Reacción #91533

Ecuación de reacción

sodium bicarbonate

4-((6-(2-(2,4-Difluorophenyl)-1,1-difluoro-2oxoethyl)pyridin-3-yl)oxy)benzonitrile

trimethylsulfoxonium iodide

potassium tert-butoxide

→

title compound

Rendimiento 44.2%

4-((6-((2-(2,4-difluorophenyl)oxiran-2-yl)difluoromethyl)pyridin-3-yl)oxy)benzonitrile

Rendimiento 44.2%

Disolventes

Brine

THF

THF DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to 0° C
2. 2
   Temperaturato maintain the temperature below 5° C
3. 3
   TemperaturaThe reaction mixture was maintained at 0° C. for 30 min
4. 4
   Otroto quench
5. 5
   Otrothe reaction
6. 6
   Extracciónthe mixture was extracted with Et2O
7. 7
   workup.ADDITIONThe combined organic phases were diluted with hexanes
8. 8
   Lavadowashed with brine and water
9. 9
   Secadodried (Na2SO4)
10. 10
    Concentraciónconcentrated

Procedimiento

To a magnetically stirred solution of trimethylsulfoxonium iodide (6.4 g, 29.42 mmol) in dry THF/DMSO (10:6) was added potassium tert-butoxide (3.302 g, 29.42 mmol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 1 h and then cooled to 0° C. 4-((6-(2-(2,4-Difluorophenyl)-1,1-difluoro-2oxoethyl)pyridin-3-yl)oxy)benzonitrile (8.737 g, 22.63 mmol) in THF (40 mL) was added slowly to maintain the temperature below 5° C. The reaction mixture was maintained at 0° C. for 30 min and saturated sodium bicarbonate was added to quench the reaction. Brine was added and the mixture was extracted with Et2O. The combined organic phases were diluted with hexanes and washed with brine and water, dried (Na2SO4) and concentrated to give the title compound as an amber oil (4 g, 44%): 1H NMR (300 MHz, CDCl3) δ 8.46 (d, J=2.7 Hz, 1H), 7.73-7.62 (m, 2H), 7.52 (dd, J=8.6, 0.6 Hz, 1H), 7.48-7.35 (m, 2H), 7.13-7.02 (m, 2H), 6.92-6.80 (m, 1H), 6.75 (ddd, J=10.0, 8.9, 2.5 Hz, 1H), 3.46 (d, J=5.1 Hz, 1H), 3.03-2.96 (m, 1H); ESIMS m/z 401 ([M+H]+).

Fuente