Oxalyl chloride → HCID 58488517, compound

Participants

Reaction Steps

To a suspension of 5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid (7.7 g, 27 mmol) in dichloromethane (60 ml) was added oxalyl chloride (5.1 ml, 59 mmol). The mixture was stirred at room temperature for 2.0 h, after which time the solvent was removed on a rotary evaporator. To this brown residue was added 4-(methanesulfonyl)aniline hydrochloride (5.8 g, 28 mmol), tetrahydrofuran (THF) (80 ml) and diisopropylethylamine (DIEA) (14 ml, 80 mmol). The solution was stirred at room temperature for 2.0 h. The reaction mixture was concentrated and to the residue was added 2N HCl (80 ml) and water (80 ml) and resulting suspension was stirred for 30 min. The solid was filtered and washed with water and diisopropyl ether (IPE) to give the title compound as a white solid (11 g, 90%).

Provenance & Evidence