Tributyltin Chloride → 7-(Pyridin-3-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Temperature

-50 °C

Tri-n-butylstannyl chloride (0.841 ml) and 2.95 ml of a 1.0 N lithium bis(trimethylsilyl)amide/THF solution were added to a solution of 520 mg of 7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazole in 25 ml of THF at −60° C. under an argon atmosphere, and the mixture was stirred for 20 min. The temperature of the mixture was raised to −50° C., 1.0 ml of a 1.0 N lithium bis(trimethylsilyl)amide/THF solution was added thereto, and the mixture was stirred for 30 min. The temperature of the mixture was raised to −40° C., 0.5 ml of a 1.0 N lithium bis(trimethylsilyl)amide/THF solution was added thereto, and the mixture was stirred for 30 min. An aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1→ethyl acetate only) to give 712 mg of the title compound.

1. stirringthe mixture was stirred for 30 min
2. temperatureThe temperature of the mixture was raised to −40° C.
3. stirringthe mixture was stirred for 30 min
4. extractionthe mixture was extracted with ethyl acetate
5. washby washing with brine
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. customThe solvent was then removed by distillation
8. customthe residue was purified by column chromatography on silica gel (hexane

ORD record

ord-2001be10c4314a4a95c5fde4c48fadd7

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06908913B2