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

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.

1. customAfter the completion of the reaction
2. additionCelite was added to the diluted solution
3. stirringthe mixture was stirred at room temperature for additional 20 min
4. filtrationof filtering the reaction mixture through Celite
5. additionadding ethyl acetate to the residue
6. stirringstirring the mixture
7. filtrationfiltering the stirred mixture through Celite
8. customthe solvent was removed by distillation under the reduced pressure
9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1)

ORD record

ord-9e8ed757848742fd823b704955138119

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662841B2