Methyl iodide → HCID 71279836, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-iodo-1H-thieno[3,2-c]pyrazole (500 mg, 2.0 mmol) in THF (7 ml) at 0° C. was added KOt-Bu (314 mg, 2.8 mmol). The reaction mixture was stirred at 0° C. for 30 min then added iodomethane (0.17 ml, 2.8 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 20% to 50% EtOAc/heptane to afford 292 mg (55%) of 3-iodo-1-methyl-1H-thieno[3,2-c]pyrazole as a light brown viscous oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.41 (d, J=5.3 Hz, 1H), 6.97 (d, J=5.3 Hz, 1H), 4.05 (s, 3H). Also isolated 141 mg (27%) of 3-iodo-2-methyl-2H-thieno[3,2-c]pyrazole as an off-white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.36 (d, J=5.3 Hz, 1H), 7.16 (d, J=5.3 Hz, 1H), 4.13 (s, 3H).

Provenance & Evidence