Potassium Carbonate → HCID 66778296, compound

1-(5-Fluoro-2-hydroxyphenyl)ethanone (4.0 g) was dissolved in acetonitrile (80 mL). To the reaction mixture were added potassium carbonate (4.8 g) and 2-bromo-1-cyclohexylethanone (7.3 g) synthesized in Example A51(1) at room temperature, and the mixture was stirred at room temperature for 8 hr. The reaction mixture was filtered through celite, rinsed with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (50 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (5.3 mL) was added to the solution, and the mixture was stirred with heating at 110° C. for 1 hr. After cooling to room temperature, the reaction mixture was quenched with 1N hydrochloric acid, and the mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the precipitated compound was recrystallized from diisopropyl ether-ethanol to give the title object compound (4.7 g, 76%) as a colorless solid.

1. customsynthesized in Example A51(1) at room temperature
2. filtrationThe reaction mixture was filtered through celite
3. washrinsed with ethyl acetate
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe residue was dissolved in N,N-dimethylformamide (50 mL)
6. addition1,8-diazabicyclo[5.4.0]undec-7-ene (5.3 mL) was added to the solution
7. stirringthe mixture was stirred
8. temperaturewith heating at 110° C. for 1 hr
9. temperatureAfter cooling to room temperature
10. customthe reaction mixture was quenched with 1N hydrochloric acid
11. extractionthe mixture was extracted with diethyl ether
12. concentrationThe extract was concentrated under reduced pressure
13. customthe precipitated compound was recrystallized from diisopropyl ether-ethanol

ORD record

ord-145f63047902424499c65ae7e0f086c9

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2