Water → Methyl 5-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate

Temperature

65 °C

To a solution of methyl 6-oxo-1,6-dihydro-3-pyridinecarboxylate (2.00 g, 13.06 mmol, Bionet Research) in MeCN (40 mL) was added SelectFluor® (4.63 g, 13.06 mmol, Aldrich). The resulting mixture was then heated at 65° C. for 18 h. Then, the mixture was cooled to rt and water (20 mL) was added. The solvent, (MeCN) was removed and the remaining aqueous solution was extracted with EtOAc (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in MeOH (100 mL) and silica gel was added. The mixture was concentrated and dried in vacuo. Purification by silica gel flash column chromatography (0%-100% EtOAc/hexane) gave the title compound as a white solid. MS (ESI, positive ion) m/z: 172 (M+H).

1. temperatureThen, the mixture was cooled to rt
2. customThe solvent, (MeCN) was removed
3. extractionthe remaining aqueous solution was extracted with EtOAc (2×20 mL)
4. dry with materialThe combined organic extracts were dried (MgSO4)
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in MeOH (100 mL)
7. additionsilica gel was added
8. concentrationThe mixture was concentrated
9. customdried in vacuo
10. customPurification by silica gel flash column chromatography (0%-100% EtOAc/hexane)

ORD record

ord-56641ccb027e4af38e3dba85f353068d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096527B2