Pyridine → 4-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-6-methyl-1h-indazole

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Reaction Steps

The 4-bromo-6-methyl-1H-indazole (950 mg, 4.5 mmol), the {3-fluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid (2.2 g, 9 mmol), copper (II) acetate (1.22 g, 6.75 mmol) and pyridine (0.73 mL, 9 mmol) in DCM (80 mL) were stirred in the presence of molecular sieves (4 A, 2 g) in air. After 40 hours the mixture was filtered through a pad of celite and concentrated to afford 3.3 g of crude material. This was purified by flash chromatography (Biotage SP4, 40+M silica column) with a gradient of EtOAc 0 to 30% in hexane to afford 1.98 g of desired compound (D12) slightly impure but carried forward.

Provenance & Evidence