Reaction #70849

Reaction equation

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

Yield 54.0%

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

Yield 54.0%

Solvents

toluene

EtOAc

Conditions

Workup

1. 1
   Temperatureto cool
2. 2
   Otherthe phases were separated
3. 3
   ExtractionThe aqueous phase was extracted with EtOAc
4. 4
   DryingThe organic phase was dried over Na2SO4
5. 5
   Concentrationconcentrated to dryness
6. 6
   OtherThe crude product obtained
7. 7
   Otherwas purified by chromatography on silica gel
8. 8
   Temperatureof increasing polarity as eluent

Procedure

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%).

Source