تفاعل #2487418

معادلة التفاعل

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

المردود 87.0%

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

المردود 87.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was degassed with nitrogen for 20 minutes
2. 2
   درجة الحرارةheated
3. 3
   درجة الحرارةto reflux for 24 h
4. 4
   درجة الحرارةAfter cooling
5. 5
   أخرىthe organic layer was separated
6. 6
   استخلاصthe aqueous layer extracted 3×50 mL with dichloromethane
7. 7
   تجفيفdried over sodium sulfate
8. 8
   أخرىevaporated
9. 9
   أخرىThe crude product was chromatographed on silica gel with 5% dichloromethane in hexane

الإجراء التجريبي

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.

المصدر