Water → HCID 69020655, compound

Participants

Reaction Steps

A solution of 3-(4-bromo-phenyl)-4-cyano-1H-pyrrole-2-carboxylic acid ethyl ester (41.59 g, 0.130 mol) in DMSO (400 mL) is treated with K2CO3 (19.76 g, 0.143 mol). The resulting solution is allowed to stir at room temperature for several minutes, and then treated with iodomethane (9.75 mL, 0.156 mol). The resulting reaction mixture is allowed to stir under nitrogen at room temperature overnight, then poured into water (2,000 mL) and extracted with EtOAc (4×500 mL each). The combined organics are washed with water (2×1,000 mL each), brine (700 mL), dried over anhydrous MgSO4, filtered, then concentrated in vacuo to afford an off-white solid. The solid is dissolved in a minimum amount of EtOAc, then treated with excess hexanes, causing a solid to crash out. The solid is recovered by vacuum filtration, washed with hexanes, and dried under vacuum filtration to afford the final title compound, 3-(4-bromo-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester, (33.45 g, 77% yield) as a off-white solid: 1H NMR (500 MHz; CDCl3) δ 1.07 (t, 3H), 3.97 (s, 3H), 4.13 (q, 2H), 7.23 (s, 1H), 7.26 (d, 2H), 7.52 (d, 2H); MS(ES): m/z 333.1 (M+H+). Anal. Calcd. for C15H13BrN2O2: C 54.07; H 3.93; N 8.40; Br 23.98. Found C 53.91; H 3.93; N 8.35; Br 24.06.

Provenance & Evidence