Triethylamine → 5-Bromo-2-[2-(trimethylsilyl)ethynyl]pyridine

Participants

Reaction Conditions

Reaction Steps

1.15 g (1.63 mmol) of tetrakistriphenylphosphine palladium, 0.311 g (1.63 mmol) of copper (1) iodide, and 50 mL of triethylamine are added to a solution of 20 g (81.89 mmol) of 2,5-dibromopyridine in 250 mL of absolute THF under an argon atmosphere. At 17° C., a solution of 13 mL (90.14 mmol) of trimethylsilylacetylene in 20 mL of THF is immediately added dropwise to this reaction mixture. After ten minutes, the cooling is removed. After 20 minutes, the temperature is 30° C. The mixture is then cooled to 20° C. and briefly stirred. The reaction mixture is evaporated down, the residue is taken up in ethyl acetate and extracted twice with sodium hydrogen carbonate solution. The combined organic phases are dried over magnesium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether). Yield: 20.4 g (98% of theory); C10H12BrNSi (M=254.20); calc.: molecular ion peak (M+H)+: 254/256; found: molecular ion peak (M+H)+: 254/256; Rf value: 0.72 (silica gel, petroleum ether).

Provenance & Evidence