Toluene → 2-Bromo-7-hydroxymethylimidazo[5,1-b]thiazole

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate (31 mg, 0.12 mmol) in dichloromethane (8 ml) was cooled to −100° C. Thereafter, a toluene solution of diisobutylaluminium hydride (1.01 M solution; 0.4 ml, 0.4 mmol) was added dropwise to the cooled solution. The mixture was stirred at −100° C. for 50 min and then at −80° C. for 15 min. After the completion of the reaction, a saturated aqueous potassium sodium tartrate solution was added to the reaction solution, and the mixture was stirred at room temperature for one hr and was extracted with ethyl acetate (8 ml×3). The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure to give 2-bromo-7-hydroxymethylimidazo[5,1-b]thiazole (26 mg, 95%) as a white solid.

Provenance & Evidence