Reaktion #62366

Reaktionsgleichung

cesium carbonate

benzophenoneimine

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

5-bromo-2-chloro-4-methylpyridine

→

title compound

2-Chloro-4-methylpyridin-5-ylamine

Lösungsmittel

brine

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   Extraktionextracted with ethylacetate
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Sonstigethe 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
   Extraktionextracted with ethyl acetate
9. 9
   Waschenthe organic layer was washed with saturated brine
10. 10
    Trocknendried over magnesium sulfate
11. 11
    SonstigeThe solvent was evaporated
12. 12
    Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Vorschrift

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.

Quelle