Triethylamine → N-methoxy-N-methyl-1H-indole-2-carboxamide

Participants

Reaction Steps

A mixture of 1H-indole-2-carboxylic acid (from Aldrich, 2.5 g, 16 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (7.6 g, 20 mmol) and triethylamine (11 mL, 78 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 10 minutes. N,O-Dimethylhydroxylamine hydrochloride (2.0 g, 20 mmol) was added and the resulting suspension was stirred at room temperature for 2 hours. The mixture was quenched with water, extracted with EtOAc. The combined organic layers were dried over Na2SO4, concentrated and purified on silica gel (eluting with 0-50% EtOAc in hexane) to give the desired product (2.7 g, 85%). LCMS calculated for C11H13N2O2(M+H)+: m/z=205.1. Found: 205.1.

Provenance & Evidence