To a microwave vial was added tert-butyl 4-(3-amino-4-carbamoyl-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate (Intermediate 35-1) (5.0 g, 14 mmol), 4-bromo-2-fluoropyridine (2.5 g, 14 mmol), K3PO4 (6.1 g, 29 mmol), and dioxane (72 mL). The mixture was degassed with bubbling argon for 5 minutes. Pd2(dba)3 (0.7 g, 0.7 mmol) and X-Phos (1.0 g, 2.2 mmol) were then added, and the vial was sealed and heated to 95° C. for 5 hours. The mixture was then cooled to ambient temperature, diluted with EtOAc, filtered through celite, and eluted with EtOAc. The filtrate was concentrated in vacuo, and the resulting yellow oil was purified by MPLC on silica gel (using a gradient elution of 50-100% EtOAc/hexanes) to afford the title compound, Example #9-1.
