Methyl iodide → 6-Bromo-1-methyl-1H-indazole-4-carbonitrile

Tetrahydrofuran (27 ml) was added to a flask containing sodium hydride (0.275 g, 6.89 mmol) and the mixture was stirred for 10 minutes at 0° C. 6-Bromo-1H-indazole-4-carbonitrile (1.39 g, 6.26 mmol) was added portionwise and the mixture was stirred for 10 mins until no further effervescence was seen. Iodomethane (0.431 ml, 6.89 mmol) was added and the mixture stirred at 0° C. for 1 h. The ice bath was removed and the flask was placed in a water bath at room temperature. The reaction remained stirring for 19 h and the mixture was then evaporated in vacuo. The residual solid purified by silica (100 g) cartridge using a gradient of ethyl acetate and cyclohexane to give the title compound as a white solid (370 mg).

1. stirringthe mixture was stirred for 10 mins until no further effervescence
2. stirringthe mixture stirred at 0° C. for 1 h
3. customThe ice bath was removed
4. customthe flask was placed in a water bath at room temperature
5. stirringThe reaction remained stirring for 19 h
6. customthe mixture was then evaporated in vacuo
7. customThe residual solid purified by silica (100 g) cartridge

ORD record

ord-54dacce16bd446f2966720af431031d6

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524751B2