Diisopropylethylamine → HCID 118074746, compound

Participants

Reaction Steps

To a mixture of 3-{2-[(tert-butoxycarbonyl)amino]ethyl}-5-methoxy-1H-indole-2-carboxylic acid (500 mg), diisopropylethylamine (1.28 mL), methylamine hydrochloride (303 mg), and N,N-dimethyl formamide (10.0 mL) was added 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (853 mg), followed by stirring at room temperature overnight. To the mixture was added ice water, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1) to obtain tert-butyl {2-[5-methoxy-2-(methylcarbamoyl)-1H-indol-3-yl]ethyl}carbamate (520 mg) as a white solid.

Provenance & Evidence