Pd Catalyst 1 (12.6 mg, 0.045 mmol, calculated based on the molar concentration of Pd) and 3-chloro-4-methylpyridine (0.2 mmol) were added to a Schlenk tube equipped with a magnetic stir bar. Anhydrous toluene (2.0 mL) and phenylmagnesium bromide (0.3 mmol, 1.5 equiv) were added sequentially under nitrogen protection. The reaction mixture was heated to 140 °C and the reaction was stirred at this temperature until complete consumption of 3-chloro-4-methylpyridine was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the reaction mixture was purified by silica gel column chromatography to afford the target product 3-phenyl-4-methylpyridine.
