Sodium Bicarbonate → 7-Fluoro-2-methoxy-1,5-naphthyridine

8-Bromo-7-fluoro-2-(methoxy)-1,5-naphthyridine (for a synthesis see WO2004058144, Example 53(g)) (5.040 g, 19.61 mmol) was stirred in MeOH (200 ml) with sodium hydrogen carbonate (3.29 g, 39.22 mmol) and 10% palladium on carbon (2.5 g), and the resulting suspension was hydrogenated at 1 atmosphere of hydrogen pressure under for 4 h. The mixture was filtered with suction through celite and the solids were washed with MeOH (500 ml). The combined filtrate plus washings were concentrated to about 50 ml under reduced pressure and then treated with water (200 ml) and DCM (300 ml). The aqueous phase was separated and extracted twice more with DCM (300 ml). The combined organic phases were separated, dried over anhydrous magnesium sulphate, filtered and evaporated to give the desired compound as an off-white solid (3.044 g, 87%).

1. filtrationThe mixture was filtered with suction through celite
2. washthe solids were washed with MeOH (500 ml)
3. concentrationThe combined filtrate plus washings were concentrated to about 50 ml under reduced pressure
4. additiontreated with water (200 ml) and DCM (300 ml)
5. customThe aqueous phase was separated
6. extractionextracted twice more with DCM (300 ml)
7. customThe combined organic phases were separated
8. dry with materialdried over anhydrous magnesium sulphate
9. filtrationfiltered
10. customevaporated

ORD record

ord-0da16db5eb034e5b957f54a901bcd029

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071592B2