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

A solution of ethyl 2-bromoimidazo[5,1-b] thiazole-7-carboxylate (101 mg, 0.37 mmol) in dichloromethane (5 ml) was cooled to −50° C. A toluene solution of diisobutylaluminium hydride (1.01 M solution; 1.1 ml, 1.1 mmol) was then added dropwise to the cooled solution, and the mixture was stirred at the same temperature for 10 min. After the completion of the reaction, a saturated aqueous potassium sodium tartrate solution was added thereto, and the mixture was stirred at room temperature for one hr and was extracted with ethyl acetate (7 ml×3). The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure to give 2-bromo-7-hydroxymethylimidazo[5,1-b]thiazole (85 mg, 99%) as a white solid.

1. customAfter the completion of the reaction
2. stirringthe mixture was stirred at room temperature for one hr
3. extractionwas extracted with ethyl acetate (7 ml×3)
4. washThe organic layer was washed with saturated brine
5. dry with materialwas dried over anhydrous sodium sulfate
6. customthe solvent was removed by distillation under the reduced pressure

ORD record

ord-b9e31d92e2654e489578c86435f03f29

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662841B2