Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate → methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

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Reaction Steps

To a suspension of 6 g of 1H-imidazo[4,5-c]pyridine in 300 ml of anhydrous dichloromethane is slowly added a solution of 4.8 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate. The reaction mixture is stirred for 14 h at room temperature. The solvent is removed under reduced pressure and the residue is purified by flash chromatography [silica gel, elution gradient of toluene/ethyl acetate/acetic acid, 80/20/1 (v/v/v)] to 30/70/1 (v/v/v) to give the separated title compounds along with a small fraction of the isomeric mixture.

Provenance & Evidence