To a stirred solution of 3-(4-hydroxyphenyl)-4-(pyridin-4-yl)furan-2(5H)-one (700 mg, 2.76 mmol) in DMF (10 mL) was added K2CO3 (763.6 mg, 5.5 mmol) followed by 2-(chloromethyl)quinoline (711 mg, 3.32 mmol). The reaction mixture was then heated at 80° C. for 2 h, quenched with cold water, and extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl) furan-2(5H)-one (190 mg, 19%) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 8.61 (d, J=7.7 Hz, 2H), 8.42 (d, J=7.1 Hz, 1H), 8.04-7.96 (m, 2H), 7.81-7.76 (m, 1H), 7.65 (d, J=7.4 Hz, 1H), 7.60-7.54 (m, 1H), 7.44-7.36 (m, 4H), 7.11 (d, J=7.2 Hz, 2H), 5.40 (s, 2H), 5.34 (s, 2H). MS: M+H: m/z=395.1 and HPLC: 95%, (Condition-H).
