Diisopropylethylamine → HCID 11606213, compound

Participants

Reaction Steps

To a solution of 185 mg (0.87 mmol) 5-chloro-6-fluoro-1H-indole-7-carboxylic acid and 278 mg of TBTU (0.87 mmol) in 13 ml DMF, were added 0.74 ml (4.33 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 290 mg (0.87 mmol) (4-tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 17 h at rt, the reaction mixture was diluted with 140 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 two successive column chromatographies (90 g silica gel; diethylether/heptane 1:1; then 8 g silica gel; DCM/heptane 70:30 to 90:10) to give 125 mg white foam (27%). M (EI) 530.2 (M)+.

Provenance & Evidence