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

A solution of ethyl 2-bromoimidazo[5,1-b] thiazole-7-carboxylate (84 mg, 0.31 mmol) in tetrahydrofuran (7 ml) was cooled to −50° C. A toluene solution of diisobutylaluminium hydride (1.01 M solution; 1.06 ml, 1.07 mmol) was added dropwise to the cooled solution, and the mixture was stirred at the same temperature for 15 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 1.5 hr and 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→30:1) to give 2-bromo-7-hydroxymethylimidazo[5,1-b]thiazole (44 mg, 61%) as a white solid and 2-bromoimidazo[5,1-b]thiazole-7-carbaldehyde (19 mg, 26%) as a white solid.

1. customAfter the completion of the reaction
2. stirringthe mixture was stirred at room temperature for 1.5 hr
3. extractionwas extracted with ethyl acetate (7 ml×3)
4. washThe organic layer was washed with saturated brine
5. dry with materialwas then dried over anhydrous sodium sulfate
6. customThe solvent was removed by distillation under the reduced pressure
7. customthe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1→30:1)

ORD record

ord-1a64fcb5943c42b8a58fea7bfc244133

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662841B2