Potassium Carbonate → 3-Bromo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

To a stirred solution of 3-bromo-4-nitro-1H-indazole (Preparation B; 40 g, 165 mmol) in anhydrous DMF (320 mL) was added at ambient temperature potassium carbonate (45.7 g, 331 mmol). 2-(Chloromethyl)-6-methylpyridine hydrochloride (31 g, 174 mmol) was added in portions, and the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between water (800 mL) and methylene chloride (1000 mL). The phases were separated and the aqueous phase was extracted further with methylene chloride (200 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to give a brown solid. The crude product was triturated with ether (400 mL) and the solids were collected by filtration, washed with ether, and dried under vacuum to afford the desired product as brown solid (46 g).