1H-Indole-7-carboxylic acid → [Rac]-1h-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amide

Participants

Reaction Steps

To a solution of 50 mg (0.31 mmol) of 1H-indole-7-carboxylic acid and 97 mg of TBTU (0.31 mmol) in 4 ml DMF, were added 0.27 ml (1.55 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 99 mg (0.31 mmol) of [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine were added. After stirring for 17 h at rt, the reaction mixture was diluted with 40 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 (8 g silica gel; heptane/EtOAc 2:1) to give 89 mg (61%) of a white solid. MS (ISP) 461.4 (M+H)+.

Provenance & Evidence