An oven dried vial was charged with 6-bromo-4-chloro-1-methyl-1H-indazole (507 mg, 2.1 mmol), 5,5,5′,5′-tetramethyl-2,2′-bi(1,3,2-dioxaborinane) (649 mg, 1.9 mmol), oven dried KOAc (604 mg, 6.2 mmol), [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (54 mg, 0.066 mmol) and dioxane (10 mL), and purged with nitrogen for 20 min. The reaction was heated at 100° C. for 1 h. The mixture was filtered through a pad of Celite®, and the filter cake was rinsed with dioxane. The filtrate was concentrated under reduced pressure to afford the crude residue (530 mg). To a solution of this crude residue (370 mg) in degassed dioxane (2 mL) was added (R)-3-(6-chloro-2-methoxypyridin-3-yl)-3-methylpiperidin-2-one (300 mg, 1.2 mmol), an aqueous solution of sodium carbonate (2 M, 1.5 mL, 2.9 mmol) and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (54 mg, 0.066 mmol). The reaction mixture was degassed with nitrogen, and heated at 100° C. for 1 h. The reaction mixture was cooled to r.t., and anhydrous Na2SO4 was added. The mixture was filtered through a pad of Celite®, and the filter cake was rinsed with dioxane. The filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0-100% EtOAc in Heptane to 0-30% EtOH/DCM) to afford (R)-3-(6-(4-chloro-1-methyl-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylpiperidin-2-one (358 mg, 79%). 1H NMR (600 MHz, CDCl3) δ 1.68 (d, 1H), 1.74 (s, 3H), 1.88 (d, 1H), 1.97-2.07 (m, 1H), 2.39 (td, 1H), 3.37-3.47 (m, 1H), 3.50-3.60 (m, 1H), 4.12 (s, 3H), 4.15 (s, 3H), 5.81 (brs, 1H), 7.42 (d, 1H), 7.70 (d, 1H), 7.82 (s, 1H), 7.94 (s, 1H), 8.06 (s, 1H). MS (AP+)(M+H) 385.
