Tributyltin Chloride → 5-Formylaminomethyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Temperature

0 °C

A solution of 9 06 mg of 5-formylaminomethyl imidazo[5,1-b]-thiazole in a mixed solvent of 30 ml of THF and 6 ml of HMPA was cooled to −78° C. under the atmosphere of argon, and 10.9 ml of a 1.6 N solution of n-butyl lithium/n-hexane was added dropwise at an internal temperature of −70-−65° C. After the reaction mixture was stirred at the same temperature for 1 hour, 1.63 ml of tri-n-butylstannyl chloride was added, and the mixture was further stirred at the same temperature for 1 hour and for 2 hours during which the temperature was raised up to 0° C. 100 ml of a semi-saturated aqueous ammonium chloride solution was added to the reaction mixture, and extracted with 100 ml of diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give the title compound in an amount of 1.59 g.

1. additionwas added dropwise at an internal temperature of −70-−65° C
2. stirringthe mixture was further stirred at the same temperature for 1 hour and for 2 hours during which the temperature
3. extractionextracted with 100 ml of diethyl ether
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was removed under reduced pressure
6. customThe residue thus obtained
7. customwas purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

ORD record

ord-2d7ebc4127214c5cadea07d99f2a62a2

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310056B1