Isopropyl iodide → HCID 12991242, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence