Réaction #158373

Équation de réaction

5-(4-chloro-5-fluoro-2-methoxyphenyl)-2-methyl-1,3-oxazole

2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl

→

title compound

2-fluoro-5-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzonitrile

Solvants

water

DMF

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   LavageThe extract was washed with water and saturated brine
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Autrethe solvent was evaporated under reduced pressure
5. 5
   AutreThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Mode opératoire

To a mixture of 5-(4-chloro-5-fluoro-2-methoxyphenyl)-2-methyl-1,3-oxazole (1.12 g) and zinc(II) cyanide (0.327 g) in DMF (10 mL) were added tris(dibenzylideneacetone)dipalladium(0) (212 mg) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (182 mg) at room temperature, and the mixture was stirred overnight under a nitrogen atmosphere at 130° C. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (902 mg).

Source