To a stirred solution of 2-fluoro-6-(p-methoxybenzylamino)-4-pyridine-methanol (790 mg, 2.84 mmol) in chloroform (28 ml) at 0° C. (ice bat), was added triethylamine (597 μl, 4.26 mmol) followed by methanesulfonyl chloride (256 μl, 3.41 mmol). After stirring for 1.5 hr., the mixture was diluted with dichloromethane, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo and mixed with compound 8 (945 mg, 2.84 mmol), anhydrous powdered potassium carbonate (392 mg, 2.84 mmol), and lithium iodide (381 mg, 2.84 mmol). Anhydrous DMF (15 ml) was then added into the mixture and stirred for overnight at room temperature. The mixture was evaporated in vacuo. The residue was dissolved in methanol-dichloromethane (1:9), filtered through a celite pad, and the pad was washed with dichloromethane. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:2)) to afford 963 mg (57%) of a white foam. 1H NMR (200 MHz, CDCl3) δ 1.11 (6H, d, J=7.0 Hz), 2.30 (3H, s), 2.72 (1H, m), 3.79 (3H, s), 3.93-4.06 (4H, m), 4.30 (2H, d, J=5.4 Hz), 4.67 (2H, s), 5.04 (1H, t, J=5.4 Hz), 5.67 (1H, s), 5.96 (1H, s), 6.36 (1H, s), 6.57 (1H, s), 6.79 (1H, s), 6.85 (2H, d, J=8.4 Hz), 7.01 (1H, s), 7.22 (2H, d, J=8.4 Hz), 9.01 (1H, s).
