Cornforth reagent → 2-Bromoimidazo[5,1-b]thiazole-7-carbaldehyde

A suspension of 2-bromo-7-hydroxymethylimidazo [5,1-b]thiazole (24 mg, 0.10 mmol) in dichloromethane (3.5 ml) was added to a solution of pyridinium dichromate (47 mg, 0.13 mmol) in dichloromethane (1.5 ml), and the mixture was stirred at room temperature for 5 hr. After the completion of the reaction, the reaction solution was diluted with ethyl acetate, 4A molecular sieves were added thereto, and the mixture was stirred at room temperature for 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 (11 mg, 47%) as a white solid.

1. customAfter the completion of the reaction
2. additionwere added
3. stirringthe mixture was stirred at room temperature for 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-401846e836df4b4e92b59cf8a61f24d1

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662841B2