Reaktion #62341

Reaktionsgleichung

sodium hydrogen carbonate

sodium t-butoxide

benzophenone imine

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

5-chloro-3-(naphthalen-2-yl)-1-trityl-1H-pyrazolo[4,3-b]pyridine

→

title compound

3-(Naphthalen-2-yl)-1-trityl-1H-pyrazolo[4,3-b]pyridin-5-ylamine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   Sonstigethe solvent evaporated
3. 3
   workup.ADDITIONthe residue was added with 5 mL of tetrahydrofuran and 0.3 mL of 5N hydrochloric acid
4. 4
   workup.STIRRINGstirred at room temperature for 1 hour
5. 5
   SonstigeThe resultant reaction solution
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   Waschenthe organic layer was washed with water
8. 8
   Trocknendried over magnesium sulfate
9. 9
   SonstigeThe solvent was evaporated
10. 10
    Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

Vorschrift

280 mg of 5-chloro-3-(naphthalen-2-yl)-1-trityl-1H-pyrazolo[4,3-b]pyridine was dissolved in 8 mL of toluene, added with 73 mg sodium t-butoxide, 180 μl of benzophenone imine, 100 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 56 mg of tris(dibenzylidene acetone)bispalladium, and stirred at 100° C. for 1.5 hours. The reaction solution was allowed to cool to room temperature, the solvent evaporated, and the residue was added with 5 mL of tetrahydrofuran and 0.3 mL of 5N hydrochloric acid and stirred at room temperature for 1 hour. The resultant reaction solution was added with aqueous sodium hydrogen carbonate, extracted with ethyl acetate, and the organic layer was washed with water and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3), to afford 220 mg of the title compound as a colorless powder.

Quelle