Triethylamine → 3-{2-[2-(4-bromophenyl)pyrrolidin-1-yl]ethyl}-2-methyl-1H-indole

Participants

Reaction Steps

To a solution of 2-(4-bromo-phenyl)-pyrrolidine (326 mg, 1.44 mmol) in dichloromethane (20 mL) were added (2-methyl-1H-indol-3-yl)-acetaldehyde (250 mg, 1.44 mmol), triethylamine (0.603 mL, 4.33 mmol) and a solution of titanium (IV) chloride in dichloromethane (0.720 mL, 1 M, 0.72 mmol), and the resulting mixture was stirred at room temperature. The reaction mixture was treated with sodium cyanoborohydride (286 mg, 4.32 mmol), stirred for 2 h, basified to pH 13 with an aqueous 5 N sodium hydroxide solution, and extracted with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated to provide a crude product, which was purified on silica gel column chromatography to give 3-{2-[2-(4-bromo-phenyl)-pyrrolidin-1-yl]-ethyl}-2-methyl-1H-indole (630 mg, 99% yield). LCMS (m/z): 384.84 (M+1).

Provenance & Evidence