Water → HCID 70984374, Verbindung

Temperatur

80 °C

To a mixture of 6-fluoro-2-methylquinolin-8-ol (0.15 g, 0.85 mmol) and potassium carbonate (4.2 g, 30 mmol) in acetonitrile (3.4 mL, 0.85 mmol) and water (3.4 mL, 0.85 mmol) was added 2-chloro-2,2-difluoroacetophenone (0.62 mL, 4.2 mmol). The vessel was sealed and the mixture was heated at 80° C. for 4 hours. The cooled reaction mixture was extracted with diethyl ether (2×30 mL), and the combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure at ambient temperature The resulting residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water). Aqueous fractions containing the product were combined and extracted with diethyl ether (2×100 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure at ambient temperature providing the title compound. Presence of water was noted and the material taken on as is assuming theoretical yield obtained (0.19 g, 100%).

1. customThe vessel was sealed
2. customThe cooled reaction mixture
3. extractionwas extracted with diethyl ether (2×30 mL)
4. dry with materialthe combined organic extracts were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure at ambient temperature The resulting residue
7. customwas purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water)
8. additionAqueous fractions containing the product
9. extractionextracted with diethyl ether (2×100 mL)
10. dry with materialThe combined organic extracts were dried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure at ambient temperature

ORD-Eintrag

ord-75c94b7ae1fc4b6fba7882526e3a2fab

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889704B2