Dimethylformamide → 5-bromo-3-(methoxymethoxy)-1-(methoxymethyl)pyridin-2(1H)-one

To a suspension of 5-bromopyridine-2,3-diol (5.00 g, 26.3 mmol) in DMF (100 ml) at 0° C. was added sodium hydride (1.11 g, 26.3 mmol) portion-wise. The resulting mixture was allowed to stir for 30 minutes and then methoxymethyl chloride (2.00 ml, 26.3 mmol) was added. Upon warming to room temperature and stirring for 2 hours the reaction mixture was cooled to 0° C. and a further quantity of sodium hydride (1.11 g, 26.3 mmol) was added, followed after 20 minutes by the addition of more methoxymethyl chloride (2.00 ml, 26.3 mmol). The reaction mixture was then allowed to stir at room temperature for 48 hours and then poured slowly into saturated aqueous sodium carbonate solution. The resulting mixture was extracted with ethyl acetate and the organics were evaporated and purified by column chromatography (SiO2; 0-50% ethyl acetate in petrol) to yield 5-bromo-3-(methoxymethoxy)-1-(methoxymethyl)pyridin-2(1H)-one (3.8 g, 52%).

1. stirringstirring for 2 hours the reaction mixture
2. temperaturewas cooled to 0° C.
3. stirringto stir at room temperature for 48 hours
4. extractionThe resulting mixture was extracted with ethyl acetate
5. customthe organics were evaporated
6. custompurified by column chromatography (SiO2; 0-50% ethyl acetate in petrol)

ORD record

ord-8b4a2f9025544c12862a295eac6f872d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09180122B2