Reacción #70852

Ecuación de reacción

1-chloromethyl-4-(methylsulfanyl)benzene

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

→

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

Rendimiento 25.0%

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

Rendimiento 47.0%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool
2. 2
   Concentraciónconcentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in a mixture of water and EtOAc
4. 4
   OtroThe two phases were separated
5. 5
   SecadoThe organic phase was dried over Na2SO4
6. 6
   Concentraciónconcentrated to dryness
7. 7
   OtroThe crude product obtained
8. 8
   Otrowas purified by chromatography on silica gel
9. 9
   Temperaturaof increasing polarity as eluent

Procedimiento

In a volumetric flask, 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.30 g, 78.0 mmol, obtained in example 1) and DMF (3.5 mL) were introduced under argon atmosphere. KOH (0.06 g, 1.1 mmol) was added followed by a solution of 1-chloromethyl-4-(methylsulfanyl)benzene (0.15 g, 0.9 mmol, obtained in section a) in DMF (0.4 mL). This was heated to 60° C. overnight. It was allowed to cool and concentrated. The residue was dissolved in a mixture of water and EtOAc. The two phases were separated. 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 0.10 g of 4,6-bis(4-fluorophenyl)-2-(4-methylsulfanylbenzyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 25%) and 0.19 g of 4,6-bis(4-fluorophenyl)-1-(4-methylsulfanylbenzyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 47%).

Fuente