Bromine → HCID 89815694, compound

Temperature

0 °C

Bromine (0.539 mL, 10.52 mmol) was added dropwise to a 0° C. mixture of 2-oxo-1,2-dihydro-1,7-naphthyridine-3-carboxylic acid (1.00 g, 5.26 mmol) in pyridine (25.0 mL). The mixture stirred at 0° C. for 20 minutes and then at room temperature for 18 hours. The reaction was then heated at 50° C. for 18 hours. The reaction mixture was then concentrated to afford a brown solid. This material was partitioned between DCM and saturated aqueous sodium thiosulfate solution. The aqueous phase was separated and extracted with DCM. The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford a brown solid. The resulting material was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% MeOH in DCM to afford 3-bromo-1,7-naphthyridin-2(1H)-one (0.562 g, 2.497 mmol, 47.5% yield) as a tan solid. m/z (ESI) 225.0, 227.0 (M+H)+.

1. waitat room temperature for 18 hours
2. temperatureThe reaction was then heated at 50° C. for 18 hours
3. concentrationThe reaction mixture was then concentrated
4. customto afford a brown solid
5. customThis material was partitioned between DCM and saturated aqueous sodium thiosulfate solution
6. customThe aqueous phase was separated
7. extractionextracted with DCM
8. washThe combined organic phases were washed with water and brine
9. dry with materialdried over anhydrous Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customto afford a brown solid
13. customThe resulting material was purified
14. washRediSep 40 g column, gradient elution with 0-10% MeOH in DCM

ORD record

ord-2a9731480a134160a1e8f61ca147a60a

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340549B2