Diisopropylethylamine → N-methyl-1H-pyrrole-3-carboxamide

Participants

Reaction Steps

DIPEA (284 mg, 381 uL, 2.2 mmol) was added to a solution of 1H-pyrrole-3-carboxylic acid (111 g, 1.0 mmol) and methylamine hydrochloride (222 mg, 3.3 mmol) in DMF (10 mL) at 0° C. Stirring for 20 min, HATU (570 g, 1.5 mmol) was added at 0° C. The reaction mixture was stirred overnight at room temperature, diluted with EtOAc (100 mL), washed with H2O (3×10 mL) and dried over Na2SO4. The crude product was purified by MPLC using EtOAc on silica gel. Yield: 57 mg (46%). 1H NMR (400 MHz, CHLOROFORM-D) δ 2.89 (s, 3 H), 5.89 (s, 1 H), 6.36-6.44 (m, 1 H), 6.75-6.79 (m, 1 H), 7.34-7.40 (m, 1 H).

Provenance & Evidence