To the solution of 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-N-cyclopropyl-1-phenyl-1H-pyrazole-3-carboxamide in dioxane (Preparation 10, 0.63 mmol, 15 mL) was added 2-bromo-3-fluoropyridine (58 mg, 0.33 mmol), Na2CO3 (46.6 mg, 0.44 mmol) in water (1 mL) and Pd(dppf)Cl2 (9 mg, 0.01 mmol). The reaction was degassed with nitrogen for 30 minutes and heated to 110° C. for 17 hours. The reaction was cooled and concentrated in vacuo. The residue was eluted through a small plug of silica with EtOAc followed by reverse phase column chromatography eluting with 3-60% MeCN (containing 0.1% NH4OH) in water (containing 0.1% NH4OH) to afford the title compound (20 mg, 19%).
