Diisopropylethylamine → HCID 11606387, compound

Participants

Reaction Steps

To a solution of 60 mg (0.28 mmol) of 5-chloro-6-fluoro-1H-indole-7-carboxylic acid and 90 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.24 ml (1.4 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 99 mg (0.28 mmol) of (4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amine in 2 ml DMF were added. After stirring for 15 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. 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; EtOAc/heptane 1:19 then 1:9) followed by a second column chromatography (8 g silica gel; gradient DCM/heptane from 70% to 90% DCM) to give 69 mg white solid (44%). MS (ISP) 549.3 (M+H)+.

Provenance & Evidence