Water → 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

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Reaction Steps

To a solution of 5-nitroindazole (2 g, 12.3 mmol) in DMF (20 mL) was added K2CO3 (5.1 g, 36.8 mmol) and 2-(bromomethyl)-pyridine (2.2 g, 13.5 mmol). The resulting mixture was stirred at RT for 3.5 days, then poured into 100 mL of water. The resulting slurry was filtered, rinsed once with water and dried in vacuo giving a solid. The crude material was purified by chromatography (SiO2, elution with 3:1 EtOAc-hexanes followed by EtOAc followed by 7:1 CH2C2—MeOH) giving 5-nitro-1-pyridin-2-ylmethyl-1H-indazole and 5-nitro-2-pyridin-2-ylmethyl-1H-indazole.

Provenance & Evidence