Chlorosuccinimide → 6-Bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

Participants

Reaction Steps

To a solution of 6-bromo-4-methoxypyrazolo[1,5-a]pyridine (1010 mg, 4.43 mmol) in acetonitrile (40 ml) was added N-chlorosuccinimide (1180 mg, 8.86 mmol). The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was partitioned between dichloromethane (100 ml) and 1N aqueous sodium hydroxide (100 ml). The organic layer was washed with brine (100 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to afford 6-bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.66 (s, 1H); 8.03 (s, 1H); 6.84 (s, 1H); 3.94 (s, 1H). LRMS (ESI) calculated for C8H6BrClN2O [M+H]+, 260.9; found 261.0.

Provenance & Evidence