Aniline → HCID 58172084, compound

Participants

Reaction Steps

A reaction flask equipped with a nitrogen line and a stir bar was charged with a solution of 3-(3-benzyloxycarbonylamino-propyl)-1H-indole-2,5-dicarboxylic acid 2-ethyl ester (64 mg, 0.15 mmol) in dichloromethane (2 mL) and DMSO (1 mL). 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (37.5 mg, 0.19 mmol) and 1-hydroxybenzotriazole hydrate (26.5 mg, 0.19 mmol) were added. The reaction mixture was stirred for 0.5 h. Aniline (20.5 microL, 0.23 mmol) was added and stirring continued for 48 h. The reaction mixture was diluted with ethyl acetate and washed in turn with 1N HCl. and saturated sodium carbonate. The organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated and the resulting oil was purified by flash chromatography with 50-100% ethyl acetate/hexane to give 3-(3-benzyloxycarbonylamino-propyl)-5-phenylcarbamoyl-1H-indole-2-carboxylic acid ethyl ester (44 mg, 58%).

Provenance & Evidence