Réaction #2487418

Équation de réaction

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

Rendement 87.0%

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

Rendement 87.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was degassed with nitrogen for 20 minutes
2. 2
   Températureheated
3. 3
   Températureto reflux for 24 h
4. 4
   TempératureAfter cooling
5. 5
   Autrethe organic layer was separated
6. 6
   Extractionthe aqueous layer extracted 3×50 mL with dichloromethane
7. 7
   Séchagedried over sodium sulfate
8. 8
   Autreevaporated
9. 9
   AutreThe crude product was chromatographed on silica gel with 5% dichloromethane in hexane

Mode opératoire

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.

Source