Using the method of Example 3, Step B, 4-methylthiazol-2-amine (25.2 mL, 10.1 mmol), ethyl 6-chloro-4-(naphthalen-1-yloxy)nicotinate (3.63 g, 11.1 mmol), potassium phosphate (2.35 g, 11.1 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.231 g, 0.252 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.160 g, 0.277 mmol) were reacted in toluene (25 mL) and water (8 mL) to afford ethyl 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinate (3.30 g, 80.0% yield) as yellow solid. 1H NMR (CDCl3) δ 9.90 (bs, 1H), 8.91 (s, 1H), 7.97 (d, 1H), 7.91 (d, 1H), 7.77 (d, 1H), 7.53 (m, 1H), 7.47 (m, 1H), 7.43 (m, 1H), 7.14 (d, 1H), 6.18 (s, 1H), 5.90 (s, 1H), 4.37 (quart, 2H), 1.76 (s, 3H), 1.33 (t, 3H); Mass spectrum (apci) m/z=406 (100) (M+H).
