Methyl iodide → HCID 67299910, compound

To a solution of 5-bromo-2-hydroxymethyl-pyridine-1-oxide (6.43 g, 31.5 mmol) in THF (200 ml) was added sodium hydride (1.51 g, 63.1 mmol) at 0° C., and then the reaction mixture was stirred at ambient temperature for 1 h. After cooling to 0° C., methyl iodide (2.90 ml, 46.6 mmol) was added. The temperature was raised to ambient temperature and the reaction mixture was heated to 70° C. for 1 h. After cooling to 0° C. the reaction mixture was quenched with MeOH. The solvents were removed, and the crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 4.8 g (70%) of the title compound.

1. temperatureAfter cooling to 0° C.
2. temperatureThe temperature was raised to ambient temperature
3. temperaturethe reaction mixture was heated to 70° C. for 1 h
4. temperatureAfter cooling to 0° C. the reaction mixture
5. customwas quenched with MeOH
6. customThe solvents were removed
7. customthe crude product was purified by silica gel chromatography

ORD record

ord-dff00ff4b725402f848db5435530ede9

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703768B2