N-(4-(5-Iodo-2-methoxypyrimidin-4-yloxy)phenyl)-5-methylpyridin-2-amine (0.061 g, 0.14 mmol), 2-fluoropyridine-4-boronic acid (0.030 g, 0.21 mmol), and tetrakis(triphenylphosphine)palladium (0.016 g, 0.014 mmol) were mixed in dioxane (0.5 mL) under an argon atmosphere. Sodium carbonate (0.21 mL, 0.42 mmol, 2.0 M in water) was added via syringe, and the reaction mixture was stirred at 80° C. for 20 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was separated, washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to give N-(4-(5-(2-fluoropyridin-4-yl)-2-methoxypyrimidin-4-yloxy)phenyl)-5-methylpyridin-2-amine. MS (ESI, pos. ion) m/z: 404.2 (M+1). IC50 (uM) 0.016.
