2,6-Dibromo-1,5-naphthyridine → 2-Bromo-6-methoxy-1,5-naphthyridine

Temperature

0 °C

A 3-necked roundbottom flask was charged with a solution of 2,6-dibromo-1,5-naphthyridine (39 g, 135.42 mmol) in methanol (150 ml). The mixture was cooled to 0° C. and a solution of sodium methoxide (8.77 g, 162.41 mmol) in methanol (50 ml) was added dropwise. The resulting solution was allowed to react, with stirring, for three hours at 0° C. The reaction mixture was cooled to <0° C. and a solid precipitated. The mixture was filtered and the filtrated was quenched by the addition of 500 ml of ice water. The solids that formed were collected by filtration and them dissolved in ethyl acetate and dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography using 1:10 ethyl acetate:petroleum ether as eluant to afford the title compound.

1. customto react
2. temperatureThe reaction mixture was cooled to <0° C.
3. customa solid precipitated
4. filtrationThe mixture was filtered
5. customthe filtrated was quenched by the addition of 500 ml of ice water
6. customThe solids that formed
7. filtrationwere collected by filtration and them
8. dissolutiondissolved in ethyl acetate
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure
12. customThe resulting residue was purified by silica gel chromatography

ORD record

ord-a3677e2cb5e24d4d8f1bdd91baef800e

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344144B2