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0 °C

Sodium hydride (85 mg, 60%, 2.12 mmol) was added to an ice-cooled solution of 6-iodo-1H-indazole (249.5 mg, 1.02 mmol) in DMF (2.5 mL). After stirring this mixture for 1 h at 0° C., 2-iodopropane (0.32 mL, 3.2 mmol) was added and the mixture stirred at 100° C. for 16 h. After the reaction mixture was partitioned between water and ethyl acetate, the organic layer was washed sequentially with water and brine, dried over sodium sulfate and the solvent removed in vacuo. Flash chromatography (silica gel, 5-20% ethyl acetate in hexane) yielded two products, the less polar 1-substituted-1H-indazole (105 mg) and the more polar 2-substituted indazolium (107.7 mg).

1. stirringthe mixture stirred at 100° C. for 16 h
2. customAfter the reaction mixture was partitioned between water and ethyl acetate
3. washthe organic layer was washed sequentially with water and brine
4. dry with materialdried over sodium sulfate
5. customthe solvent removed in vacuo
6. customFlash chromatography (silica gel, 5-20% ethyl acetate in hexane) yielded two products