Acetic Acid → Indole

反応式

CC(=O)CCC(=O)C.CN1CC=C([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22](N)[CH:23]=3)[N:18](S(C3C=CC=CC=3)(=O)=O)[CH:17]=2)CC1.C(O)(=O)C>C(O)C>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17]1

参加物

実験手順

Hexane-2,5-dione (2 mL) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indol-5-amine (300 mg, 0.82 mmol) in ethanol (50 mL). Acetic acid (2 mL) was added, and the resulting solution was stirred at room temperature overnight. The solvent was concentrated, followed by column chromatography purification using a 1:10 methanol/dichloromethane solvent system provided 30 mg (8%) of 5-(2,5-dimethyl-1H-pyrrol-1-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-phenylsulfonyl)-1H-indole as a yellow solid. 1H NMR (CDCl3) δ 8.05 (d, 1H), 7.95 (d, 2H), 7.62 (s, 1H), 7.50 (d, 2H), 7.26 (2H), 6.84 (d, 2H), 6.11 (s, 1H), 5.90 (s, 2H), 3.46 (d, 2H), 3.07 (t, 2H), 2.74 (s, 2H), 2.62 (s, 2H), 1.98 (s, 6H). LC/MS (EI) tR 2.46, m/z 446.0 (M++1)