O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (150 mg, 0.413 mmol), palladium(II)acetate (9.2 mg, 0.041 mmol), 1,1′-bis(diphenylphosphino)ferrocene (45 mg, 0.083), lithium chloride (105 mg, 2.48 mmol), and 15 mL of 1,4-dioxane were combined and stirred for 5 minutes. 2-Tributylstannylpyridine (197 μL, 0.537 mmol) was added and the mixture was heated to reflux (about 105° C.) and stirred for about 18 hours. 50 mL of 8M aqueous potassium fluoride solution was added and the solution was extracted with 3:1 chloroform:isopropanol and brine and concentrated in vacuo. The residue was purified by silica gel flash chromatography (0-20% methanol:dichloromethane) to give 31.1 mg of the title compound. (26%). MS(FD) m/e 293.1 (M+).
