Reacción #2487417

Ecuación de reacción

2-bromopyridine

dibenzo[b,d]furan-4-ylboronic acid

potassium phosphate tribasic monohydrate

toluene

→

product

Rendimiento 62.2%

4-(2-pyridyl)dibenzo[b,d]furan

Rendimiento 62.2%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was degassed with N2 for 20 minutes
2. 2
   Temperaturathe reaction mixture was refluxed for 18 h
3. 3
   TemperaturaAfter cooling
4. 4
   Otrothe aqueous layer was removed
5. 5
   Otrotoluene was evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   Lavadoeluting with dichloromethane
8. 8
   OtroThe crude product was chromatographed on silica gel with 20-25% ethyl acetate in hexane

Procedimiento

To a 1 L round-bottom flask was added 2-bromopyridine (13.80 mL, 142 mmol), dibenzo[b,d]furan-4-ylboronic acid (25 g, 118 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.936 g, 4.72 mmol) and potassium phosphate tribasic monohydrate (81 g, 354 mmol) with toluene (350 mL) and water (35 mL). The reaction mixture was degassed with N2 for 20 minutes. Pd2(dba)3 (2.16 g, 2.35 mmol) was added and the reaction mixture was refluxed for 18 h. Completion of the reaction was confirmed by HPLC, GC and TLC. After cooling, the aqueous layer was removed and toluene was evaporated under reduced pressure. The residue was dissolved in dichloromethane and passed through one inch silica gel plug on a frit, eluting with dichloromethane. The crude product was chromatographed on silica gel with 20-25% ethyl acetate in hexane to give 18 g (62%) of the product. The product was confirmed by HPLC (99.6% purity) and GC/MS.

Fuente