4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxyphenyl]acryloyl}-N-pyridin-2-yl-benzenesulfonamide → 4-{3E-[5-(1H-Indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}-N-pyridin-2-ylbenzenesulfonamide
反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]#[C:9][C:10]1[C:11]([O:38][CH3:39])=[CH:12][C:13]([O:36][CH3:37])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1>C(#N)C.[Pd](Cl)Cl>[NH:1]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:8]=[C:9]1[C:10]1[C:11]([O:38][CH3:39])=[CH:12][C:13]([O:36][CH3:37])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1参加物
4
実験手順
A suspension of 4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxyphenyl]acryloyl}-N-pyridin-2-ylbenzenesulfonamide (Ex-57A, 735 mg, 1.36 mmol) in acetonitrile (100 mL) was purged with nitrogen for 10 minutes. Palladium(II) chloride (24 mg, 0.14 mmol) was added and the reaction mixture was refluxed for 3.5 hrs. The cooled reaction mixture was stirred with 3-mercaptopropyl functionalized silica gel (500 mg) for 5 minutes, filtered, and concentrated. The crude material was purified by column chromatography (2% MeOH in dichloromethane) to give 320 mg (44%) of the title compound as a red solid, mp 206–208° C. 1H-NMR (300 MHz, DMSO-d6) 11.13 (br s, 1H), 8.31 (s, 1H), 8.19 (d, 2H, J=7.80 Hz), 8.05 (m, 3H), 7.94 (br s, 1H), 7.82 (d, 1H, J=15.0 Hz), 7.74 (t, 2H, J=7.2 Hz), 7.49 (d, 1H, J=8.1 Hz), 7.41 (d, 1H, J=7.5 Hz), 7.21 (d, 1H, J=8.4 Hz), 7.05 (t, 1H, J=7.5 Hz), 6.95 (m, 2H), 6.82 (s, 2H), 4.03 (s, 3H), 3.98 (s, 3H). HRMS (ESI) Calcd. for C30H25N3O5S: (M+H)+; Found: 540.1576.