反応 #2487418

反応方程式

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

収率 87.0%

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

収率 87.0%

溶媒

water

反応条件

後処理

1. 1
   その他The reaction mixture was degassed with nitrogen for 20 minutes
2. 2
   温度heated
3. 3
   温度to reflux for 24 h
4. 4
   温度After cooling
5. 5
   その他the organic layer was separated
6. 6
   抽出the aqueous layer extracted 3×50 mL with dichloromethane
7. 7
   乾燥dried over sodium sulfate
8. 8
   その他evaporated
9. 9
   その他The crude product was chromatographed on silica gel with 5% dichloromethane in hexane

実験手順

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.

出典