Tin tetrachloride → ethyl 5-(2-chloronicotinoyl)-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

A solution of tin (IV) chloride (3.72 g, 5 mmol) in benzene (10 mL) was added dropwise to a mixture of 2-chloronicotinoyl chloride (2.02 g, 11 mmol) and 1H-pyrrole-2-carboxylic acid ethyl ester (0.73 g; prepared as discussed below) in dry benzene (12 mL) at 0° C. The reaction was allowed to warm up slowly to room temperature and stirred 4 hours. The reaction was concentrated, the residue was dissolved in ethyl acetate and washed with brine, dried and concentrated to give 1.53 g of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ethyl ester as a brown solid.

Provenance & Evidence