Реакция #2487418

Уравнение реакции

2-([1,1′-Biphenyl]-3-yl)-5-bromo-4-methylpyridine

2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane

potassium phosphate tribasic monohydrate

toluene

→

product

Выход 87.0%

2-([1,1′-biphenyl]-3-yl)-4,5-dimethylpyridine

Выход 87.0%

Растворители

water

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was degassed with nitrogen for 20 minutes
2. 2
   Температураheated
3. 3
   Температураto reflux for 24 h
4. 4
   ТемператураAfter cooling
5. 5
   Другоеthe organic layer was separated
6. 6
   Экстракцияthe aqueous layer extracted 3×50 mL with dichloromethane
7. 7
   Сушкаdried over sodium sulfate
8. 8
   Другоеevaporated
9. 9
   ДругоеThe crude product was chromatographed on silica gel with 5% dichloromethane in hexane

Методика

2-([1,1′-Biphenyl]-3-yl)-5-bromo-4-methylpyridine 11.5 g (35.5 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5.57 g, 44.3 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (1.2 g, 2.84 mmol), Pd2dba3 (0.650 g, 0.709 mmol) and potassium phosphate tribasic monohydrate, 250 mL toluene and 25 mL of water were placed in flask under nitrogen. The reaction mixture was degassed with nitrogen for 20 minutes and heated to reflux for 24 h. After cooling, the organic layer was separated and the aqueous layer extracted 3×50 mL with dichloromethane, dried over sodium sulfate and evaporated. The crude product was chromatographed on silica gel with 5% dichloromethane in hexane to give 8.0 g (87%) of the product. The product was confirmed by NMR and GC/MS.

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