The general procedure for the synthesis of 5-(3-fluorophenyl)-2-methylpyridine from 3-fluorophenylboronic acid and 6-methyl-3-pyridinol trifluoromethanesulfonate was as follows: 6-methyl-3-pyridinol trifluoromethanesulfonate (6.2 g, 25.7 mmol), 3-fluorophenylboronic acid (4.3 g, 30.7 mmol), potassium carbonate ( 10.7 g, 77.4 mmol) and tetrakis(triphenylphosphine)palladium (297 mg, 0.26 mmol). A solvent mixture of toluene/ethanol/water (4:2:1, 60 mL, v/v) was subsequently added. The reaction mixture was heated to 120 °C and the reaction was stirred at this temperature for 22 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with the addition of water. The mixture was extracted with ethyl acetate and the organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10:1) to afford the target product 5-(3-fluorophenyl)-2-methylpyridine (4.3 g, 97% yield). The structure of the product was confirmed by 1H-NMR (300 MHz, CDCl3): δ 2.62 (s, 3H), 7.04-7.47 (m, 5H), 7.76 (dd, J = 8.1 Hz, 2.4 Hz, 1H), 8.72 (d, J = 2.1 Hz, 1H).
