Reacción #70849

Ecuación de reacción

2-(3-Bromopropoxy)tetrahydropyran

4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

KOH

water

→

desired compound

Rendimiento 54.0%

4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-2-[3-(tetrahydropyran-2-yloxy)propyl]pyrazolo[3,4-b]pyridine

Rendimiento 54.0%

Disolventes

toluene

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool
2. 2
   Otrothe phases were separated
3. 3
   ExtracciónThe aqueous phase was extracted with EtOAc
4. 4
   SecadoThe organic phase was dried over Na2SO4
5. 5
   Concentraciónconcentrated to dryness
6. 6
   OtroThe crude product obtained
7. 7
   Otrowas purified by chromatography on silica gel
8. 8
   Temperaturaof increasing polarity as eluent

Procedimiento

A suspension of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.30 g, 0.8 mmol, obtained in example 1), KOH (0.05 g, 0.8 mmol) and crown ether 18-C-6 (0.01 g, 0.03 mmol) in toluene (10 mL) was heated to 100° C. for 1 h. 2-(3-Bromopropoxy)tetrahydropyran (0.17 g, 0.8 mmol) was added and stirred at 100° C. for 24 h. It was allowed to cool, water and EtOAc were added and the phases were separated. The aqueous phase was extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.22 g of the desired compound (yield: 54%).

Fuente