To a mixture of cesium carbonate (0.559 g, 1.72 mmol), 4-(pyridin-2-ylamino)phenol (0.320 g, 1.72 mmol), and 4-(2-fluoropyridin-3-yl)-1-methylpyrrolidin-2-one (0.110 g, 0.566 mmol) was added NMP (2 mL). The reaction mixture was degassed and heated to 100° C. for 2 h. The reaction mixture was diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (4×) and the combined organic extracts were washed with 1 M NaOH (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (30% to 100% EtOAc (10% MeOH) in hexanes) gave 1-methyl-4-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)pyrrolidin-2-one as a white solid and a 1:1 mixture of enantiomers. MS (ESI, pos. ion) m/z: 361.1 (M+1). IC50 (uM) 0.01406.
