Reaktion #70865

Reaktionsgleichung

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

2-bromo-1,1-diethoxyethane

1-methoxy-2-(2-methoxyethoxy)ethane

→

2-(2,2-diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Ausbeute 53.0%

1-(2,2-diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Ausbeute 24.0%

Lösungsmittel

H2O EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   workup.ADDITIONwas added
3. 3
   SonstigeThe phases were separated
4. 4
   Extraktionthe aqueous phase was extracted with EtOAc
5. 5
   TrocknenThe combined organic phases were dried over Na2SO4
6. 6
   Einengenconcentrated to dryness
7. 7
   SonstigeThe crude product obtained
8. 8
   Sonstigewas purified by chromatography on silica gel
9. 9
   Temperaturof increasing polarity as eluent

Vorschrift

In a volumetric flask 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.20 g, 0.5 mmol, obtained in example 1), KOH (0.03 g, 0.5 mmol), 2-bromo-1,1-diethoxyethane (0.10 g, 0.5 mmol) and 1-methoxy-2-(2-methoxyethoxy)ethane (2 mL) were introduced under argon atmosphere. The mixture was heated to 100° C. and stirred at this temperature overnight. It was allowed to cool and a mixture of H2O-EtOAc was added. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were 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 139 mg of 2-(2,2-diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 53%) and 60 mg of 1-(2,2-diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 24%).

Quelle