반응 #62341

반응 방정식

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

용매

toluene

반응 조건

후처리

1. 1
   온도to cool to room temperature
2. 2
   기타the 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
   기타The resultant reaction solution
6. 6
   추출extracted with ethyl acetate
7. 7
   세척the organic layer was washed with water
8. 8
   건조dried over magnesium sulfate
9. 9
   기타The solvent was evaporated
10. 10
    기타the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

실험 절차

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.

출처