Reacción #45731

Ecuación de reacción

ammonium chloride

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

2,3-difluorophenylboronic acid

tripotassium phosphate

→

compound

Rendimiento 53.0%

2-Cyclopropyl-6-(2,3-difluorophenyl)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Rendimiento 53.0%

Disolventes

ethyl acetate

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   ExtracciónThe aqueous layer was extracted twice with ethyl acetate
3. 3
   Lavadowashed with saturated brine
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   OtroThe solvent was evaporated away
6. 6
   Otrothe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=9:1)

Procedimiento

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (190 mg, 0.64 mmol), 2,3-difluorophenylboronic acid (407 mg, 2.58 mmol) and tripotassium phosphate (274 mg, 1.29 mmol) were dissolved in 1,4-dioxane (6 ml), then at room temperature, tetrakis(triphenylphosphine)palladium(0) (149 mg, 0.13 mmol) was added. The suspension was stirred under nitrogen atmosphere at 95° C. for 86 hours. After cooling to room temperature, the solution was fractionated with ethyl acetate and aqueous saturated ammonium chloride solution. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=9:1) to obtain the entitled compound (111 mg, 53%) as a white solid.

Fuente