[CH3:1][N:2]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[CH:15]2)[C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=O.B.O1CCCC1.CO>O1CCCC1>[CH3:1][N:2]([CH2:3][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[CH:15]2To a solution of N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-carboxamide (150 mg) in tetrahydrofuran (10 mL) was added borane-tetrahydrofuran complex (1.0 M tetrahydrofuran solution, 10 mL). The reaction mixture was stirred with heating under reflux for 1 hr. The reaction mixture was cooled to room temperature, and methanol (5 mL) was added. The reaction mixture was stirred with heating under reflux for 1 hr, and the reaction mixture was concentrated. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (55 mg, yield 38%) as a yellow oil. M+1=326.
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