A suspension of 3-bromo-5-nitro-1-trityl-1H-indazole 1 (6 g, 12.41 mmol), 4-fluoro-3-hydroxymethylphenylboronic acid 10AV (2 g, 12.87 mmol), Pd(dppf)Cl2 (800 mg, 0.98 mmol) and K3PO4 (6 g, 28.30 mmol) in 124 mL of dioxane/H2O (25:6) was heated to 80° C. for overnight. After removal of most of the solvent, the black residue was diluted with EtOAc (250 mL) and H2O (60 mL). The resulting mixture was filtered through a pad of Celite. Additional 150 mL of EtOAc was used to wash the Celite cake. The filtrates were combined. The aqueous layer was separated and the organic layer was washed with brine, dried (MgSO4) and concentrated to give crude 3-(4-fluoro-3-hydroxymethylphenyl)-5-nitro-1-trityl-1H-indazole 11AV (8.2 g) as a greenish yellow solid.
