A solution of 4-bromo-6-chloro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole (D10) (410 mg, 0.95 mmol) and KOH (212 mg, 3.8 mmol) in dioxane (10 mL) and water (10 mL) was sonicated under a flow of argon for 5 minutes after which the bis(1,1-dimethylethyl)[2′,4′,6′-tris(1-methylethyl)-2-biphenylyl]phosphane (24 mg, 0.057 mmol) and Pd2 dba3 (17 mg, 0.019 mmol) were added and it was heated to reflux for 2 hours. The mixture was then cooled to room temperature, diluted with EtOAc and water and the pH was adjusted to circa 7. The phases were separated, the aqueous re-extracted with EtOAc and the combined organics were finally dried over MgSO4. The crude material (450 mg) was purified by flash chromatography (Biotage SP4, 25+M silica column) with a gradient of EtOAc 0 to 50% in hexane to afford 60 mg of desired compound (D11).
