N-Iodosuccinimide → HCID 58404704, compound

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.

1. stirringthe mixture was stirred for 30 minutes, at which time LCMS
2. stirringthe mixture was stirred for 30 minutes, at which time LCMS
3. stirringthe mixture was stirred for 30 minutes, at which time LCMS
4. washwashed with 1N aqueous sodium hydroxide and brine
5. dry with materialthen dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

ORD record

ord-122d0dac88884fdf93527abd31a10f84

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2