Potassium Carbonate → 3-(1-cyano-1-methylethyl)-N-{4-ethyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Temperature

80 °C

To a solution of 2-chloro-5-nitropyridine (1.07 g, 6.81 mmol) and 3-(1-cyano-1-methylethyl)-N-(4-ethyl-3-hydroxyphenyl)benzamide (2.0 g, 6.48 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (1.34 g, 9.72 mmol), and the mixture was stirred at 80° C. for 12 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 mL), washed with water (150 mL), 5% aqueous sodium hydrogen carbonate solution (150 mL) and saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70). The obtained solution was concentrated under reduced pressure to give the title compound (3.3 g, quantitative) as a yellow amorphous substance.

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationthe insoluble material was filtered off
3. concentrationthe filtrate was concentrated under reduced pressure
4. additionThe obtained residue was diluted with ethyl acetate (200 mL)
5. washwashed with water (150 mL), 5% aqueous sodium hydrogen carbonate solution (150 mL) and saturated brine (150 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70)
10. concentrationThe obtained solution was concentrated under reduced pressure

ORD record

ord-e175a5698015498d85e62e65f602ef7e

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2