Reaktion #2487418

Reaktionsgleichung

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

Ausbeute 87.0%

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

Ausbeute 87.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was degassed with nitrogen for 20 minutes
2. 2
   Temperaturheated
3. 3
   Temperaturto reflux for 24 h
4. 4
   TemperaturAfter cooling
5. 5
   Sonstigethe organic layer was separated
6. 6
   Extraktionthe aqueous layer extracted 3×50 mL with dichloromethane
7. 7
   Trocknendried over sodium sulfate
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe crude product was chromatographed on silica gel with 5% dichloromethane in hexane

Vorschrift

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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