Methyl iodide → 6-(tert-Butyl)-3-iodo-1-methyl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-tert-butyl-3-iodo-1H-indazole (820 mg, 2.73 mmol) in THF (8 ml) at 0° C. was added KOt-Bu (429 mg, 3.82 mmol). The reaction mixture was stirred at 0° C. for 30 min then added iodomethane (0.24 ml, 3.82 mmol). Stirred at 0° C. for 30 min then warmed to room temperature and stirred for 1.5 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organics were washed with brine then dried over MgSO4 and concentrated. The crude residue was purified by silica gel chromatography with 10% to 50% EtOAc/heptane to afford 592 mg (69%) of 6-tert-butyl-3-iodo-1-methyl-1H-indazole as a white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.37-7.43 (m, 1H), 7.31 (d, J=9.8 Hz, 2H), 4.10 (s, 3H), 1.41 (s, 9H). The minor 6-tert-butyl-3-iodo-2-methyl-1H-indazole regioisomer was also observed but not isolated.

Provenance & Evidence