Methyl iodide → 6-Fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine

Participants

Reaction Steps

In a round-bottomed flask, 6-fluoro-2H-imidazo[1,5-a]pyridine-3-thione (158 mg, 0.94 mmol) was suspended in methanol (1 ml) and sodium methoxide (0.5 M in MeOH, 2.0 ml, 1.0 mmol) was added dropwise. The reaction was stirred at room temperature for 10 min then methyl iodide (0.07 ml, 1.12 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane then the organic layers were combined, dried over sodium sulfate, filtered and concentrated to afford 179 mg of 6-fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine as a brown oil which was used without further purification. 1H NMR (CDCl3, 400 MHz): δ (ppm) 7.98-8.05 (m, 1H), 7.58 (s, 1H), 7.45 (dd, J=9.3, 4.8 Hz, 1H), 6.73 (ddd, J=9.6, 7.6, 2.0 Hz, 1H), 2.56 (s, 3H).

Provenance & Evidence