Tributyltin Chloride → Tributyl-[4-methyl-2-(3-pyridyl)thiazol-5-yl]stannane

Participants

Reaction Steps

In a dry flask under argon, 5-bromo-4-methyl-2-(3-pyridyl)thiazole (15.00 g, 55.85 mmol) was dissolved in THF (140 mL), and with cooling to keep the temperature at 25°-30° C., treated dropwise with i-PrMgCl.LiCl (TurboGrignard, 60 mL, 78.19 mmol,). The resulting mixture was allowed to stir at ambient temperature for 1 hour. The reaction mixture was then cooled to 10° C., and tri-n-butyl tin chloride (19 mL, 67.02 mmol) was added over 5 min. The reaction was stirred for 30 min at ambient temperature and then at reflux (66° C.) for 18 hours. The reaction mixture was quenched with saturated NH4Cl solution and diluted with ethyl acetate. Then aqueous layer was extracted 3 times with ethyl acetate and the combined organic layers washed with brine, dried over MgSO4, filtrated and evaporated. Purification by Combi flash chromatography with a column of 24 g and a gradient cyclohexane: 0-100% ethyl acetate to give the title compound as a yellow solid (9.17 g, 26%).

Provenance & Evidence