تفاعل #70442

معادلة التفاعل

5-bromo-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidine

isopropenylboronic acid pinacol ester

cesium carbonate

→

title compound

المردود 79.9%

5-Isopropenyl-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidine

المردود 79.9%

المذيبات

N,N-dimethylformamide

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool to room temperature
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

الإجراء التجريبي

To a solution of 5-bromo-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidine (Example 57) (31 mg, 0.062 mmol) and isopropenylboronic acid pinacol ester (23 μL, 0.124 mmol) in dry N,N-dimethylformamide (0.3 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (complex with dichloromethane) (1 mg, 0.012 mmol) and cesium carbonate (40 mg, 0.124 mmol). The mixture was stirred at 90° C. overnight under N2, allowed to cool to room temperature, diluted with water (1 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound as a white crystal (23 mg, yield 78%).

المصدر