Methyl iodide → 3-iodo-5-isopropyl-1-methyl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-iodo-5-isopropyl-1H-indazole (0.75 g, crude) in 50 mL of THF at 0° C. was added t-BuOK (0.59 g, 5.2 mmol) in one portion. The mixture was stirred at 0° C. for 30 minutes. CH3I (1.1 g, 7.7 mmol) was added and the solution was stirred at room temperature overnight. The reaction was quenched with 30 mL of water and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL) and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated under reduced pressure to give crude 3-iodo-5-isopropyl-1-methyl-1H-indazole which contained some N-2 alkylation isomer (0.7 g) as oil. LCMS: (M+H)+=301.

Provenance & Evidence