A suspension of triphenylphosphine (0.033 g, 0.125 mmol), K2CO3 (0.118 g, 0.856 mmol), Pd(OAc)2 (0.007 g, 0.031 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole (0.089 g, 0.428 mmol) and 5-((2-chloropyridin-4-yl)oxy)-6-(trifluoromethyl)pyridin-2-amine (0.062 g, 0.214 mmol) in dioxane (6 mL) and water (1.5 mL) was sparged with Ar and heated at 85° C. overnight. The mixture was cooled to RT, treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated and purified via silica gel chromatography (MeOH/EtOAc) to afford 5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-(trifluoromethyl)pyridin-2-amine (55 mg, 77%). MS (ESI) m/z: 336.1 (M+H+).
