Sodium Hydroxide → 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide

Participants

Reaction Steps

To a solution of 1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide (1.56 g, 7.6 mmol) and 2-chloronicotinoyl chloride (1.925 g, 10.9 mmol) in benzene (15 mL) at 0° C. was added dropwise a solution of tin (IV) chloride (3.5 g) in dry benzene (5 mL). The mixture was allowed to warm up slowly to room temperature and stirred for 4 hours. The reaction was added with NaOH (100 mL) and extracted with ethyl acetate, washed with brine (2×), dried and concentrated. The residue was purified on a silica gel column to give 477 mg (18%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide.

Provenance & Evidence