Reacción #969896

Ecuación de reacción

phenyl boronic acid

potassium phosphate

1,4-dioxane

4-[1-(4-bromophenyl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one

4-[1-(4-bromophenyl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one

water

→

4-[1-(biphenyl-4-yl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one

Rendimiento 84.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   SecadoThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   OtroThe obtained residue was purified

Procedimiento

A solution of 4-[1-(4-bromophenyl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one (12.2 mg, 0.0285 mmol) in 1,4-dioxane (3 mL) prepared in Example 75 was added with tetrakis(triphenylphosphine) palladium (1.6 mg, 1.4 μmol), phenyl boronic acid (7 mg, 0.057 mmol), and potassium phosphate (30 mg, 0.142 mmol) at room temperature, and the resultant was stirred at 100° C. for 20 hours. The reaction solution was poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using thin-layer chromatography (hexane:ethyl acetate=3:1), and 4-[1-(biphenyl-4-yl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one (10.2 mg, 84%) was obtained as a white amorphous solid.

Fuente