반응 #62366

반응 방정식

cesium carbonate

benzophenoneimine

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

5-bromo-2-chloro-4-methylpyridine

→

title compound

2-Chloro-4-methylpyridin-5-ylamine

용매

brine

toluene

반응 조건

후처리

1. 1
   온도to cool to room temperature
2. 2
   추출extracted with ethylacetate
3. 3
   건조dried over magnesium sulfate
4. 4
   기타the solvent was evaporated
5. 5
   workup.ADDITIONThe residue was added with 10 mL of tetrahydrofuran and 10 mL of 5N hydrochloric acid
6. 6
   workup.STIRRINGstirred at room temperature for 1 hour
7. 7
   workup.ADDITIONThe reaction solution was added with aqueous sodium hydrogen carbonate
8. 8
   추출extracted with ethyl acetate
9. 9
   세척the organic layer was washed with saturated brine
10. 10
    건조dried over magnesium sulfate
11. 11
    기타The solvent was evaporated
12. 12
    기타the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

실험 절차

308 mg of 5-bromo-2-chloro-4-methylpyridine was dissolved in 6 mL of toluene, added with 680 mg cesium carbonate, 0.3 mL of benzophenoneimine, 42 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl and 46 mg of tris(dibenzylideneacetone)bis palladium, and stirred under nitrogen atmosphere at 110° C. for 15 hours. The reaction solution was allowed to cool to room temperature, then added with saturated brine, extracted with ethylacetate, dried over magnesium sulfate, and then the solvent was evaporated. The residue was added with 10 mL of tetrahydrofuran and 10 mL of 5N hydrochloric acid, and stirred at room temperature for 1 hour. The reaction solution was added with aqueous sodium hydrogen carbonate, extracted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), to afford 56 mg of the title compound.

출처