Sodium Acetate → 2-Bromoimidazo[5,1-b]thiazole-7-carbaldehyde

Participants

Reaction Steps

A solution of 2-bromo-7-hydroxymethylimidazo [5,1-b]thiazole (27 mg, 0.11 mmol) in dichloromethane (3.5 ml) was added to a suspension of pyridinium chlorochromate (38 mg, 0.18 mmol) and sodium acetate (4.8 mg, 0.06 mmol) in dichloromethane (1.5 ml). The mixture was stirred at room temperature for 30 min. After the completion of the reaction, the reaction solution was diluted with diethyl ether. Celite was added to the diluted solution, and the mixture was stirred at room temperature for additional 20 min. The procedure consisting of filtering the reaction mixture through Celite, adding ethyl acetate to the residue, stirring the mixture, and filtering the stirred mixture through Celite was repeated a few times. The filtrates were combined, and the solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1) to give 2-bromoimidazo[5,1-b]thiazole-7-carbaldehyde (5 mg, 20%) as a white solid.

Provenance & Evidence