Trimethylaluminum → 1h-Pyrrolo[2,3-c]pyridine-7-carboxylic acid(4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amide

Participants

Reaction Steps

Trimethylaluminum solution (2 M in heptane, 0.14 mL, 0.28 mmol) was added at RT to a solution of (4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amine (100 mg, 0.28 mmol) in dichloromethane (0.7 mL), then after 15 min a solution of 1H-pyrrolo[2,3-c]pyridine-7-carboxylic acid methyl ester (50 mg, 0.14 mmol) in dichloromethane was added. After 2 h the reaction mixture was partitioned between ethyl acetate and 2 M aq. hydrochloric acid solution. The organic layer was washed with brine, dried (MgSO4), evaporated, and chromatographed (SiO2, heptane/ethyl acetate gradient), to afford the title compound (70 mg, 50%). White foam, MS (ISP) 498.3 (M+H)+.

Provenance & Evidence