N-Iodosuccinimide → HCID 58404704, compound

Participants

Reaction Steps

6-bromo-4-methoxypyrazolo[1,5-a]pyridine (50.0 mg, 0.220 mmol) was dissolved in acetonitrile (2 ml). N-iodosuccinimide (49.5 mg, 0.220 mmol) was added and the mixture was stirred for 1 h, at which time LCMS indicated about 60% conversion. Additional N-iodosuccinimide (9.9 mg, 0.044 mmol) was added and the mixture was stirred for 30 minutes, at which time LCMS indicated about 80% conversion. Additional N-iodosuccinimide (9.9 mg, 0.044 mmol) was added and the mixture was stirred for 30 minutes, at which time LCMS indicated about 80% conversion. Additional N-iodosuccinimide (14.9 mg, 0.066 mmol) was added and the mixture was stirred for 30 minutes, at which time LCMS indicated complete conversion. The reaction mixture was diluted in ethyl acetate, washed with 1N aqueous sodium hydroxide and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to give 6-bromo-3-iodo-4-methoxypyrazolo[1,5-a]pyridine as a colorless solid (faster eluting), along with recovered starting material 6-bromo-4-methoxypyrazolo[1,5-a]pyridine (slower eluting). 1H NMR (600 MHz, CDCl3) δ 8.25 (d, 1H); 7.80 (s, 1H); 6.47 (s, 1H); 3.93 (s, 3H). LRMS (ESI) calculated for C8H779BrIN2O [M+H]+, 352.9; found 352.8.

Provenance & Evidence