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-63A: A solution of 2-fluoro-5-thiophen-2-yl-benzaldehyde (1.42 g, 6.89 mmol) in pyrrolidine was refluxed (10 mL). After 4.5 days the reaction mixture was cooled and diluted with ethyl acetate. The solution of ethyl acetate was washed with hydrochloric acid (0.5M) sodium carbonate (2M) and saturated solution of sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.c1ccsc1.C1CC[NH]C1 | HF | C(C)(=O)OCC | null | null | C1CCNC1.O=Cc1cc(-c2cccs2)ccc1F>C(C)(=O)OCC>O=Cc1cc(-c2cccs2)ccc1N1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7dbd754bf91c4bb18f0bbef2763fd3b3 | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1cc(-c2cccs2)ccc1N1CCCC1>>O=C(O)c1ccc(C(=O)/C=C/c2cc(-c3cccs3)ccc2N2CCCC2)cc1 | N1(CCCC1)C1=C(C=O)C=C(C=C1)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>N1(CCCC1)C1=C(C=C(C=C1)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH3:10])[cH:28][cH:29]1.O=[CH:11][c:12]1[cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][s:19]2)[cH:20][cH:21][c:22]1[N:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])/[CH:10]=[CH:11]/[c:12]2[cH:13][c:14](-[c:15]3[cH:16]... | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1cc(-c2cccs2)ccc1N1CCCC1 | O=C(O)c1ccc(C(=O)/C=C/c2cc(-c3cccs3)ccc2N2CCCC2)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1N1CCCC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 2-pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde (Ex-63A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Red solid, mp 208–209° C. 1H-NMR (DMSO-d6) δ 12.50 (bs, 1H), 8.22 (d, J=8.5 Hz, 2H), 8.09–7.99 (m, 4H), 7.73 (d, J=15.5 Hz, 1H), 7.52–7.41 (m, 3H), 7.1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1.C1CC[NH]C1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1cc(-c2cccs2)ccc1N1CCCC1>>O=C(O)c1ccc(C(=O)/C=C/c2cc(-c3cccs3)ccc2N2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-465275cc1e2146188b98a388bd049399 | CC(C)(C)[SiH2]OC(C)(C)C(CO[Si](C)(C)C(C)(C)C)COS(C)(=O)=O.COc1cc(O)c(C=O)cc1-c1cccs1>>COc1cc(OCC(CO[Si](C)(C)C(C)(C)C)C(C)(C)O[SiH2]C(C)(C)C)c(C=O)cc1-c1cccs1 | C(C)(C)(C)[Si](OCC(COS(=O)(=O)C)C(O[SiH2]C(C)(C)C)(C)C)(C)C.OC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)[Si](OCC(COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1)C(O[SiH2]C(C)(C)C)(C)C)(C)C | CS(=O)(=O)O[CH2:7][CH:8]([CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[C:18]([CH3:19])([CH3:20])[O:21][SiH2:22][C:23]([CH3:24])([CH3:25])[CH3:26].[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:27]([CH:28]=[O:29])[cH:30][c:31]1-[c:32]1[cH:33][cH:34][cH:35][s:36]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:... | CC(C)(C)[SiH2]OC(C)(C)C(CO[Si](C)(C)C(C)(C)C)COS(C)(=O)=O.COc1cc(O)c(C=O)cc1-c1cccs1 | COc1cc(OCC(CO[Si](C)(C)C(C)(C)C)C(C)(C)O[SiH2]C(C)(C)C)c(C=O)cc1-c1cccs1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 57201f1afbda3b7775282ca8e3c59a4fb8e542f888bbdbfa994f08238598f88e | b300ae9ac00448343b04f8595ac10c40ddc175401f75ad1a9cb423839305bb59 | c1ccc(-c2cccs2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C:3]-[C:2](-[C:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:6]=[O;D1;H0:5] | 81 | [{"value": 10.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "C(C)(C)(C)[Si](OCC(COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1)C(O[SiH2]C(C)(C)C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "C(C)(C)(C)[Si](OCC(COC1=C(C=O)C=C(C(=C1)OC)C=1SC=... | 80 | CELSIUS | 24 | HOUR | Ex-64A: To a solution of 2-hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde (10.0 g, 42.7 mmol) in N,N-dimethylformamide (100 mL) was added potassium carbonate (11.8 g, 85.4 mmol) and the resulting yellow slurry was heated to 80° C. Once at 80° C., methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dim... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccsc1 | MsOH.HO- | O.CN(C=O)C | 80 | 24 | CC(C)(C)[SiH2]OC(C)(C)C(CO[Si](C)(C)C(C)(C)C)COS(C)(=O)=O.COc1cc(O)c(C=O)cc1-c1cccs1>O.CN(C=O)C>COc1cc(OCC(CO[Si](C)(C)C(C)(C)C)C(C)(C)O[SiH2]C(C)(C)C)c(C=O)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7cb4efff7e194367b770732e5e161228 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(CO)CO)c(C=O)cc1-c1cccs1>>COc1cc(OCC(CO)CO)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | OCC(COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1)CO.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>OCC(COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)CO | [CH3:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1.O=[CH:14][c:13]1[c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][OH:12])[cH:4][c:3]([O:2][CH3:1])[c:28](-[c:29]2[cH:30][cH:31][cH:32][s:33]2)[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][OH:12]... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(CO)CO)c(C=O)cc1-c1cccs1 | COc1cc(OCC(CO)CO)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 61 | [{"value": 61.0, "product": "OCC(COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-(3-hydroxy-2-hydroxymethyl-propoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-64B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Light orange solid, mp 219–220° C., 61% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.36 (s, 1H), 8.20 (d, 2H, J=7.5 Hz), 8.05–8.1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(CO)CO)c(C=O)cc1-c1cccs1>>COc1cc(OCC(CO)CO)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac9418c514e14ffda68996d6b85f8680 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(=O)N(C)C)c(C=O)cc1-c1cccs1>>COc1cc(OCC(=O)N(C)C)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | C(=O)C1=C(OCC(=O)N(C)C)C=C(C(=C1)C=1SC=CC1)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>CN(C(=O)COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C | [CH3:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1.O=[CH:14][c:13]1[c:5]([O:6][CH2:7][C:8](=[O:9])[N:10]([CH3:11])[CH3:12])[cH:4][c:3]([O:2][CH3:1])[c:28](-[c:29]2[cH:30][cH:31][cH:32][s:33]2)[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][C:8](=[O:9])[N:10]([CH3:11])[CH3:12]... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(=O)N(C)C)c(C=O)cc1-c1cccs1 | COc1cc(OCC(=O)N(C)C)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": "CN(C(=O)COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-N,N-dimethyl-acetamide (Ex-67A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 228–229° C., 75% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.31 (d, 2H, J=9.3 Hz), 8.22 (d, 2H, J=13.3 Hz), 8.08 (d, 2... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(=O)N(C)C)c(C=O)cc1-c1cccs1>>COc1cc(OCC(=O)N(C)C)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dfba431f171450685223b10c4f9e620 | CC(=O)c1ccc(C(=O)O)cc1.COCCOCCOCCOc1cc(OC)c(-c2cccs2)cc1C=O>>COCCOCCOCCOc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCCOCCOCCOC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OCCOCCOCCOC | [CH3:26][C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([C:33](=[O:34])[OH:35])[cH:36][cH:37]1.O=[CH:25][c:24]1[c:12]([O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:13][c:14]([O:15][CH3:16])[c:17](-[c:18]2[cH:19][cH:20][cH:21][s:22]2)[cH:23]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C... | CC(=O)c1ccc(C(=O)O)cc1.COCCOCCOCCOc1cc(OC)c(-c2cccs2)cc1C=O | COCCOCCOCCOc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OCCOCCOCCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-methoxy-2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-5-thiophen-2-yl-benzaldehyde (Ex-68B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 137–138° C., 82% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.20–8.23 (m, 3H), 8.09 (d, 2H, J=8.3 Hz), 8.01... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COCCOCCOCCOc1cc(OC)c(-c2cccs2)cc1C=O>>COCCOCCOCCOc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3354c3f1f1324b749c5386a892babfc9 | CC(N)=S.COc1ccc(C(=O)CBr)cc1OC>>COc1ccc(-c2csc(C)n2)cc1OC | BrCC(=O)C1=CC(=C(C=C1)OC)OC.C(C)(=S)N>>COC=1C=C(C=CC1OC)C=1N=C(SC1)C | [S:9]=[C:10]([CH3:11])[NH2:12].O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:14]([O:15][CH3:16])[cH:13]1)[CH2:8]Br>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][s:9][c:10]([CH3:11])[n:12]2)[cH:13][c:14]1[O:15][CH3:16] | CC(N)=S.COc1ccc(C(=O)CBr)cc1OC | COc1ccc(-c2csc(C)n2)cc1OC | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1ccc(-c2cscn2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11]>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[cH;D2;+0:1]:[s;H0;D2;+0:11]:1 | 100 | [{"value": 100.0, "product": "COC=1C=C(C=CC1OC)C=1N=C(SC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "COC=1C=C(C=CC1OC)C=1N=C(SC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-69A: A solution of 2-bromo-1-(3,4-dimethoxy-phenyl)-ethanone (0.62 g, 2.39 mmol) and thioacetamide (0.18 g, 2.39 mmol) in ethanol (30 mL) was refluxed for 2 hours and the solvent was removed under reduced pressure. The product, 4-(3,4-dimethoxy-phenyl)-2-methyl-thiazole (0.56 g, 100%) was obtained as a white solid a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1ccccc1.c1cscn1 | HBr | C(C)O | null | null | CC(N)=S.COc1ccc(C(=O)CBr)cc1OC>C(C)O>COc1ccc(-c2csc(C)n2)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de02eab211fe46eb88ec524083dacd35 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2csc(C)n2)cc1C=O>>COc1cc(OC)c(-c2csc(C)n2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C=C(C(=C1)OC)C=1N=C(SC1)C.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C(=C1)OC)C=1N=C(SC1)C)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29]1.O=[CH:17][c:16]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][s:11][c:12]([CH3:13])[n:14]2)[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][s:11][c:12]([CH3:13])[n:14]2)[cH:15][c:16]1/[C... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2csc(C)n2)cc1C=O | COc1cc(OC)c(-c2csc(C)n2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cscn2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-(2-methyl-thiazol-4-yl)-benzaldehyde (Ex-69A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 201–202° C. (dec.). 1H-NMR (DMSO-d6) δ 8.47 (s, 1H), 8.14–7.97 (m, 5H), 7.76 (s, 1H), 7.65 (d, J=15.8 Hz, 1H), 6.81 (s, 1H), 4.0... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cscn1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2csc(C)n2)cc1C=O>>COc1cc(OC)c(-c2csc(C)n2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d8916d749ee4c9582da95c822c09a05 | COc1ccc(C=O)c(OC)c1.Nc1ccccc1N>>COc1ccc(-c2nc3ccccc3[nH]2)c(OC)c1 | C=1(C(=CC=CC1)N)N.COC1=C(C=O)C=CC(=C1)OC.C(C)(=O)O>>COC1=C(C=CC(=C1)OC)C1=NC2=C(N1)C=CC=C2 | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][c:16]1[O:17][CH3:18].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH2:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[nH:15]2)[c:16]([O:17][CH3:18])[cH:19]1 | COc1ccc(C=O)c(OC)c1.Nc1ccccc1N | COc1ccc(-c2nc3ccccc3[nH]2)c(OC)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:12]:[c:11](:[c:13]):[c:9](:[c:10]):[nH;D2;+0:8]:1):[c:3]:[c:4] | 12.4 | [{"value": 12.0, "product": "COC1=C(C=CC(=C1)OC)C1=NC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.4, "product": "COC1=C(C=CC(=C1)OC)C1=NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-70A: A solution of benzene-1,2-diamine (2.60 g, 24.1 mmol) and 2,4-dimethoxy-benzaldehyde (4.0 g, 24.1 mmol) in ethanol (60 mL) containing catalytic amount of acetic acid was refluxed overnight. Solvent was then evaporated under reduced pressure. The residue oil was triturated in ethyl acetate to obtain 2-(2,4-dimet... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | C(C)O | null | null | COc1ccc(C=O)c(OC)c1.Nc1ccccc1N>C(C)O>COc1ccc(-c2nc3ccccc3[nH]2)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99c75083b617400881a3414a539d1dc2 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nc3ccccc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2nc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | N1C(=NC2=C1C=CC=C2)C=2C(=CC(=C(C=O)C2)OC)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>N1C(=NC2=C1C=CC=C2)C=2C(=CC(=C(C2)/C=C/C(=O)C2=CC=C(C(=O)O)C=C2)OC)OC | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[nH:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14]... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nc3ccccc3[nH]2)cc1C=O | COc1cc(OC)c(-c2nc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2nc3ccccc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 5-(1H-benzoimidazol-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-70A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp>240° C. (dec.). 1H-NMR (DMSO-d6) δ 8.72 (s, 1H), 12.10 (s, 1H), 8.18 (d, J=8.4 Hz, 2H), 8.08–8.02 (m, 3H), 7.80 (d, J=15.4 Hz, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nc3ccccc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2nc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a19a657cbf0448f4afbd723ca73bee44 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(N)=O)c(C=O)cc1-c1cccs1>>COc1cc(OCC(N)=O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | C(=O)C1=C(OCC(=O)N)C=C(C(=C1)C=1SC=CC1)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>C(N)(=O)COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1.O=[CH:12][c:11]1[c:5]([O:6][CH2:7][C:8]([NH2:9])=[O:10])[cH:4][c:3]([O:2][CH3:1])[c:26](-[c:27]2[cH:28][cH:29][cH:30][s:31]2)[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][C:8]([NH2:9])=[O:10])[c:11](/[CH:12]=[CH:13]/[C:14](... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(N)=O)c(C=O)cc1-c1cccs1 | COc1cc(OCC(N)=O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 70 | [{"value": 70.0, "product": "C(N)(=O)COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-acetamide (Ex-71A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 70% yield, mp 235° C. (dec.). 1H-NMR (300 MHz, DMSO-d6) δ 8.26–8.30 (m, 3H), 8.08–8.11 (m, 4H), 7.67 (d, 1H, J=2.7 Hz), 7.65 (b... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(N)=O)c(C=O)cc1-c1cccs1>>COc1cc(OCC(N)=O)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-897bf0507d314d2c90398876c7853846 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(=O)N2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCC(=O)N2CCOCC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCC(=O)N1CCOCC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OCC(=O)N1CCOCC1 | [CH3:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29]1.O=[CH:17][c:16]1[c:5]([O:6][CH2:7][C:8](=[O:9])[N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[cH:4][c:3]([O:2][CH3:1])[c:31](-[c:32]2[cH:33][cH:34][cH:35][s:36]2)[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][C:8](=[O:9])[N... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(=O)N2CCOCC2)c(C=O)cc1-c1cccs1 | COc1cc(OCC(=O)N2CCOCC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCC(=O)N1CCOCC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 70 | [{"value": 70.0, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OCC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-methoxy-2-(2-morpholin-4-yl-2-oxo-ethoxy)-5-thiophen-2-yl-benzaldehyde (Ex-72A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Orange solid, mp 231–233° C., 70% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.28–8.35 (m, 3H), 8.21 (s, 1H), 8.07–8.11 (m, 3H), 7.66... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC(=O)N2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCC(=O)N2CCOCC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5a59805c40043619e3eed95fb6c9b8a | CC(C)(C)OC(=O)n1cc(B2OC(C)(C)C(C)(C)O2)cn1.COc1cc(OC)c(C=O)cc1Br>>COc1cc(OC)c(-c2cnn(C(=O)OC(C)(C)C)c2)cc1C=O | COC1=C(C=O)C=C(C(=C1)OC)Br.C(C)(C)(C)OC(=O)N1N=CC(=C1)B1OC(C(O1)(C)C)(C)C.[F-].[K+].[F-].[K+]>>C(C)(C)(C)OC(=O)N1N=CC(=C1)C1=C(C=C(C(=C1)C=O)OC)OC | CC1(C)OB([c:9]2[cH:10][n:11][n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]2)OC1(C)C.Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:22]([CH:23]=[O:24])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:... | CC(C)(C)OC(=O)n1cc(B2OC(C)(C)C(C)(C)O2)cn1.COc1cc(OC)c(C=O)cc1Br | COc1cc(OC)c(-c2cnn(C(=O)OC(C)(C)C)c2)cc1C=O | null | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C | O | C-C Coupling | Suzuki coupling with boronic esters | 8486b628dc2367f7863c9ec20cbd73e86fafe30117c96c3513a818c3b3e559a3 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2cn[nH]c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].C-C1(-C)-O-B(-[c;H0;D3;+0:9]2:[c:10]:[#7;a:11]:[#7;a:12](-[C:13](-[#8:14])=[O;D1;H0:15]):[c:16]:2)-O-C-1(-C)-C>>[#8:14]-[C:13](=[O;D1;H0:15])-[#7;a:12]1:[#7;a:11]:[c:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[... | 40 | [{"value": 40.0, "product": "C(C)(C)(C)OC(=O)N1N=CC(=C1)C1=C(C=C(C(=C1)C=O)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.9, "product": "C(C)(C)(C)OC(=O)N1N=CC(=C1)C1=C(C=C(C(=C1)C=O)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | Ex-74B: To a mixture of 2,4-dimethoxy-5-bromo-benzaldehye (0.28 g, 1.13 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (Ex-76A, 0.61 g, 1.70 mmol), bis(tri-tert-butylphosphine)palladium (43 mg, 0.085 mmol) and potassium fluoride (0.24 g, 4.08 mmol) was added degassed... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1cn[nH]c1.c1ccccc1 | c1ccccc1.c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1 | HBr.B | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O | 60 | 8 | CC(C)(C)OC(=O)n1cc(B2OC(C)(C)C(C)(C)O2)cn1.COc1cc(OC)c(C=O)cc1Br>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.O>COc1cc(OC)c(-c2cnn(C(=O)OC(C)(C)C)c2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1fce6fa86b44b33a213046a373ec11e | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cn[nH]c2)cc1C=O>>COc1cc(OC)c(-c2cn[nH]c2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C=C(C(=C1)OC)C=1C=NNC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C(=C1)OC)C=1C=NNC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][nH:12][cH:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][nH:12][cH:13]2)[cH:14][c:15]1/[CH:16]=[CH:17]/[C... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cn[nH]c2)cc1C=O | COc1cc(OC)c(-c2cn[nH]c2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cn[nH]c2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-(1H-pyrazol-4-yl)-benzaldehyde (Ex-74B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3 including an acid work-up. Yellow solid, mp>250° C. 1H-NMR (DMSO-d6) δ 12.42 (bs, 1H), 8.20–8.03 (m, 8H), 7.85 (d, J=16.1 Hz), 6.74 (s, 1H), 3.95 (s, 3H... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cn[nH]c1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cn[nH]c2)cc1C=O>>COc1cc(OC)c(-c2cn[nH]c2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a106097291b4be188bdf9f422a00973 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nn[nH]n2)cc1C=O>>COc1cc(OC)c(-c2nn[nH]n2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C=C(C(=C1)OC)C=1N=NNN1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C(=C1)OC)C=1N=NNN1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][nH:12][n:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][nH:12][n:13]2)[cH:14][c:15]1/[CH:16]=[CH:17]/[C:18]... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nn[nH]n2)cc1C=O | COc1cc(OC)c(-c2nn[nH]n2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | CC#N | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2nn[nH]n2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 19 | [{"value": 19.0, "product": "COC1=C(C=C(C(=C1)OC)C=1N=NNN1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-(2H-tetrazol-5-yl)-benzaldehyde (Ex-75A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 19% yield, mp 218° C. (dec). 1H-NMR (DMSO-d6) δ 8.58 (s, 1H), 8.20 (d, 2H), 8.03 (m, 3H), 7.85 (d, 1H), 6.90 (s, 1H), 4.04 (s, 3H), 4.02... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1nnn[nH]1.c1ccccc1 | HO- | CC#N | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nn[nH]n2)cc1C=O>CC#N>COc1cc(OC)c(-c2nn[nH]n2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbaef0eb224e46eaa4d22a25a6a8cb28 | COc1ccc(C(=O)O)c(OC)c1.Nc1cccnc1N>>COc1ccc(-c2nc3cccnc3[nH]2)c(OC)c1 | COC1=C(C(=O)O)C=CC(=C1)OC.O=P(Cl)(Cl)Cl.NC1=NC=CC=C1N>>COC1=C(C=CC(=C1)OC)C1=NC=2C(=NC=CC2)N1 | O=[C:7](O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][c:16]1[O:17][CH3:18].[NH2:8][c:9]1[cH:10][cH:11][cH:12][n:13][c:14]1[NH2:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][n:13][c:14]3[nH:15]2)[c:16]([O:17][CH3:18])[cH:19]1 | COc1ccc(C(=O)O)c(OC)c1.Nc1cccnc1N | COc1ccc(-c2nc3cccnc3[nH]2)c(OC)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 732e0ce9e0b11ff0dfc685a4702602ca2b8a50d1240d37c421f2ec2dce5e88c1 | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc(-c2nc3cccnc3[nH]2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12](:[c:14]):[c:9](:[#7;a:10]:[c:11]):[nH;D2;+0:8]:1):[c:3]:[c:4] | 88 | [{"value": 88.0, "product": "COC1=C(C=CC(=C1)OC)C1=NC=2C(=NC=CC2)N1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.2, "product": "COC1=C(C=CC(=C1)OC)C1=NC=2C(=NC=CC2)N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-76A: To a suspension of 2,4-dimethoxybenzoic acid (0.36 g, 2 mmol) and 8 ml of POCl3 in a 50 ml of a round-bottom flask, 2,3-diaminopyridine (0.22 g, 2 mmol) was added. The mixture was heated to reflux for 4 hours and then cooled to room temperature. The reaction mixture was then concentrated to remove most of the P... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccncc1 | c1cnc2nc[nH]c2c1 | c1ccccc1.c1cnc2nc[nH]c2c1 | HO- | null | null | null | COc1ccc(C(=O)O)c(OC)c1.Nc1cccnc1N>>COc1ccc(-c2nc3cccnc3[nH]2)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b012cffa1faa47589059e872491db161 | COc1ccc(-c2nc3cccnc3[nH]2)c(OC)c1>>COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O | COC1=C(C=CC(=C1)OC)C1=NC=2C(=NC=CC2)N1.COC(Cl)Cl>>N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C=O)C2)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][n:15][c:16]3[nH:17]2)[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][n:15][c:16]3[nH:17]2)[cH:18][c:19]1[CH:20]=[O:21] | COc1ccc(-c2nc3cccnc3[nH]2)c(OC)c1 | COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O | null | Cl[Ti](Cl)(Cl)Cl | C(Cl)Cl | Miscellaneous | OtherReaction | c25c41cbe22c67cd8a516e3f8fc0980bea758f12933876480aae20d5765822e2 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccc(-c2nc3cccnc3[nH]2)cc1 | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C:7]=[O;D1;H0:8]):[c:5]:[c:6] | 64.4 | [{"value": 63.0, "product": "N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C=O)C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.4, "product": "N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C=O)C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | Ex-76B: To a suspension of 2-(2,4-dimethoxy-phenyl)-3H-imidazo[4,5-b]pyridine (0.44 g, 1.7 mmol) in 20 ml of CH2Cl2, 1,1-dichlorodimethyl ether (0.55 g, 4.8 mmol) was added. The mixture was cooled to 0° C. with a water-ice bath, and 7 ml (7 mmol) of TiCl4 (1.0 m in CH2Cl2) was added dropwise. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnc2nc[nH]c2c1 | Other | Cl[Ti](Cl)(Cl)Cl.C(Cl)Cl | 0 | 2 | COc1ccc(-c2nc3cccnc3[nH]2)c(OC)c1>Cl[Ti](Cl)(Cl)Cl.C(Cl)Cl>COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d74efb6431442d1af68fd61062acc4e | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C=O)C2)OC)OC.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C2)/C=C/C(=O)C2=CC=C(C(=O)O)C=C2)OC)OC | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][n:15][c:16]3[nH:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O | COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2nc3cccnc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 60 | [{"value": 60.0, "product": "N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C2)/C=C/C(=O)C2=CC=C(C(=O)O)C=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 5-(3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-76B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 222–224° C., 60% yield. 1H-NMR (DMSO-d6) δ 8.75 (s, 1H), 8.38–8.40 (m, 1H), 8.18 (d, J=9 Hz, 2H), 7.99–8.08 (m, 4H), 7.8... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cnc2nc[nH]c2c1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c553383d655040c5aa6f9fdb97a2ab62 | CC(=O)Cl.CCOC(=O)C(C)(C)c1ccccc1>>CCOC(=O)C(C)(C)c1ccc(C(C)=O)cc1 | S(O)(O)(=O)=O.C(C)(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-].C(C)OC(C(C)(C1=CC=CC=C1)C)=O>>C(C)OC(C(C)(C)C1=CC=C(C=C1)C(C)=O)=O | Cl[C:13]([CH3:14])=[O:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12]([C:13]([CH3:14])=[O:15])[cH:16][cH:17]1 | CC(=O)Cl.CCOC(=O)C(C)(C)c1ccccc1 | CCOC(=O)C(C)(C)c1ccc(C(C)=O)cc1 | null | null | C(=S)=S | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | 47 | [{"value": 47.0, "product": "C(C)OC(C(C)(C)C1=CC=C(C=C1)C(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.8, "product": "C(C)OC(C(C)(C)C1=CC=C(C=C1)C(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-77A: To a mixture of aluminum chloride (2.8 g, 20.8 mmol) in carbon disulfide (50 mL) was added acetyl chloride (0.74 mL, 10.4 mmol) followed by addition of 2-methyl-2-phenyl-propionic acid ethyl ester (1.0 g, 5.2 mmol). The reaction mixture was refluxed for 2 hours and then poured into ice containing sulfuric acid ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(=S)=S | null | null | CC(=O)Cl.CCOC(=O)C(C)(C)c1ccccc1>C(=S)=S>CCOC(=O)C(C)(C)c1ccc(C(C)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92e59941288a4438a8b274609f6ec176 | CC(=O)c1ccc(C(C)(C)C(=O)O)cc1.COc1cc(OC)c(-c2cccs2)cc1C=O>>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(C)(C)C(=O)O)cc1 | C(C)(=O)C1=CC=C(C=C1)C(C(=O)O)(C)C.COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1>>COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)C(C(=O)O)(C)C | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24]([CH3:25])([CH3:26])[C:27](=[O:28])[OH:29])[cH:30][cH:31]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14]... | CC(=O)c1ccc(C(C)(C)C(=O)O)cc1.COc1cc(OC)c(-c2cccs2)cc1C=O | COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(C)(C)C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 2-(4-acetyl-phenyl)-2-methyl-propionic acid (Ex-77A) and 2,4-dimethoxy-5-thiophen-2-yl-benzaldehyde (Ex-6A) in a similar manner as described in Ex-3. White foam. 1H-NMR (CCDl3) δ 8.11–7.86 (m, 5H), 7.62–7.46 (m, 3H), 7.42 (d, J=3.2 Hz, 1H), 7.31 (d, J=5.3, 1H), 7.10–7.08 (m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(C)(C)C(=O)O)cc1.COc1cc(OC)c(-c2cccs2)cc1C=O>>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(C)(C)C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-228157ee07eb44e19dc9905a42bbafbc | CC(=O)c1ccc(C#N)cc1.[N-]=[N+]=[N-]>>CC(=O)c1ccc(-c2nn[nH]n2)cc1 | C(C)(=O)C1=CC=C(C#N)C=C1.[N-]=[N+]=[N-].[Na+].Cl.CCOC(=O)C>>N=1NN=NC1C1=CC=C(C=C1)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:13][cH:14]1.[N+:10](=[N-:11])=[N-:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][n:10][nH:11][n:12]2)[cH:13][cH:14]1 | CC(=O)c1ccc(C#N)cc1.[N-]=[N+]=[N-] | CC(=O)c1ccc(-c2nn[nH]n2)cc1 | null | [Br-].[Zn+2].[Br-] | O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(-c2nn[nH]n2)cc1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[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;+0:5]1:[n;H0;D2;+0:3]:[nH;D2;+0:1]:[n;H0;D2;+0:2]:[n;H0;D2;+0:4]:1):[c:9]:[c:10] | null | [] | null | null | null | null | Ex-78A: A suspension of 4-acetylbenznitrile (2.9 g, 20.0 mmol), sodium azide (1.43 g, 22.0 mmol) and zinc bromide (4.5 g, 20.0 mmol) in water (50 mL) was refluxed for one day. Additional water (40 mL), HCl (3M, 30 mL) and EtOAc (200 mL) were added subsequently. The mixture was stirred until no solid in the aqueous laye... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | null | [Br-].[Zn+2].[Br-].O | null | null | CC(=O)c1ccc(C#N)cc1.[N-]=[N+]=[N-]>[Br-].[Zn+2].[Br-].O>CC(=O)c1ccc(-c2nn[nH]n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7bb9974605374b57b9e2ab1dd322ffed | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C\C(=O)c1ccc(C(=O)O)cc1 | S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2>>S1C2=C(C=C1C=1C(=CC(=C(C1)\C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2 | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18][c:19]1/[CH:20]=[CH:21]/[C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][c... | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C\C(=O)c1ccc(C(=O)O)cc1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(/C=C\c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | null | 21.7 | [{"value": 21.7, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)\\C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[3E-(5-benzo[b]thien-2-yl-2,4-dimethoxyphenyl)-acryloyl]-benzoic acid (Ex-3, 101.4 mg, 0.23 mmol) in ethyl acetate (889 ml) was stirred in a well lighted-area at room temperature for 36 hours. The solution was concentrated to a yellow solid. The crude material was purified on reversed-phase preparative ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | null | C(C)(=O)OCC | null | null | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1>C(C)(=O)OCC>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C\C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e307b28fe0b34d59bb0d8a3d4186d652 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(C=O)cc1-c1cccs1>>COc1cc(OC(C)(C)C(=O)O)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.C(=O)C1=C(OC(C(=O)O)(C)C)C=C(C(=C1)C=1SC=CC1)OC>>COC=1C(=CC(=C(OC(C(=O)O)(C)C)C1)\C=C\C(C1=CC=C(C=C1)S(=O)(=O)N)=O)C=1SC=CC1 | [CH3:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([S:22]([NH2:23])(=[O:24])=[O:25])[cH:26][cH:27]1.O=[CH:14][c:13]1[c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:12])[cH:4][c:3]([O:2][CH3:1])[c:29](-[c:30]2[cH:31][cH:32][cH:33][s:34]2)[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(C=O)cc1-c1cccs1 | COc1cc(OC(C)(C)C(=O)O)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 85 | [{"value": 85.0, "product": "COC=1C(=CC(=C(OC(C(=O)O)(C)C)C1)\\C=C\\C(C1=CC=C(C=C1)S(=O)(=O)N)=O)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-59B) in a similar manner as described in Ex-22. Yellow solid, mp 164–165° C., 85% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.21–8.28 (m, 3H), 7.96–8.12 (m, 4H), 7.6... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(C=O)cc1-c1cccs1>>COc1cc(OC(C)(C)C(=O)O)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d7a874c547f4e10bf5fff9813a4f7a7 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)C=O)OC)OC>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)\C=C\C(C1=CC=C(C=C1)S(=O)(=O)N)=O)OC)OC | [CH3:28][C:29](=[O:30])[c:31]1[cH:32][cH:33][c:34]([S:35]([NH2:36])(=[O:37])=[O:38])[cH:39][cH:40]1.O=[CH:27][c:26]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 40 | [{"value": 40.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC=C12)C1=C(C=C(C(=C1)\\C=C\\C(C1=CC=C(C=C1)S(=O)(=O)N)=O)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 2-(5-formyl-2,4-dimethoxy-phenyl)-indole-1-carboxylic acid tert-butyl ester (Ex-36A) in a similar manner as described in Ex-22. Yellow solid, 40% yield, mp 120–122° C. 1H-NMR (CDCl3) δ 8.01–8.19 (m, 6H), 7.68 (s, 1H), 7.56 (d, J=8 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cc2ccccc2[nH]1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b7afba2aacb43fd9ab8004bc2469531 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C=O)C1)OC)OC>>N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)OC | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([S:28]([NH2:29])(=[O:30])=[O:31])[cH:32][cH:33]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[nH:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][c... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 70 | [{"value": 70.0, "product": "N1C(=CC2=CC=CC=C12)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 5-(1H-indol-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-61A) in a similar manner as described in Ex-22. Red solid, 70% yield, mp 185–187° C. 1H-NMR (DMSO-d6) δ 11.15 (br, s, 1H), 8.33 (s, 1H), 8.24 (d, J=8 Hz, 2H), 8.07 (d, J=15 Hz, 1H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3[nH]2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-178f6ebd329648339b15e43e2c88429b | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCCCN2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCCCN2CCOCC2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCCCN1CCOCC1>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCCCN1CCOCC1 | [CH3:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([S:25]([NH2:26])(=[O:27])=[O:28])[cH:29][cH:30]1.O=[CH:17][c:16]1[c:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[cH:4][c:3]([O:2][CH3:1])[c:32](-[c:33]2[cH:34][cH:35][cH:36][s:37]2)[cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH2... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCCCN2CCOCC2)c(C=O)cc1-c1cccs1 | COc1cc(OCCCN2CCOCC2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCCCN1CCOCC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 48 | [{"value": 48.0, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 4-methoxy-2-(3-morpholin-4-yl-propoxy)-5-thiophen-2-yl-benzaldehyde (Ex-66A) in a similar manner as described in Ex-22. Yellow solid, 48% yield, mp 193–196° C. 1H-NMR (DMSO-d6) δ 8.24 (m, 3H), 8.06 (s, 1H), 7.96 (d, 2H), 7.89 (d, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCCCN2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCCCN2CCOCC2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5d0065b0beb4a9089063d96da5c0eb4 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCC(CO)CO)c(C=O)cc1-c1cccs1>>COc1cc(OCC(CO)CO)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | OCC(COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1)CO.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.C[O-].[Li+]>>OCC(COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)CO | [CH3:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([S:22]([NH2:23])(=[O:24])=[O:25])[cH:26][cH:27]1.O=[CH:14][c:13]1[c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][OH:12])[cH:4][c:3]([O:2][CH3:1])[c:29](-[c:30]2[cH:31][cH:32][cH:33][s:34]2)[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCC(CO)CO)c(C=O)cc1-c1cccs1 | COc1cc(OCC(CO)CO)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | O.CN(C=O)C.CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 60 | [{"value": 60.0, "product": "OCC(COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.0, "product": "OCC(COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2-(3-Hydroxy-2-hydroxymethyl-propoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-64B) (8.0 g, 24.8 mmol) and 4-acetylbenzenesulfonamide (4.9 g, 24.8 mmol) were dissolved in a dimethylformamide-methanol solution (170 mL, 7:3). After complete dissolution, lithium methoxide (3.8 g, 99.2 mmol) was added and the resulting r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | O.CN(C=O)C.CO | null | 3 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCC(CO)CO)c(C=O)cc1-c1cccs1>O.CN(C=O)C.CO>COc1cc(OCC(CO)CO)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b854c4cccb7741fb8036de2735ec3c46 | COc1cc(OCCN2CCOCC2)c(C=CC(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1>>COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | COC1=CC(=C(C=C1C=1SC=CC1)C=CC(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCCN1CCOCC1.Cl>>Cl.COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCCN1CCOCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[c:15]([CH:16]=[CH:17][C:18](=[O:19])[c:20]2[cH:21][cH:22][c:23]([S:24]([NH2:25])(=[O:26])=[O:27])[cH:28][cH:29]2)[cH:30][c:31]1-[c:32]1[cH:33][cH:34][cH:35][s:36]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH2:8][N:9]2[CH2... | COc1cc(OCCN2CCOCC2)c(C=CC(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(/C=C/c1cc(-c2cccs2)ccc1OCCN1CCOCC1)c1ccccc1 | null | 78 | [{"value": 78.0, "product": "Cl.COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Th 4-{3-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzenesulfonamide (Ex-81, 0.065 g, 0.12 mmol) was dissolved in tetrahydrofuran (5 mL) and 3 N HCl (1 mL) was added drop wise to the solution. The resulting yellow slurry was stirred in the dark at room temperature for 30 min. The precipit... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccsc1 | null | O1CCCC1 | null | 0.5 | COc1cc(OCCN2CCOCC2)c(C=CC(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1>O1CCCC1>COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe789f3e21504dca864cbca9d901392b | COc1cc(OCC#N)c(C(C)=O)cc1-c1cccs1.[N-]=[N+]=[N-]>>COc1cc(OCc2nnn[nH]2)c(C=O)cc1-c1cccs1 | [N-]=[N+]=[N-].[Na+].Cl.C(C)(C)O.C(C)(C)O.C(C)(=O)C1=C(OCC#N)C=C(C(=C1)C=1SC=CC1)OC>>COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCC1=NN=NN1 | C[C:14]([c:13]1[c:5]([O:6][CH2:7][C:8]#[N:9])[cH:4][c:3]([O:2][CH3:1])[c:17](-[c:18]2[cH:19][cH:20][cH:21][s:22]2)[cH:16]1)=[O:15].[N+:10](=[N-:11])=[N-:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[n:9][n:10][n:11][nH:12]2)[c:13]([CH:14]=[O:15])[cH:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21][s:22]1 | COc1cc(OCC#N)c(C(C)=O)cc1-c1cccs1.[N-]=[N+]=[N-] | COc1cc(OCc2nnn[nH]2)c(C=O)cc1-c1cccs1 | null | [Br-].[Zn+2].[Br-] | O.C(C)(=O)OCC.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 354199da06c9f4aea449a83fd668514a7e3c3e4c7259617cc7c2b6c8d5d9f6b3 | 57ff3a51db4f26620c21d3d407c28c01f7f663971bf68682b1481f3486d37946 | c1csc(-c2ccc(OCc3nnn[nH]3)cc2)c1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#8:6]-[C:7]-[C;H0;D2;+0:8]#[N;H0;D1;+0:9].[N-;H0;D1:10]=[N+;H0;D2:11]=[N-;H0;D1:12]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[c:5]-[#8:6]-[C:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[n;H0;D2;+0:11]:[n;H0;D2;+0:10]:[nH;D2;+0:12]:1 | 65 | [{"value": 65.0, "product": "COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCC1=NN=NN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCC1=NN=NN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Ex-89B: (2-Acetyl-5-methoxy-4-thiophen-2-yl-phenoxy)-acetonitrile (Ex-89A, 0.30 g, 1.1 mmol) was slurried in a mixture of water:isopropanol (3 mL, 2:1) to obtain a well-dispersed solution. Sodium azide (0.079 g, 1.2 mmol) followed by zinc bromide (0.25 g, 1.1 mmol) were added and the reaction was heated to reflux and v... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile | Aldehyde | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1.c1ccsc1 | Other | [Br-].[Zn+2].[Br-].O.C(C)(=O)OCC.O1CCCC1 | null | 24 | COc1cc(OCC#N)c(C(C)=O)cc1-c1cccs1.[N-]=[N+]=[N-]>[Br-].[Zn+2].[Br-].O.C(C)(=O)OCC.O1CCCC1>COc1cc(OCc2nnn[nH]2)c(C=O)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fd8cc18eef045a9bc2899c48626f66d | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2nnn[nH]2)c(C=O)cc1-c1cccs1>>COc1cc(OCc2nnn[nH]2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCC1=NN=NN1>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCC1=NN=NN1 | [CH3:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([S:22]([NH2:23])(=[O:24])=[O:25])[cH:26][cH:27]1.O=[CH:14][c:13]1[c:5]([O:6][CH2:7][c:8]2[n:9][n:10][n:11][nH:12]2)[cH:4][c:3]([O:2][CH3:1])[c:29](-[c:30]2[cH:31][cH:32][cH:33][s:34]2)[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[n:9][n:10][n:11][nH:12]2)[... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2nnn[nH]2)c(C=O)cc1-c1cccs1 | COc1cc(OCc2nnn[nH]2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCc1nnn[nH]1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 60 | [{"value": 60.0, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCC1=NN=NN1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 4-methoxy-2-(1H-tetrazol-5-ylmethoxy)-5-thiophen-2-yl-benzaldehyde (Ex-89A) in a similar manner as described in Ex-22. Yellow solid, mp 163–164° C. (dec), 60% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.31–8.34 (m, 3H), 7.92–8.15 (m, 4H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2nnn[nH]2)c(C=O)cc1-c1cccs1>>COc1cc(OCc2nnn[nH]2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42c3b7a2964342848424c8b88130fb7e | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1.NCCN1CCOCC1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)NCCN2CCOCC2)cc1 | S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2.N1(CCOCC1)CCN.Cl.CN(CCCN=C=NCC)C>>S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)NCCN3CCOCC3)C=C1)OC)OC)C=CC=C2 | O[C:28]([c:27]1[cH:26][cH:25][c:24]([C:22](/[CH:21]=[CH:20]/[c:19]2[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]3[cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[s:17]3)[cH:18]2)=[O:23])[cH:40][cH:39]1)=[O:29].[NH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][O:36][CH2:37][CH2:38]1>>[CH3:1][O:2][c:3]1[cH:4][c... | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1.NCCN1CCOCC1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)NCCN2CCOCC2)cc1 | null | null | ClCCl.[Cl-].[Na+].O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccc(C(=O)NCCN2CCOCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 77 | [{"value": 77.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)NCCN3CCOCC3)C=C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 4-[3E-(5-Benzo[b]thien-2-yl-2,4-dimethoxyphenyl)-acryloyl]-benzoic acid (Ex-3, 0.44 mg, 1 mmol) and 2-morpholin-4-yl-ethylamine (0.18 mL) in dichloromethane (20 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.38 g, 2 mmol) and the mixture was stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1.C1COCC[NH]1 | HO- | ClCCl.[Cl-].[Na+].O | null | 4 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1.NCCN1CCOCC1>ClCCl.[Cl-].[Na+].O>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)NCCN2CCOCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06f80710ee084514bbedbcbd6a4d584a | CC(=O)c1ccc(C(=O)O)cc1.N>>CC(=O)c1ccc(C(N)=O)cc1 | N.C(C)(=O)C1=CC=C(C(=O)O)C=C1.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)(=O)C1=CC=C(C(=O)N)C=C1 | O[C:8]([c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:12][cH:11]1)=[O:10].[NH3:9]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([NH2:9])=[O:10])[cH:11][cH:12]1 | CC(=O)c1ccc(C(=O)O)cc1.N | CC(=O)c1ccc(C(N)=O)cc1 | null | null | O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 50.2 | [{"value": 50.0, "product": "C(C)(=O)C1=CC=C(C(=O)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "C(C)(=O)C1=CC=C(C(=O)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Ex-92A: To a solution of 4-acetyl-benzoic acid (0.5 g, 3.05 mmol) in tetrahydrofuran (10 mL) was added carbonyldiimidazole (0.74 g, 4.75 mmol). The solution was allowed to stir at ambient temperature for one hour and cooled to 0° C. followed by addition of ammonia (28% in water, 3 mL, 21 mmol). The solution was continu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 1 | CC(=O)c1ccc(C(=O)O)cc1.N>O1CCCC1>CC(=O)c1ccc(C(N)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65a52f3bb4944230af47e3a45db65550 | CC(=O)c1ccc(C(N)=O)cc1.COc1cc(OCCN2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(N)=O)cc2)cc1-c1cccs1 | C(C)(=O)C1=CC=C(C(=O)N)C=C1.N1(CCOCC1)CCOC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C[O-].[Li+]>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OCCN1CCOCC1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24]([NH2:25])=[O:26])[cH:27][cH:28]1.O=[CH:16][c:15]1[c:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:4][c:3]([O:2][CH3:1])[c:30](-[c:31]2[cH:32][cH:33][cH:34][s:35]2)[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10]... | CC(=O)c1ccc(C(N)=O)cc1.COc1cc(OCCN2CCOCC2)c(C=O)cc1-c1cccs1 | COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(N)=O)cc2)cc1-c1cccs1 | null | null | CO.CN(C)C=O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCCN1CCOCC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 57.1 | [{"value": 57.0, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.1, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-acetyl-benzamide (Ex-92A, 0.25 g, 1.53 mmol) and 2-(2-morpholin-4-yl-ethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-60A, 0.53 g, 1.53 mmol) in DMF (7 mL) and methanol (3 mL) was added lithium methoxide. The solution was allowed to stir at ambient temperature. The reaction was quenched with water ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccsc1 | HO- | CO.CN(C)C=O | null | null | CC(=O)c1ccc(C(N)=O)cc1.COc1cc(OCCN2CCOCC2)c(C=O)cc1-c1cccs1>CO.CN(C)C=O>COc1cc(OCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(N)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83f26efa6ff243ebbe947609441c9c26 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1.[NH4+]>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(N)=O)cc1 | S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2.Cl.CN(CCCN=C=NCC)C.O.ON1N=NC2=C1C=CC=C2.[Cl-].[NH4+].C(C)N(CC)CC>>S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OC)OC)C=CC=C2 | O[C:28]([c:27]1[cH:26][cH:25][c:24]([C:22](/[CH:21]=[CH:20]/[c:19]2[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]3[cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[s:17]3)[cH:18]2)=[O:23])[cH:32][cH:31]1)=[O:30].[NH4+:29]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH... | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1.[NH4+] | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(N)=O)cc1 | null | null | CN(C=O)C | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH4+;D0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 94.2 | [{"value": 94.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OC)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-acetyl-benzamide (0.3 g, 1.84 mmol) and 5-(benzo[b]thein-2yl)-2,4-dimethoxybenzaldehyde (0.55 g, 1.84 mmol) in a mixture of N,N-dimethylformamide (7 mL) and methanol (3 mL) was added lithium methoxide (0.14 g, 3.68 mmol). The reaction mixture was allowed to stir at ambient temperature for 9 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | HO- | CN(C=O)C | null | 8 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1.[NH4+]>CN(C=O)C>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(N)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b049e5eded0421d881d0525f5536767 | CC(=O)c1ccc(C(N)=O)cc1.COc1cc(OCCCN2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(N)=O)cc2)cc1-c1cccs1 | C(C)(=O)C1=CC=C(C(=O)N)C=C1.COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCCCN1CCOCC1>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OCCCN1CCOCC1 | [CH3:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([C:25]([NH2:26])=[O:27])[cH:28][cH:29]1.O=[CH:17][c:16]1[c:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[cH:4][c:3]([O:2][CH3:1])[c:31](-[c:32]2[cH:33][cH:34][cH:35][s:36]2)[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9... | CC(=O)c1ccc(C(N)=O)cc1.COc1cc(OCCCN2CCOCC2)c(C=O)cc1-c1cccs1 | COc1cc(OCCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(N)=O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCCCN1CCOCC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 4-Acetyl-benzamide (Ex-92A) and 4-methoxy-2-(3-morpholin-4-yl-propoxy)-5-thiophen-2-yl-benzaldehyde (Ex-66A) in a similar manner as described in Ex-92. Orange solid, mp 81–83° C. 1H-NMR (CDCl3) δ 8.08 (m, 3H), 7.94 (d, 2H), 7.86 (s, 1H), 7.56 (d, 1H), 7.41 (d, 1H), 7.32 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(N)=O)cc1.COc1cc(OCCCN2CCOCC2)c(C=O)cc1-c1cccs1>>COc1cc(OCCCN2CCOCC2)c(/C=C/C(=O)c2ccc(C(N)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17d25439f80f4b40abf3890546c5bd33 | CC(=O)OC(C)=O.COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(N)=O)cc1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)NC(C)=O)cc1 | S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)N)C=C1)OC)OC)C=CC=C2.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C(C)(=O)OC(C)=O>>C(C)(=O)NC(C1=CC=C(C=C1)C(\C=C\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O | CC(=O)O[C:31]([CH3:32])=[O:33].[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18][c:19]1/[CH:20]=[CH:21]/[C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[NH2:30])[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:1... | CC(=O)OC(C)=O.COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(N)=O)cc1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)NC(C)=O)cc1 | null | null | C1CCOC1 | Acylation | Aminolysis of esters | f8e1e7b3720eef273228103cf264d703ed8d96831ff23382cd877b7383d4fe8d | db323b2eeb801a1f901072d7c90a5131b1469ba68e15c1b73373c24cb0b1f0e2 | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7] | 29.2 | [{"value": 29.0, "product": "C(C)(=O)NC(C1=CC=C(C=C1)C(\\C=C\\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.2, "product": "C(C)(=O)NC(C1=CC=C(C=C1)C(\\C=C\\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | -78 | CELSIUS | 1 | HOUR | A suspension of 4-[3E-(5-benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzamide (Ex-93, 0.5 g, 1.13 mmol) in THF (15 mL) was cooled to −78° C. followed by addition of lithium bis(trimethylsilyl)amide (1.0 M in THF, 2.3 mL, 2.3 mmol). The mixture was stirred at this temperature for 1 hour and warmed up to 0° C.... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amide | Unsubstituted dicarboximide | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | HO- | C1CCOC1 | -78 | 1 | CC(=O)OC(C)=O.COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(N)=O)cc1>C1CCOC1>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)NC(C)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d20f8e28d4694cbc89f6276a2d3db565 | CI.COc1cc(/C=C/C(=O)c2ccc(NS(C)(=O)=O)cc2)cc(-c2cccs2)c1OC>>COc1cc(/C=C/C(=O)c2ccc(N(C)S(C)(=O)=O)cc2)cc(-c2cccs2)c1OC | CI.COC=1C=C(C=C(C1OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)NS(=O)(=O)C.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C(C=C(C1OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)N(S(=O)(=O)C)C | I[CH3:15].[CH3:1][O:2][c:3]1[cH:4][c:5](/[CH:6]=[CH:7]/[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([NH:14][S:16]([CH3:17])(=[O:18])=[O:19])[cH:20][cH:21]2)[cH:22][c:23](-[c:24]2[cH:25][cH:26][cH:27][s:28]2)[c:29]1[O:30][CH3:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[CH:6]=[CH:7]/[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N:14]([... | CI.COc1cc(/C=C/C(=O)c2ccc(NS(C)(=O)=O)cc2)cc(-c2cccs2)c1OC | COc1cc(/C=C/C(=O)c2ccc(N(C)S(C)(=O)=O)cc2)cc(-c2cccs2)c1OC | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[c:7](:[c:8]):[c:9] | 45.9 | [{"value": 45.0, "product": "COC=1C=C(C=C(C1OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)N(S(=O)(=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.9, "product": "COC=1C=C(C=C(C1OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)N(S(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-{4-[3E-(3,4-dimethoxy-5-thiophen-2-yl-phenyl)-acryloyl]-phenyl}-methanesulfonamide (Ex-14, 90 mg, 0.20 mmol) in anhydrous DMF was treated with potassium carbonate (56.1 mg, 0.41). Methyl iodide (126.32 uL, 2.03 mmol) was added to the reaction mixture which was then refluxed for 1.5 hours under inert con... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HI | O.CN(C)C=O | null | null | CI.COc1cc(/C=C/C(=O)c2ccc(NS(C)(=O)=O)cc2)cc(-c2cccs2)c1OC>O.CN(C)C=O>COc1cc(/C=C/C(=O)c2ccc(N(C)S(C)(=O)=O)cc2)cc(-c2cccs2)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e657d09667144e7a75208f9bb28d3d5 | CC(=O)c1ccc(N)cc1.CS(=O)(=O)Cl>>CC(=O)c1ccc(NS(C)(=O)=O)cc1 | CC(=O)C1=CC=C(C=C1)N.N1=CC=CC=C1.S(=O)(=O)(C)Cl>>C(C)(=O)C1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:13][cH:14]1.Cl[S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][S:9]([CH3:10])(=[O:11])=[O:12])[cH:13][cH:14]1 | CC(=O)c1ccc(N)cc1.CS(=O)(=O)Cl | CC(=O)c1ccc(NS(C)(=O)=O)cc1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 60 | [{"value": 60.0, "product": "C(C)(=O)C1=CC=C(C=C1)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "C(C)(=O)C1=CC=C(C=C1)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 84 | HOUR | Ex-100A: A solution of 4-aminoacetophenone (5.0 g, 37.0 mmol) and pyridine (3.0 mL) in anhydrous dichloromethane (300 mL) was treated with mesyl chloride (2.86 mL, 37.0 mmol). The reaction was stirred for 84 hours at room temperature under nitrogen, and then quenched with saturated NH4Cl solution (100 mL). The organic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | ClCCl | null | 84 | CC(=O)c1ccc(N)cc1.CS(=O)(=O)Cl>ClCCl>CC(=O)c1ccc(NS(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36f24c76b431434481f775654182115c | CC(=O)c1ccc(NS(C)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O>>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(NS(C)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)NS(=O)(=O)C.C(=O)C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1.C[O-].[Li+]>>CS(=O)(=O)NC1=CC=C(C=C1)C(/C=C/C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1)=O | [CH3:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([NH:29][S:30]([CH3:31])(=[O:32])=[O:33])[cH:34][cH:35]1.O=[CH:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:... | CC(=O)c1ccc(NS(C)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O | COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(NS(C)(=O)=O)cc1 | null | null | CO.O.CN(C)C=O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 15.5 | [{"value": 14.0, "product": "CS(=O)(=O)NC1=CC=C(C=C1)C(/C=C/C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.5, "product": "CS(=O)(=O)NC1=CC=C(C=C1)C(/C=C/C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A solution of N-(4-acetyl-phenyl)-methanesulfonamide (Ex-100A, 279.6 mg, 1.31 mmol) and 2-(4-formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-47D, 400 mg, 1.20 mmol) in DMF (5.25 mL) and MeOH (2.25 mL) was treated with lithium methoxide (182.2 mg, 4.8 mmol) and stirred for 5 hours at room temp. und... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | CO.O.CN(C)C=O | null | 5 | CC(=O)c1ccc(NS(C)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O>CO.O.CN(C)C=O>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(NS(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5821600eb019413e80b830f69e75ec23 | CC(=O)c1ccc(NS(C)(=O)=O)cc1.CI>>CC(=O)c1ccc(N(C)S(C)(=O)=O)cc1 | CI.CI.C(C)(=O)C1=CC=C(C=C1)NS(=O)(=O)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)C1=CC=C(C=C1)N(S(=O)(=O)C)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15]1.I[CH3:9]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([N:8]([CH3:9])[S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15]1 | CC(=O)c1ccc(NS(C)(=O)=O)cc1.CI | CC(=O)c1ccc(N(C)S(C)(=O)=O)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | c1ccccc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[c:7](:[c:8]):[c:9] | 64.1 | [{"value": 64.0, "product": "C(C)(=O)C1=CC=C(C=C1)N(S(=O)(=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.1, "product": "C(C)(=O)C1=CC=C(C=C1)N(S(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-101A: A solution of N-(4-acetyl-phenyl)-methanesulfonamide (Ex-100A, 2.0 g, 9.4 mmol) in anhydrous DMF (300 mL) was treated with potassium carbonate (2.59 g, 18.8 mmol), followed by the addition of methyl iodide (5.85 mL, 94 mmol). The reaction mixture refluxed for two hours and was then treated with more methyl iod... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | c1ccccc1 | HI | CN(C)C=O | null | null | CC(=O)c1ccc(NS(C)(=O)=O)cc1.CI>CN(C)C=O>CC(=O)c1ccc(N(C)S(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df81a26a90f141bbb39d4a69ebe31db6 | CC(=O)c1ccc(N(C)S(C)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O>>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(N(C)S(C)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)N(S(=O)(=O)C)C.C(=O)C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1.C[O-].[Li+]>>CS(=O)(=O)N(C1=CC=C(C=C1)C(/C=C/C1=CC(=C(OC(C(=O)O)(C)C)C=C1OC)C=1SC=CC1)=O)C | [CH3:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([N:29]([CH3:30])[S:31]([CH3:32])(=[O:33])=[O:34])[cH:35][cH:36]1.O=[CH:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[OH:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7]([CH3:8])([C... | CC(=O)c1ccc(N(C)S(C)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O | COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(N(C)S(C)(=O)=O)cc1 | null | null | CO.O.CN(C)C=O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | 6 | HOUR | A solution of N-(4-acetyl-phenyl)-N-methyl-methanesulfonamide (Ex-101A, 298 mg, 1.31 mmol) and 2-(4-formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-47D, 400 mg, 1.20 mmol) in DMF (5.25 mL) and MeOH (2.25 mL) was treated with lithium methoxide (182 mg, 4.8 mmol) and stirred for 6 hours at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | CO.O.CN(C)C=O | null | 6 | CC(=O)c1ccc(N(C)S(C)(=O)=O)cc1.COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1C=O>CO.O.CN(C)C=O>COc1cc(OC(C)(C)C(=O)O)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(N(C)S(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-607dcb3ea567495abab93b0af0ab0fe9 | CC(=O)c1ccc(N)cc1.CCCCOc1c(OCCCC)c(=O)c1=O.N>>CC(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1 | N.NC1=CC=C(C=C1)C(C)=O.C(CCC)OC=1C(C(C1OCCCC)=O)=O>>C(C)(=O)C1=CC=C(C=C1)NC=1C(C(C1N)=O)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:16][cH:17]1.CCCCO[c:9]1[c:10](OCCCC)[c:12](=[O:13])[c:14]1=[O:15].[NH3:11]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[c:10]([NH2:11])[c:12](=[O:13])[c:14]2=[O:15])[cH:16][cH:17]1 | CC(=O)c1ccc(N)cc1.CCCCOc1c(OCCCC)c(=O)c1=O.N | CC(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | ac1f8aec49256ed6f27f91bf581233412184be3db26dfdd16a6aef5efb0ad38a | cdf3a1ba3ca81a0239fc35d96fa8d0dbfe66a6ae926ab6c4e240fa8b31c8dee7 | O=c1cc(Nc2ccccc2)c1=O | C-C-C-C-O-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4](=[O;D1;H0:5]):[c;H0;D3;+0:6]:1-O-C-C-C-C.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10].[NH3;D0;+0:11]>>[NH2;D1;+0:11]-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4](=[O;D1;H0:5]):[c;H0;D3;+0:6]:1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 52.1 | [{"value": 52.0, "product": "C(C)(=O)C1=CC=C(C=C1)NC=1C(C(C1N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.1, "product": "C(C)(=O)C1=CC=C(C=C1)NC=1C(C(C1N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-102A: To a solution of 2.7 g (20 mmol) of 4′-aminoacetophenone in 90 mL of ethanol, 4.5 g (20 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (Aldrich) was added. The mixture was then heated to reflux overnight. A light yellow precipitate formed. To the reaction mixture, 20 mL (40 mmol) of ammonia (2.0 M in ethanol) w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | Primary amine.Secondary amine | C1=CC=C1 | C1=CC=C1 | c1ccccc1.C1=CC=C1 | HO- | C(C)O | null | null | CC(=O)c1ccc(N)cc1.CCCCOc1c(OCCCC)c(=O)c1=O.N>C(C)O>CC(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3e8acc5c7b94478861d04fd87697f50 | CC(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1 | C(C)(=O)C1=CC=C(C=C1)NC=1C(C(C1N)=O)=O.S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2.Cl.O([Li])C>>NC=1C(C(C1NC1=CC=C(C=C1)C(\C=C\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O)=O | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([NH:28][c:29]2[c:30]([NH2:31])[c:32](=[O:33])[c:34]2=[O:35])[cH:36][cH:37]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:... | CC(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1 | null | null | CN(C)C=O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccc(Nc2cc(=O)c2=O)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 5.6 | [{"value": 5.4, "product": "NC=1C(C(C1NC1=CC=C(C=C1)C(\\C=C\\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.6, "product": "NC=1C(C(C1NC1=CC=C(C=C1)C(\\C=C\\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | 3-(4-Acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione (Ex-102A, 0.46 g, 2 mmol), and 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde (Ex-3A, 0.596 g, 2 mmol) were dissolved in DMF (10 mL) under nitrogen, and 4.0 ml (4 mmol) of LiOMe (1.0 M in MeOH) was added. The mixture was stirred under nitrogen at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1.C1=CC=C1 | HO- | CN(C)C=O | null | null | CC(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>CN(C)C=O>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(Nc2c(N)c(=O)c2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd3f66696ce2493987252185d90a7bbb | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cccnc1>>COc1cc(OC)c(-c2cccnc2)cc1C=O | N1=CC(=CC=C1)B(O)O.BrC=1C(=CC(=C(C=O)C1)OC)OC>>COC1=C(C=O)C=C(C(=C1)OC)C=1C=NC=CC1 | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:16]([CH:17]=[O:18])[cH:15]1.OB(O)[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[cH:15][c:16]1[CH:17]=[O:18] | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cccnc1 | COc1cc(OC)c(-c2cccnc2)cc1C=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 68 | [{"value": 68.0, "product": "COC1=C(C=O)C=C(C(=C1)OC)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-104A: 2,4-Dimethoxy-5-pyridin-3-yl-benzaldehyde was prepared in a similar manner as described in Ex-3A from pyridine-3-boronic acid and 5-bromo-2,4-dimethoxybenzaldehyde, 68% yield. 1H-NMR (CDCl3) δ 10.33 (s, 1H), 8.71 (d, J=1 Hz, 1H), 8.51–8.53 (m, 1H), 7.81 (s, 1H), 7.74–7.78 (m, 1H), 7.27–7.31 (m, 1H), 6.52 (s, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | null | null | null | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cccnc1>>COc1cc(OC)c(-c2cccnc2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce21f1cc5c9b429bbe2772763daae429 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cccnc2)cc1C=O>>COc1cc(OC)c(-c2cccnc2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | COC1=C(C=O)C=C(C(=C1)OC)C=1C=NC=CC1.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N>>COC1=C(C=C(C(=C1)OC)C=1C=NC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N | [CH3:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([S:25]([NH2:26])(=[O:27])=[O:28])[cH:29][cH:30]1.O=[CH:17][c:16]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[cH:15][c... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cccnc2)cc1C=O | COc1cc(OC)c(-c2cccnc2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccnc2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 51 | [{"value": 51.0, "product": "COC1=C(C=C(C(=C1)OC)C=1C=NC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-pyridin-3-yl-benzaldehyde (Ex-104A) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Yellow solid, 51% yield, mp 253–255° C. 1H-NMR (DMSO-d6) δ 8.69 (d, J=1 Hz, 1H), 8.50 (d, J=4 Hz, 1H), 8.25 (d, J=9 Hz, 2H), 8.08 (d, J=15... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cccnc2)cc1C=O>>COc1cc(OC)c(-c2cccnc2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbb2cd7fd873464ea1dfd997d79efdb3 | COc1ccc(C(=O)CBr)cc1OC.N=C(N)C1CC1>>COc1ccc(-c2c[nH]c(C3CC3)n2)c(OC)c1 | BrCC(=O)C1=CC(=C(C=C1)OC)OC.C1(CC1)C(=N)N.[OH-].[Na+].C(C)O>>C1(CC1)C=1NC=C(N1)C1=C(C=C(C=C1)OC)OC | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:18]([O:16][CH3:17])[cH:15]1)[CH2:8]Br.[NH2:9][C:10]([CH:11]1[CH2:12][CH2:13]1)=[NH:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][nH:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[n:14]2)[c:15]([O:16][CH3:17])[cH:18]1 | COc1ccc(C(=O)CBr)cc1OC.N=C(N)C1CC1 | COc1ccc(-c2c[nH]c(C3CC3)n2)c(OC)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | cc99894fc8d1ba98aec90d22732c599393d600c687a9f647bce7a5ce089c2a0a | e51d27e1db406e8021512c89ccec77a0b648a313067b4504c213d6bb21eaed44 | c1ccc(-c2c[nH]c(C3CC3)n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6](-[#8:7]):[c;H0;D3;+0:8](-[O;H0;D2;+0:9]-[C;D1;H3:10]):[cH;D2;+0:11]:1.[NH2;D1;+0:12]-[C;H0;D3;+0:13](=[NH;D1;+0:14])-[C:15]1-[C:16]-[C:17]-1>>[#8:7]-[c:6]1:[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]2:[cH;D2;+0:1]:[nH;D2;+0:12]:[c;H0;D3;+0:13](-[C:15]... | 53 | [{"value": 53.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-105A: A solution of 2-bromo-1-(3,4-dimethoxy-phenyl)-ethanone (0.3 g, 1.16 mmol), cyclopropanecarboxamidine (0.14 g, 1.16 mmol) and sodium hydroxide (0.18 g, 4.5 mmol) in ethanol was refluxed overnight. The solvent was removed under reduced pressure, the residue taken up to water. The aqueous solution was then extra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ether.Primary amine | Ether | c1ccccc1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.C1CC1 | HBr | null | null | null | COc1ccc(C(=O)CBr)cc1OC.N=C(N)C1CC1>>COc1ccc(-c2c[nH]c(C3CC3)n2)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fcfe69e46057466bbea048d283df22b7 | COc1ccc(-c2c[nH]c(C3CC3)n2)c(OC)c1>>COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1C=O | C1(CC1)C=1NC=C(N1)C1=C(C=C(C=C1)OC)OC.COC(Cl)Cl>>C1(CC1)C=1NC=C(N1)C=1C(=CC(=C(C=O)C1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][nH:11][c:12]([CH:13]3[CH2:14][CH2:15]3)[n:16]2)[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][nH:11][c:12]([CH:13]3[CH2:14][CH2:15]3)[n:16]2)[cH:17][c:18]1[CH:19]=[O:20] | COc1ccc(-c2c[nH]c(C3CC3)n2)c(OC)c1 | COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1C=O | null | [Ti](Cl)(Cl)(Cl)Cl | null | Miscellaneous | OtherReaction | c25c41cbe22c67cd8a516e3f8fc0980bea758f12933876480aae20d5765822e2 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccc(-c2c[nH]c(C3CC3)n2)cc1 | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C:7]=[O;D1;H0:8]):[c:5]:[c:6] | null | [] | null | null | 4.5 | HOUR | Ex-105B: To a solution of 2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole (0.51 g, 2.09 mmol) was added dichloromethyl methyl ether (0.28 mL, 3.13 mmol) followed by addition of titanium tetrachloride (1.0M in dichloromethane, 8.4 mL, 8.4 mmol) dropwise at 0° C. The solution was allowed to warm up to ambient tempera... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]cn1.C1CC1 | Other | [Ti](Cl)(Cl)(Cl)Cl | null | 4.5 | COc1ccc(-c2c[nH]c(C3CC3)n2)c(OC)c1>[Ti](Cl)(Cl)(Cl)Cl>COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e886c98fe08c445a918a83a5ccce6da2 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O>>COc1cc(OCC(CO)CO)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | OCC(COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC)CO.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N>>OCC(COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)CO | [CH3:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([S:29]([NH2:30])(=[O:31])=[O:32])[cH:33][cH:34]1.O=[CH:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][OH:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O | COc1cc(OCC(CO)CO)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 72 | [{"value": 72.0, "product": "OCC(COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-(3-hydroxy-2-hydroxymethyl-propoxy)-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-50C) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Yellow solid, 72% yield, mp 191–192° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.29–8.32 (m, 3H), 8.09 (d, 1H, J=16... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCC(CO)CO)c(-c2cccs2)cc1C=O>>COc1cc(OCC(CO)CO)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-665a71c8df494a06987f1f3e49f3c7d1 | COC(=O)c1ccc(OC)cc1OC.NN>>COc1ccc(C(=O)NN)c(OC)c1 | COC(C1=C(C=C(C=C1)OC)OC)=O.NN>>COC1=C(C(=O)NN)C=CC(=C1)OC | CO[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][c:11]1[O:12][CH3:13])=[O:8].[NH2:9][NH2:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][NH2:10])[c:11]([O:12][CH3:13])[cH:14]1 | COC(=O)c1ccc(OC)cc1OC.NN | COc1ccc(C(=O)NN)c(OC)c1 | null | null | CO | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 78.1 | [{"value": 78.0, "product": "COC1=C(C(=O)NN)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "COC1=C(C(=O)NN)C=CC(=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-109A: A solution of 2,4-dimethoxy-benzoic acid methyl ester (4.24 g, 21.6 mmol) and hydrazine (3.4 mL, 108.1 mmol) in methanol (50 mL) was refluxed overnight. Solvent was removed under reduced pressure. The residue was re-dissolved in ethyl acetate. The solution of ethyl acetate was washed with saturated solution of... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccccc1 | HO- | CO | null | null | COC(=O)c1ccc(OC)cc1OC.NN>CO>COc1ccc(C(=O)NN)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8128df313cf4428687143d608ab819d6 | CC(C)CN=C=S.COc1ccc(C(=O)NN)c(OC)c1>>COc1ccc(C(=O)NNC(=S)NCC(C)C)c(OC)c1 | COC1=C(C(=O)NN)C=CC(=C1)OC.C(C(C)C)N=C=S>>COC1=C(C(=O)NNC(=S)NCC(C)C)C=CC(=C1)OC | [C:11](=[S:12])=[N:13][CH2:14][CH:15]([CH3:16])[CH3:17].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][NH2:10])[c:18]([O:19][CH3:20])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][NH:10][C:11](=[S:12])[NH:13][CH2:14][CH:15]([CH3:16])[CH3:17])[c:18]([O:19][CH3:20])[cH:21]1 | CC(C)CN=C=S.COc1ccc(C(=O)NN)c(OC)c1 | COc1ccc(C(=O)NNC(=S)NCC(C)C)c(OC)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 8cf946e319fae8c1c495a5ba581fadb7c0a794a27016cbc27d27b73b384322f9 | 05e50e03804c76371713bad755bbf759c85fdf6adcd49cbcec177943dc928c98 | c1ccccc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[NH2;D1;+0:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;D1;H0:5])-[NH;D2;+0:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[c:10] | 90 | [{"value": 90.0, "product": "COC1=C(C(=O)NNC(=S)NCC(C)C)C=CC(=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-109B: A solution of 2,4-dimethoxy-benzoic acid hydrazide (Ex-109A, 1.0 g, 5.1 mmol) and isobutyl-isothiocyanate (0.70 g, 6.1 mmol) in ethanol (30 mL) was refluxed for 8 hours. The precipitate was filtered, washed with ethanol, dried in vacuo to afford 1-(2,4-dimethoxy-benzoyl)amino-3-isobutyl-thiourea (1.43 g). Addi... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isothiocyanate | Acylhydrazine.Thiourea | null | null | c1ccccc1 | null | C(C)O | null | null | CC(C)CN=C=S.COc1ccc(C(=O)NN)c(OC)c1>C(C)O>COc1ccc(C(=O)NNC(=S)NCC(C)C)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fa6753b39494df987413a4807ef9f7e | COc1ccc(C(=O)NNC(=S)NCC(C)C)c(OC)c1>>COc1ccc(-c2nnc(S)n2CC(C)C)c(OC)c1 | COC1=C(C(=O)NNC(=S)NCC(C)C)C=CC(=C1)OC.[OH-].[Na+]>>COC1=C(C=CC(=C1)OC)C=1N(C(=NN1)S)CC(C)C | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][c:17]1[O:18][CH3:19])[NH:8][NH:9][C:10](=[S:11])[NH:12][CH2:13][CH:14]([CH3:15])[CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9][c:10]([SH:11])[n:12]2[CH2:13][CH:14]([CH3:15])[CH3:16])[c:17]([O:18][CH3:19])[cH:20]1 | COc1ccc(C(=O)NNC(=S)NCC(C)C)c(OC)c1 | COc1ccc(-c2nnc(S)n2CC(C)C)c(OC)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 22f8b57fd5b403bd11c09163332b57ccedc1fb3305169c1e6ba2b3a51fc964b9 | bd25a921a2c629db55acdd4e6573a984608495ab82bd2f024888ad689a9b3a51 | c1ccc(-c2nnc[nH]2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;H0;D1;+0:5])-[NH;D2;+0:6]-[C:7]-[C:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[#8:13]):[c:14]>>[#8:13]-[c:12](:[c:14]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[SH;D1;+0:5]):[n;H0;D3;+0:6]:1-[C:7]-[C:8]):[c:10]:[c:11] | 21.2 | [{"value": 21.2, "product": "COC1=C(C=CC(=C1)OC)C=1N(C(=NN1)S)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-109C: A solution of 1-(2,4-dimethoxy-benzoyl)amino-3-isobutyl-thiourea (Ex-109B, 0.5 g, 1.61 mmol) and sodium hydroxide (0.999M, 4.8 mL, 4.8 mmol) in ethanol (30 mL) was refluxed for one day. The solvent was removed under reduced pressure and the residue redissolved in ethyl acetate. The solution of ethyl acetate wa... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Thiourea | Aromatic thiol | null | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | HO- | C(C)O | null | null | COc1ccc(C(=O)NNC(=S)NCC(C)C)c(OC)c1>C(C)O>COc1ccc(-c2nnc(S)n2CC(C)C)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-422333bb2b134df086396efc34ef8002 | COc1ccc(-c2nnc(S)n2CC(C)C)c(OC)c1>>COc1ccc(-c2nncn2CC(C)C)c(OC)c1 | COC1=C(C=CC(=C1)OC)C=1N(C(=NN1)S)CC(C)C>>COC1=C(C=CC(=C1)OC)C1=NN=CN1CC(C)C | S[c:10]1[n:9][n:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][c:16]2[O:17][CH3:18])[n:11]1[CH2:12][CH:13]([CH3:14])[CH3:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9][cH:10][n:11]2[CH2:12][CH:13]([CH3:14])[CH3:15])[c:16]([O:17][CH3:18])[cH:19]1 | COc1ccc(-c2nnc(S)n2CC(C)C)c(OC)c1 | COc1ccc(-c2nncn2CC(C)C)c(OC)c1 | null | [Ni] | C(C)O | Reduction | OtherReaction | db7de21908ecd6716edb78816ffe6bcbd33b20d8cff701e0fc6337b3c0cbbd84 | 6dfa579c3c25232785e7dcb34dfc1e7688e0474e6615711d0e6a05188bc6f710 | c1ccc(-c2nnc[nH]2)cc1 | S-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4](-[c:5]):[#7;a:6]:1-[C:7]>>[C:7]-[#7;a:6]1:[cH;D2;+0:1]:[#7;a:2]:[#7;a:3]:[c:4]:1-[c:5] | 101.3 | [{"value": 100.0, "product": "COC1=C(C=CC(=C1)OC)C1=NN=CN1CC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.3, "product": "COC1=C(C=CC(=C1)OC)C1=NN=CN1CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-109D: To a solution of 5-(2,4-dimethoxy-phenyl)-4-isobutyl-4H-[1,2,4]triazole-3-thiol (Ex-109C, 0.1 g, 0.34 mmol) in ethanol (10 mL) was added wet Raney Ni (0.27 g, 4.6 mmol). The suspension of ethanol was refluxed overnight and then passed through a bed of Hyflo Super Gel and diatomaceous earth. The filtrate was co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | null | c1nc[nH]n1 | c1ncn[nH]1 | c1ccccc1.c1ncn[nH]1 | Other | [Ni].C(C)O | null | null | COc1ccc(-c2nnc(S)n2CC(C)C)c(OC)c1>[Ni].C(C)O>COc1ccc(-c2nncn2CC(C)C)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfb8c66bff4d48099a2e5ecf4d4ad3f8 | COc1ccc(-c2nncn2CC(C)C)c(OC)c1>>COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O | COC1=C(C=CC(=C1)OC)C1=NN=CN1CC(C)C.COC(Cl)Cl>>C(C(C)C)N1C(=NN=C1)C=1C(=CC(=C(C=O)C1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][cH:12][n:13]2[CH2:14][CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][cH:12][n:13]2[CH2:14][CH:15]([CH3:16])[CH3:17])[cH:18][c:19]1[CH:20]=[O:21] | COc1ccc(-c2nncn2CC(C)C)c(OC)c1 | COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O | null | [Ti](Cl)(Cl)(Cl)Cl | null | Miscellaneous | OtherReaction | c25c41cbe22c67cd8a516e3f8fc0980bea758f12933876480aae20d5765822e2 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccc(-c2nnc[nH]2)cc1 | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C:7]=[O;D1;H0:8]):[c:5]:[c:6] | 28 | [{"value": 28.0, "product": "C(C(C)C)N1C(=NN=C1)C=1C(=CC(=C(C=O)C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.8, "product": "C(C(C)C)N1C(=NN=C1)C=1C(=CC(=C(C=O)C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | Ex-109E: To a solution of 3-(2,4-dimethoxy-phenyl)-4-isobutyl-4H-[1,2,4]triazole (Ex-109D, 0.78 g, 2.98 mmol) was added dichloromethyl methyl ether (0.4 mL, 4.48 mmol) followed by addition of titanium tetrachloride (1.0M in dichloromethane, 9.0 mL, 9.0 mmol) over 10 min at 0° C. The reaction mixture was allowed to stir... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ncn[nH]1 | Other | [Ti](Cl)(Cl)(Cl)Cl | 0 | 8 | COc1ccc(-c2nncn2CC(C)C)c(OC)c1>[Ti](Cl)(Cl)(Cl)Cl>COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96724e89cdcb4f12bbae30db440eb7ce | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O>>COc1cc(OC)c(-c2nncn2CC(C)C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.C(C(C)C)N1C(=NN=C1)C=1C(=CC(=C(C=O)C1)OC)OC.C[O-].[Li+]>>C(C(C)C)N1C(=NN=C1)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)OC | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([S:28]([NH2:29])(=[O:30])=[O:31])[cH:32][cH:33]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][cH:12][n:13]2[CH2:14][CH:15]([CH3:16])[CH3:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][cH:12][n... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O | COc1cc(OC)c(-c2nncn2CC(C)C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | CN(C=O)C | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2nnc[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.62 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.18 g, 0.62 mmol) in N,N-dimethylformamide (9 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The solution was allowed to stir overnight. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ncn[nH]1.c1ccccc1 | HO- | CN(C=O)C | null | 8 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O>CN(C=O)C>COc1cc(OC)c(-c2nncn2CC(C)C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7a1710fbe634762b2d90eac36d3d924 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O>>COc1cc(OC)c(-c2nncn2CC(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | C[O-].[Li+].C(C)(=O)C1=CC=C(C(=O)O)C=C1.C(C(C)C)N1C(=NN=C1)C=1C(=CC(=C(C=O)C1)OC)OC.C[O-].[Li+]>>C(C(C)C)N1C(=NN=C1)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][cH:12][n:13]2[CH2:14][CH:15]([CH3:16])[CH3:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][n:11][cH:12][n:13]2[CH2:... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O | COc1cc(OC)c(-c2nncn2CC(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | CN(C=O)C | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2nnc[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To a solution of 4-acetyl-benzoic acid (0.12 g, 0.75 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.24 g, 0.83 mmol) in N,N-dimethylformamide (6 mL) was added lithium methoxide (1.0M in methanol, 3.0 mL, 3.0 mmol). The solution was allowed to stir overnight and additional lithium... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ncn[nH]1.c1ccccc1 | HO- | CN(C=O)C | null | 8 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2nncn2CC(C)C)cc1C=O>CN(C=O)C>COc1cc(OC)c(-c2nncn2CC(C)C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc0bededacff4f5c853c190677c0df9b | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1C=O>>COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.C1(CC1)C=1NC=C(N1)C=1C(=CC(=C(C=O)C1)OC)OC.C[O-].[Li+]>>C1(CC1)C=1NC=C(N1)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)OC | [CH3:20][C:21](=[O:22])[c:23]1[cH:24][cH:25][c:26]([S:27]([NH2:28])(=[O:29])=[O:30])[cH:31][cH:32]1.O=[CH:19][c:18]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][nH:11][c:12]([CH:13]3[CH2:14][CH2:15]3)[n:16]2)[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][nH:11][c:12]([CH:1... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1C=O | COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | CN(C=O)C | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2c[nH]c(C3CC3)n2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.59 mmol) and 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde (Ex-105B, 0.16 g, 0.59 mmol) in N,N-dimethylformamide (16 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The reaction mixture was allowed to stir for 18 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1c[nH]cn1.C1CC1.c1ccccc1 | HO- | CN(C=O)C | null | 18 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1C=O>CN(C=O)C>COc1cc(OC)c(-c2c[nH]c(C3CC3)n2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d24683324d84ddc92f92a2159bf2ee5 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C=O)C2)OC)OC.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N>>N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C2)/C=C/C(=O)C2=CC=C(C=C2)S(=O)(=O)N)OC)OC | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([S:28]([NH2:29])(=[O:30])=[O:31])[cH:32][cH:33]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][n:15][c:16]3[nH:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:1... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O | COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2nc3cccnc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 26 | [{"value": 26.0, "product": "N1=C(NC2=NC=CC=C21)C=2C(=CC(=C(C2)/C=C/C(=O)C2=CC=C(C=C2)S(=O)(=O)N)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 5-(3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-76A) with 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Yellow solid, 26% yield, mp>260° C. 1H-NMR (DMSO-d6) δ 8.73 (s, 1H), 8.31 (dd, J=1, 4 Hz, 1H), 8.26 (d, J=8 Hz, 2H), 8.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cnc2nc[nH]c2c1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1C=O>>COc1cc(OC)c(-c2nc3cccnc3[nH]2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cbd9458b4edf41a1a9c88fbbd2080d53 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2nc3ccccc3[nH]2)c(C=O)cc1-c1cccs1>>COc1cc(OCc2nc3ccccc3[nH]2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | N1C(=NC2=C1C=CC=C2)COC2=C(C=O)C=C(C(=C2)OC)C=2SC=CC2.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N>>N1C(=NC2=C1C=CC=C2)COC2=C(C=C(C(=C2)OC)C=2SC=CC2)/C=C/C(=O)C2=CC=C(C=C2)S(=O)(=O)N | [CH3:19][C:20](=[O:21])[c:22]1[cH:23][cH:24][c:25]([S:26]([NH2:27])(=[O:28])=[O:29])[cH:30][cH:31]1.O=[CH:18][c:17]1[c:5]([O:6][CH2:7][c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[nH:16]2)[cH:4][c:3]([O:2][CH3:1])[c:33](-[c:34]2[cH:35][cH:36][cH:37][s:38]2)[cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2nc3ccccc3[nH]2)c(C=O)cc1-c1cccs1 | COc1cc(OCc2nc3ccccc3[nH]2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCc1nc2ccccc2[nH]1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 56 | [{"value": 56.0, "product": "N1C(=NC2=C1C=CC=C2)COC2=C(C=C(C(=C2)OC)C=2SC=CC2)/C=C/C(=O)C2=CC=C(C=C2)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-(1H-benzoimidazol-2-ylmethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-113A) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Light orange solid, 56% yield, mp 235–237° C. (dec). 1H-NMR (300 MHz, DMSO-d6) δ 8.27 (s, 1H), 8.19 (d, 2H, ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2nc3ccccc3[nH]2)c(C=O)cc1-c1cccs1>>COc1cc(OCc2nc3ccccc3[nH]2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f7961d3b283411ba57f9e869a540bd0 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2ccccn2)c(C=O)cc1-c1cccs1>>COc1cc(OCc2ccccn2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCC1=NC=CC=C1.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCC1=NC=CC=C1 | [CH3:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([S:23]([NH2:24])(=[O:25])=[O:26])[cH:27][cH:28]1.O=[CH:15][c:14]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[cH:4][c:3]([O:2][CH3:1])[c:30](-[c:31]2[cH:32][cH:33][cH:34][s:35]2)[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:1... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2ccccn2)c(C=O)cc1-c1cccs1 | COc1cc(OCc2ccccn2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCc1ccccn1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OCC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-methoxy-2-(pyridin-2-ylmethoxy)-5-thiophen-2-yl-benzaldehyde (Ex-114A) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Yellow solid, 90% yield, mp 188–189° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.66 (d, 1H, J=3.6 Hz), 8.28 (s, 1H), 8.21 (d, 2H... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccncc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCc2ccccn2)c(C=O)cc1-c1cccs1>>COc1cc(OCc2ccccn2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57d4f5abb36947679528dda35b2d24d2 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCn2nnc3ccccc32)c(C=O)cc1-c1cccs1>>COc1cc(OCn2nnc3ccccc32)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | N1(N=NC2=C1C=CC=C2)COC2=C(C=O)C=C(C(=C2)OC)C=2SC=CC2.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N>>N1(N=NC2=C1C=CC=C2)COC2=C(C=C(C(=C2)OC)C=2SC=CC2)/C=C/C(=O)C2=CC=C(C=C2)S(=O)(=O)N | [CH3:19][C:20](=[O:21])[c:22]1[cH:23][cH:24][c:25]([S:26]([NH2:27])(=[O:28])=[O:29])[cH:30][cH:31]1.O=[CH:18][c:17]1[c:5]([O:6][CH2:7][n:8]2[n:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[cH:4][c:3]([O:2][CH3:1])[c:33](-[c:34]2[cH:35][cH:36][cH:37][s:38]2)[cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][n:8... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCn2nnc3ccccc32)c(C=O)cc1-c1cccs1 | COc1cc(OCn2nnc3ccccc32)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCn1nnc2ccccc21)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 56 | [{"value": 56.0, "product": "N1(N=NC2=C1C=CC=C2)COC2=C(C=C(C(=C2)OC)C=2SC=CC2)/C=C/C(=O)C2=CC=C(C=C2)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-(benzotriazol-1-ylmethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-115A) and 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Light yellow solid, 56% yield, mp 255° C. (dec). 1H-NMR (300 MHz, DMSO-d6) δ 8.21 (s, 1H), 8.09 (d, 3H, J=9.4 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2[nH]nnc2c1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OCn2nnc3ccccc32)c(C=O)cc1-c1cccs1>>COc1cc(OCn2nnc3ccccc32)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b835e6a7a7f3491a9842d10f3e2224da | COc1cc(OC)c(C=O)cc1Br.Cn1ccc2ccccc21>>COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.OO.CN1C=CC2=CC=CC=C12.[Li]C(C)(C)C.[OH-].[Na+].B(CC)(CC)CC>>COC1=C(C=O)C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:20]([CH:21]=[O:22])[cH:19]1.[cH:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1[CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2[CH3:18])[cH:19][c:20]1[CH:21]=[O:22] | COc1cc(OC)c(C=O)cc1Br.Cn1ccc2ccccc21 | COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C1CCOC1 | C-C Coupling | OtherReaction | 349907ad99649a935744aa3309bd56f4f7401595184a1a5ba68db576b2a68b22 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cc3ccccc3[nH]2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].[C;D1;H3:9]-[#7;a:10]1:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]:[#7;a:10]:1-[C;D1;H3:9]):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 25 | [{"value": 25.0, "product": "COC1=C(C=O)C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.4, "product": "COC1=C(C=O)C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Ex-116A: To a solution of N-methyl indole (1.3 g, 10 mmol) in 50 ml THF, t-BuLi (1.7 m in THF, 7.1 ml, 12 mmol) was slowly added at 0° C. under nitrogen. The mixture was stirred at room temperature for 1 hr, BEt3 (1.0 M in THF, 12 ml, 12 mmol) was added, and the mixture stirred for another 1 hr at room temperature. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1cc2ccccc2[nH]1 | c1ccccc1.c1cc2ccccc2[nH]1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1 | null | 1 | COc1cc(OC)c(C=O)cc1Br.Cn1ccc2ccccc21>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1>COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O |
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