Synthesis
General procedure for the synthesis of 2-pyridinylalkynyltrimethylsilanes from 2-bromopyridine and trimethylsilylethynes: 100 mL of diisopropylamine solution containing 2-bromopyridine (4.74 g, 0.030 mol), CuI (0.14 g, 0.74 mmol), and Pd(PPh3)2Cl2 (0.52 g, 0.74 mmol) was added to a solution containing 2-bromopyridine (4.74 g, 0.030 mol), CuI (0.14 g, 0.74 mmol), and Pd(PPh3)2Cl2 (0.52 g, 0.74 mmol), protected by nitrogen. trimethylsilylacetylene (3.0 g, 0.030 mol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified to give 5.0 g (95% yield) of 2-(trimethylsilyl)ethynylpyridine.
References
[1] Synthesis, 1983, # 4, p. 312 - 314
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727
[3] Phosphorus, Sulfur and Silicon and Related Elements, 2002, vol. 177, # 5, p. 1041 - 1045
[4] Patent: WO2006/93466, 2006, A1. Location in patent: Page/Page column 28
[5] Journal of Organometallic Chemistry, 2009, vol. 694, # 9-10, p. 1317 - 1324
