A solution of 4-bromo-2-iodo-1-methoxybenzene (Preparation 57, 350 mg, 1.12 mmol), 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 365 mg, 1.12 mmol) and aqueous caesium carbonate solution (1M, 2.23 mL, 2.23 mmol) in dioxane (18 mL) was degassed with nitrogen for 10 min, followed by addition of 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (46.0 mg, 0.0056 mmol). The resulting mixture was heated at 80° C. for 16 hours. After cooling to room temperature and concentration in vacuo, the crude residue was partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The organic layers were combined and washed with brine (25 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with heptanes/EtOAc (70:30), to afford the title compound as off-white solid in 45% yield, 150 mg.
