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

Temperature

-100 °C

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.

1. waitat −80° C. for 15 min
2. customAfter the completion of the reaction
3. stirringthe mixture was stirred at room temperature for one hr
4. extractionwas extracted with ethyl acetate (8 ml×3)
5. washThe organic layer was washed with saturated brine
6. dry with materialwas dried over anhydrous sodium sulfate
7. customThe solvent was removed by distillation under the reduced pressure

ORD record

ord-b6e82ee0106541feb9e0ea2c37401fe9

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662841B2