2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (211 mg, 0.595 mmol), 5-amino-4-chloro-2-(3-hydroxypropyl)benzonitrile (125 mg, 0.595 mmol), palladium (II) acetate (40.1 mg, 0.178 mmol), DPPF (33.0 mg, 0.059 mmol), Xantphos (34.4 mg, 0.059 mmol), and cesium carbonate (388 mg, 1.189 mmol) were combined in a 20 dram vial and dioxane (6 mL) was added. The vial was evacuated and backfilled with N2 3×, then heated at 100° C. for 30 min. The reaction was cooled to room temperature and the reaction mixture was filtered through celite, rinsing with EtOAc. The solvent was removed in vacuo and the material was purified by ISCO Companion (0-3% MeOH/DCM; 12 g column). 2-((2-chloro-5-cyano-4-(3-hydroxypropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (253 mg) was obtained as a yellow glass.
