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

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).

1. stirringThe reaction mixture was stirred at room temperature for 2 h
2. concentrationthen concentrated
3. customThe residue was partitioned between dichloromethane and water
4. extractionThe aqueous layer was extracted with dichloromethane
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-22587c21dd7b492cae8ef59cc5220728

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2