Reacción #61006

Ecuación de reacción

1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

imidazole

cesium carbonate

1,10-phenanthroline

→

title compound

Rendimiento 41.9%

1-{3-Fluoro-4-[4-(5-imidazol-1-yl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone

Rendimiento 41.9%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Otroquenched with water/ethyl acetate
3. 3
   ExtracciónThe aqueous layer was extracted twice with ethylacetate
4. 4
   Secadodried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent was removed in vacuo
7. 7
   OtroThe crude oil was chromatographed over silicagel

Procedimiento

In a tube were added successively 1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (example BJ, 0.05 g, 0.1 mmol), imidazole (8.4 mg, 0.12 mmol), cesium carbonate (70 mg, 0.21 mmol), CuI (4 mg, 0.02 mmol), 1,10-phenanthroline (7.3 mg, 0.04 mmol) and dioxane (0.2 ml). The mixture was heated under argon at 120° C. for 12 hours. The reaction mixture was cooled to room temperature and quenched with water/ethyl acetate. The aqueous layer was extracted twice with ethylacetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: CH2Cl2/methanol: 0-5% to provide the title compound as a brown solid (20 mg, 40%), MS (m/e): 478.4 (M+H, 100%)

Fuente