Tin tetrachloride → 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Participants

Reaction Steps

To a solution of 1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide (800 mg, 3.7 mmol) and 2-chloronicotinoyl chloride (95 mg, 5.4 mmol) in dry benzene (10 mL) at 0° C. was added dropwise a solution of tin (IV) chloride (1.75 g) in benzene (5 mL). The mixture was allowed to warm up slowly to room temperature and stirred for overnight. The reaction was concentrated, diluted with ethyl acetate, washed with water, 1N NaOH, brine, dried and concentrated. The residue was purified on a silica gel column to give 458 mg (35%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide.

Provenance & Evidence