3-(1,1,1-Tributylstannyl)pyridine

626-55-1

1461-22-9

59020-10-9

In a two-necked round-bottomed flask 0.5 mL (5.19 mmol) of 3-bromopyridine was dissolved in 25 mL of anhydrous ether and the reaction system was cooled to -78 °C. 3.89 mL (6.23 mmol) of n-butyllithium (1.6 M hexane solution) was slowly added dropwise and the reaction was stirred for 3 hours keeping the temperature at -78 °C. Subsequently, 1.55 mL (5.71 mmol) of tributyltin chloride was added and stirring was continued at -78°C for 30 minutes, then gradually warmed to room temperature and stirred for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ether. The organic layer was separated, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. Purification by column chromatography (eluent: hexane/ethyl acetate=9:1, v/v) afforded 1.58 g of the target product 3-(1,1,1-tributylmethylstannyl)pyridine as a clear oil (yield: 83%).