Bromine → HCID 86639841, compound

To a solution of 3-methoxy-2(1 h)-pyridone (1.00 g, 7.99 mmol, AstaTech, Inc) in DCM (26 mL) at 0° C. was slowly added bromine (0.819 mL, 15.98 mmol). After addition, the mixture was stirred at rt for 18 h. The mixture was then cooled to 0° C. and saturated aqueous NaHCO3 (4 mL) was slowly added. The mixture was then stirred at rt for 30 min. The organic layer was collected and the aqueous layer was extracted with EtOAc (1×20 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was then dissolved in MeOH (20 mL) and silica gel was added. The mixture was concentrated and dried in vacuo. The solid mixture was purified by silica gel flash column chromatography (solid loading, 0%-100% EtOAc/hexane) to give the title compound as a tan solid. MS (ESI, positive ion) m/z: 204,206 (M+H).

1. customat 0° C.
2. additionAfter addition
3. temperatureThe mixture was then cooled to 0° C.
4. stirringThe mixture was then stirred at rt for 30 min
5. customThe organic layer was collected
6. extractionthe aqueous layer was extracted with EtOAc (1×20 mL)
7. dry with materialThe combined organic layers were dried over MgSO4
8. concentrationconcentrated in vacuo
9. dissolutionThe residue was then dissolved in MeOH (20 mL)
10. additionsilica gel was added
11. concentrationThe mixture was concentrated
12. customdried in vacuo
13. customThe solid mixture was purified by silica gel flash column chromatography (solid loading, 0%-100% EtOAc/hexane)

ORD record

ord-8fd5cb8d89794dceb53726ecea9dab26

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096527B2