Reaction Steps
To a suspension of 8-(3-chlorophenyl)-1,6-naphthyridin-5-one (128 mg, 0.5 mmoles), thiophenemethanol (0.08 ml, 0.6 mmoles), and triphenylphosphine (197 mg, 0.75 mmoles) was added dropwise diisopropylazodicarboxylate (0.15 ml, 0.75 mmoles) under an atmosphere of nitrogen at 21° C. The reaction mixture was stirred overnight and concentrated under vacuum to give an oil. The oil was chromatographed with silica gel (eluting with 1:4 ethyl acetate/hexane) to give (after crystallization from methanol) 98 mg (56% yield) of the desired 6-(2-thienylmethyl)-8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid: mp 141.5°-145.0° C; 1H NMR (CDCl3, 300 MHz) δ5.41 (s, 2H), 6.97-7.56 (m, 9H), 8.78 (dd, 1H, J=8.1, 1.9), 8.93 (dd, 1H, J=4.5, 1.9); 13C NMR (75 MHz, CDCl3) δ161.56, 154.34, 151.68, 137.91, 136.93, 136.79, 134.14, 133.70, 130.04, 129.54, 128.26, 127.81, 127.77, 127.09, 126.65, 122.13, 121.91, 120.05, 46.85; IR (KBr) vmax 1643, 1612, 1591, 1564, 1552, 1483, 1441, 1429, 1415, 1377, 1358, 1302, 1207, 1174, 792, 763, 734, 715, 696, 601 cm-1 ; mass spectrum (EI), m/e 352. Anal. (C19H13ClN2OS) Calcd.: C, 64.68; H, 3.71; N, 7.94. Found: C, 64.45; H, 3.69; N, 8.00.
