N-Hydroxysuccinimide → 5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide

To a suspension of 5-bromonicotinic acid (5.0 g) and N-hydroxysuccinimide (4.27 g) in acetonitrile (60 ml) was added 1-ethyl-3—(3′-dimethylaminopropyl)carbodiimide hydrochloride (7.12 g) at room temperature, and the mixture was stirred for 30 minutes. To the reaction mixture were added N,O-dimethyl-hydroxylamine hydrochloride (2.66 g) and triethylamine (10 ml), and the mixture was stirred for 64 hours and concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=2:1) to give N-methyl-N-methoxy-5-bromopyridine-3-carboxamide (3.71 g) as pale yellow oil.

1. stirringthe mixture was stirred for 64 hours
2. concentrationconcentrated under reduced pressure
3. additionTo the residue was added water
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with saturated sodium chloride solution
6. dry with materialdried with magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was separated
9. custompurified with column chromatography (ethyl acetate/hexane=2:1)

ORD record

ord-d6b6a946c2074e3889a5909155d89cd3

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06413947B1