To a solution of Dess Martin periodane (1.30 g, 3.05 mmol) in THF (5 mL) at 0° C. was added a solution of (6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)pyridin-3-yl)methanol (0.925 g, 2.55 mmol). The mixture was warmed to room temperature and stirred for 30 minutes, diluted with ether and hydrolyzed with 1N NaOH (40 mL). The mixture was extracted with ether, washed with brine, dried, and concentrated to afford 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinaldehyde (0.860 g, 93.5% yield) as a light yellow solid. 1H NMR (DMSO d6) δ 11.28 (bs, 1H), 10.40 (s, 1H), 8.75 (s, 1H), 8.09 (d, 1H), 7.98 (d, 1H), 7.92 (d, 1H), 7.55-7.68 (m, 3H), 7.49 (d, 1H), 6.62 (s, 1H), 6.26 (bs, 1H), 2.13 (s, 3H).
