Ammonium Chloride → 2-Bromoimidazo[5,1-b]thiazole-7-carbaldehyde

Temperature

-40 °C

A solution of 2-bromoimidazo[5,1-b]thiazole-7-carboxylic acid chloride (103 mg, 0.39 mmol) in diglim (10 ml) was cooled to −78° C. A solution of tri-t-butoxyaluminumlithium hydride(237 mg, 0.94 mmol) in diglim (6 ml) was added dropwise to the cooled solution, and, while gradually raising the temperature to −40° C., the mixture was stirred for 6 hr. After the completion of the reaction, a saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate (7 ml×3). The organic layer was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and 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 (28 mg, 31%) as a white solid.

1. customAfter the completion of the reaction
2. extractionthe mixture was extracted with ethyl acetate (7 ml×3)
3. washThe organic layer was washed with saturated brine
4. dry with materialwas then dried over anhydrous sodium sulfate
5. customThe solvent was removed by distillation under the reduced pressure
6. customthe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1)

ORD record

ord-43bc54c92c8b4cc9b8bb7fa85c852c4c

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662841B2