To a stirred solution of 2-(methylamino)ethanol (672 mg, 10 eq) in 20 mL anhydrous THF was added NaH (373 mg, 8.0 eq) at 0° C. The mixture was stirred at rt for 1 h, then to the mixture was added (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (300 mg, 1 eq, made from example 1). The reaction was heated at reflux for 16 h, cooled, quenched with sat. NH4Cl, and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (200 mg, 60% yield). 1H NMR (400 MHz, CDCl3) δ 7.59 (s, 1H), 7.18-7.20 (m, 2H), 7.08-7.16 (m, 3H), 7.01-7.06 (m, 3H), 6.77 (d, J=8.4 Hz, 1H), 6.28 (d, J=8.4 Hz, 1H), 4.28 (t, J=5.2 Hz, 2H), 2.93 (t, J=5.2 Hz, 2H), 2.46-2.55 (m, 5H), 0.92 (t, J=7.6 Hz, 3H); m/z=375 [M+1]+.
