Diisopropylethylamine → [Rac]-5-chloro-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 (0.26 mmol) of 5-chloro-1H-indole-7-carboxylic acid and 80 mg of TBTU (0.26 mmol) in 4 ml DMF, were added 0.22 ml (1.28 mmol) of N,N-diisopropyl-ethyl amine. After stirring for 5 min at rt, 81 mg (0.26 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 30 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 60 mg (42%) of a light yellow solid. MS (ISP): 495.4 (M+H)+.

Provenance & Evidence