Reaktion #70849

Reaktionsgleichung

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

Ausbeute 54.0%

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

Ausbeute 54.0%

Lösungsmittel

toluene

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   Sonstigethe phases were separated
3. 3
   ExtraktionThe aqueous phase was extracted with EtOAc
4. 4
   TrocknenThe organic phase was dried over Na2SO4
5. 5
   Einengenconcentrated to dryness
6. 6
   SonstigeThe crude product obtained
7. 7
   Sonstigewas purified by chromatography on silica gel
8. 8
   Temperaturof increasing polarity as eluent

Vorschrift

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%).

Quelle