2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (218 mg, 0.614 mmol), 3-amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrile (138 mg, 0.614 mmol), palladium(II) acetate (41.4 mg, 0.184 mmol), DPPF (34.1 mg, 0.061 mmol), Xantphos (35.6 mg, 0.061 mmol), and cesium carbonate (400 mg, 1.229 mmol) were combined in a 50 ml flask and dioxane (6 mL) was added. The flask was evacuated and backfilled with N2 3×, then heated at 100° C. for 1 h. The reaction was cooled to room temperature and filtered through celite, rinsing with EtOAc. The solvent was removed in vacuo. The material was purified by flash column chromatography (0%-50% EtOAc/DCM; 80 g column). 2-((2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (179 mg) was obtained as an orange glass.
