In a flask containing 2-(3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoroethyl)azetidin-3-yl)acetonitrile (0.015 g, 0.038 mmol), 1-ethyl-1H-pyrazol-4-ylboronic acid (0.0080 g, 0.057 mmol), and K3PO4 (0.057 mL, 0.11 mmol) was added 1 mL of dioxane and argon was bubbled through for 10 minutes before dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0036 g, 0.0076 mmol) and tris(dibenzylideneacetone)dipalladium (0.0035 g, 0.0038 mmol) were added and the reaction was then sealed and heated to 80° C. for 6 hours. The reaction mixture was loaded directly onto a silica gel column and eluted with EtOAc containing 0.5% NH4OH to afford the title compound (0.015 g, 0.031 mmol, 83% yield). MS (apci) m/z=456.2 (M+H).
