Diisopropylethylamine → [Rac]-5-chloro-1h-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amide

Participants

Reaction Steps

To a solution of 31 mg (0.16 mmol) of 5-chloro-1H-indole-7-carboxylic acid and 51 mg of TBTU (0.16 mmol) in 2 ml DMF, were added 0.14 ml (0.79 mmol) of N,N-diisopropyl-ethyl amine. After stirring for 5 min at rt, 81 mg (0.16 mmol) of [rac]-(4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amine were added. After stirring for 17 h at rt, the reaction mixture was diluted with 20 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 38 mg (44%) of a light yellow foam. MS: 528 (M).

Provenance & Evidence