Ethylamine hydrochloride → N-ethyl-1H-pyrrole-3-carboxamide

Participants

Reaction Steps

DIPEA (10.4 mL, 7.8 g, 60 mmol) was added to a solution of 1H-pyrrole-3-carboxylic acid (2.2 g, 20 mmol) and ethylamine hydrochloride (2.5 g, 30 mmol) in DMF (50 mL) at 0° C. Stirring for 20 min, HATU (9.9 g, 26 mmol) was added at 0° C. The reaction mixture was stirred overnight at room temperature, diluted with EtOAc (300 mL), washed with H2O (3×30 mL) and dried over Na2SO4. The crude product was purified by MPLC using EtOAc on silica gel to give 4.0 mL of a solution of the desired product in DMF. Small amount of the desired product was purified again by MPLC using EtOAc on silica gel for NMR. 1H NMR (400 MHz, CHLOROFORM-D) δ 1.22 (t, J=7.23 Hz, 3 H), 3.39-3.51 (m, 2 H), 5.84 (s, 1 H), 6.37-6.42 (m, 1 H), 6.77 (dd, J=4.98, 2.44 Hz, 1 H), 7.30-7.39 (m, 1 H), 8.85 (t, 1 H).

Provenance & Evidence