A vial was charged with 7-bromo-4-(5-chloropyridin-3-yl)-2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (40 mg, 0.07 mmol), trimethylboroxine (10 μL, 0.07 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5 mg, 0.007 mmol), K3PO4 (37.2 mg, 0.175 mmol), dioxane (0.8 mL), and water (0.2 mL). The mixture was sparged with N2, the vial was sealed, and the reaction was heated at 100° C. for 90 minutes. The reaction was then cooled to room temperature, diluted with EtOAc (40 mL), and washed with water (10 mL) and brine (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified on a silica gel column with 0 to 100% EtOAc/hexanes to afford 4-(5-chloropyridin-3-yl)-2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-7-methyl-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd for C28H33ClN6O [M+H]+=505. found=505.
