tert-Butyl 4-(3-amino-4-carbamoyl-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate (Intermediate 35-1) (500 mg, 1.44 mmol), potassium acetate (211 mg, 2.15 mmol), 1,3-dibromobenzene (0.69 mL, 5.74 mmol) and 2-propanol (7.2 mL) were combined in a vial and purged with a stream of N2 gas for 10 minutes. Pd2(dba)3 (52 mg, 0.060 mmol) and 2-di-t-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-tri-i-propylbiphenyl (103 mg, 0.220 mmol) were then added. The reaction vessel was capped and the reaction mixture was heated to 85° C. and allowed to stir for 16 hours. The mixture was then cooled to ambient temperature, filtered through celite, eluting with EtOAc. The filtrate was concentrated in vacuo and the residue was purified by MPLC on silica gel (using a gradient elution of 0-10% MeOH/DCM) to afford the title compound, Example #12-1.
