4-Methylmorpholine → 5-Chloro-1H-indole-7-carboxylic acid (4-tert-butyl-2-chloro-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide

Participants

Reaction Steps

106 mg (1.05 mmol) of N-methyl morpholine and then 199 mg (0.53 mmol) of HBTU were added to 68 mg (0.35 mol) of 5-chloro-1H-indol-7-carboxylic acid and 136 mg (0.39 mmol) of (4-tert-butyl-2-chloro-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amine dissolved in 3.5 ml DMF at rt under nitrogen. The reaction mixture was stirred at rt for 3 h. Water was added and the reaction mixture was extracted twice with EtOAc. The combined organic layers were washed once with 1N aqueous HCl solution, once with saturated aqueous NaHCO3 solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (20 g silica gel, heptane/EtOAc 7:3) to yield 160 mg (92%) product as a light yellow foam. MS (EI) 496.1 (M)+.

Provenance & Evidence