Phosphate → 7-Acetyl-3-methyl-2-(tri-n-butylstannyl)imidazo-[5,1-b]thiazole

A 1.0 N lithiumbis(trimethylsilyl)amide/n-hexane solution: (2.2 ml) was added dropwise to a solution of 0.360 g of 7-acetyl-3-methylimidazo[5,1-b]thiazole in THF (20 ml) at −70° C. The mixture was stirred for 15 min. A 1.6 N n-butyllithium/n-hexane solution (2.8 ml) was added dropwise to the reaction solution at the same temperature. The mixture was stirred for one hr. A solution (4 ml) of 0.846 g of tri-n-butylstannyl chloride in THF was added dropwise to the reaction solution. The mixture was stirred at −40° C. for 30 min. The reaction solution was added under ice cooling to a mixed solution composed of ether (50 ml) and 0.2 N phosphate buffer (pH 7) (50 ml) with thorough stirring. The organic layer was separated, washed with 0.2 N phosphate buffer (pH 7) (30 ml), and dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was subjected to separation and purification by flash column chromatography on silica gel (ethyl acetate) to give 0.752 g of the title compound.

1. stirringThe mixture was stirred for one hr
2. stirringThe mixture was stirred at −40° C. for 30 min
3. additionThe reaction solution was added under ice cooling to a mixed solution
4. customThe organic layer was separated
5. washwashed with 0.2 N phosphate buffer (pH 7) (30 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was removed by distillation
8. customThe residue was subjected to separation and purification by flash column chromatography on silica gel (ethyl acetate)

ORD record

ord-b9dbb1aea8664b028b8991e42bbe2e41

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677331B2