To a solution of 4-(benzyloxy)-1-(1H-indazol-5-yl)pyridin-2(1H)-one (0.362 g, 1.14 mmol) in DMSO (1.5 mL) was added 4-(2-chloroethyl)morpholine (0.466 g, 2.50 mmol) and Cs2CO3 (1.85 g, 5.67 mmol). After stirring at ambient temperature for 5.5 h, the reaction mixture was diluted with H2O (10 mL) and extracted with EtOAc (3×40 mL). The organics were washed with brine (2×25 mL), dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) followed by preparative HPLC (Phenomenex Luna C18 (2), 250.0×50.0 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) yielded the title compound (37.3 mg, 7%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 8.02 (d, J=1.0 Hz, 1H), 7.66 (d, J=1.5 Hz, 1H), 7.50 (d, J=9.0 Hz, 1H), 7.43-7.38 (m, 6H), 7.29 (d, J=7.5 Hz, 1H), 6.09-6.06 (m, 2H), 5.06 (s, 2H), 4.53 (t, J=7.0 Hz, 2H), 3.68 (t, J=4.5 Hz, 4H), 2.88 (t, J=6.5 Hz, 2H) 2.52 (t, J=4.5 Hz, 4H); ESI MS m/z 431 [M+H]+; HPLC (Method A) 98.9% (AUC), tR=14.0 min.
