Reacción #2487418

Ecuación de reacción

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

Rendimiento 87.0%

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

Rendimiento 87.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was degassed with nitrogen for 20 minutes
2. 2
   Temperaturaheated
3. 3
   Temperaturato reflux for 24 h
4. 4
   TemperaturaAfter cooling
5. 5
   Otrothe organic layer was separated
6. 6
   Extracciónthe aqueous layer extracted 3×50 mL with dichloromethane
7. 7
   Secadodried over sodium sulfate
8. 8
   Otroevaporated
9. 9
   OtroThe crude product was chromatographed on silica gel with 5% dichloromethane in hexane

Procedimiento

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.

Fuente