Réaction #969896

Équation de réaction

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

Rendement 84.0%

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   SéchageThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Concentrationconcentrated in vacuo
4. 4
   AutreThe obtained residue was purified

Mode opératoire

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.

Source