Diisopropylethylamine → 5-Chloro-6-fluoro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amide

Participants

Reaction Steps

To a solution of 200 mg (0.94 mmol) 5-chloro-6-fluoro-1H-indole-7-carboxylic acid and 300 mg of TBTU (0.94 mmol) in 15 ml DMF, were added 0.8 ml (4.68 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 329 mg (0.94 mmol) (4-tert-butyl-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 17 h at rt, the reaction mixture was diluted with 160 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (90 g silica gel; diethylether/heptane 1:1) to give 130 mg off-white foam (23%). MS (ISP) 547.4 (M+H)+.

Provenance & Evidence