Isopropyl iodide → 4-iodo-1-isopropyl-1H-indazole-6-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of 4-iodo-1H-indazole-6-carboxylic acid methyl ester (2.0 g, 6.62 mmol) in DMF (50 mL) was added Cs2CO3 (4.32 g, 13.24 mmol) followed by 2-iodopropane (0.5 mL, 7.94 mmol). The reaction mixture was stirred overnight at room temperature, then partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to provide 1.13 g (50%) of 4-iodo-1-isopropyl-1H-indazole-6-carboxylic acid methyl ester (0.73 g (32%) of the regioisomer 4-iodo-2-isopropyl-2H-indazole-6-carboxylic acid methyl ester was also recovered).

Provenance & Evidence