Reaktion #70875

Reaktionsgleichung

2-[4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]acetaldehyde

2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]acetaldehyde

sodium triacetoxyborohydride

4-hydroxypiperidine

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title compound

Ausbeute 20.0%

1-[2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]ethyl]piperidin-4-ol

Ausbeute 20.0%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenIt was concentrated
2. 2
   workup.ADDITIONa mixture of water and EtOAc
3. 3
   workup.ADDITIONwere added
4. 4
   SonstigeThe phases were separated
5. 5
   ExtraktionThe aqueous phase was extracted with EtOAc
6. 6
   TrocknenThe organic phase was dried over Na2SO4
7. 7
   Einengenconcentrated to dryness
8. 8
   SonstigeThe crude product obtained
9. 9
   Sonstigewas purified by chromatography on silica gel using
10. 10
    Temperaturincreasing polarity mixtures of EtOAc-MeOH as eluent

Vorschrift

In a volumetric flask, 2-[4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]acetaldehyde (0.08 g, 0.2 mmol, obtained in example 94), sodium triacetoxyborohydride (0.08 g, 0.4 mmol), 4-hydroxypiperidine (0.02 g, 0.2 mmol) and 1,2-dichloroethane (3 mL) were introduced under argon atmosphere. The mixture was stirred overnight at room temperature. It was concentrated and a mixture of water and EtOAc were added. 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 increasing polarity mixtures of EtOAc-MeOH as eluent, to afford 19 mg of the title compound (yield: 20%).

Quelle