반응 #1131477

반응 방정식

N2-[4-(benzyloxy)phenyl]-5-fluoropyridine-2,3-diamine

1,1′-carbonylbis(1H-imidazole)

Cs2CO3

1,1′-carbonylbis(1H-imidazole)

water

→

title compound

수율 69.3%

1-ethyl-6-fluoro-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

수율 69.3%

용매

DME

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at 100° C. for 10 min
2. 2
   추출extracted with AcOEt
3. 3
   건조The organic layer was dried over MgSO4
4. 4
   농축concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in DMF (10 mL)
6. 6
   workup.ADDITIONCs2CO3 (3.58 g) and iodoethane (1.29 g) were added successively
7. 7
   workup.STIRRINGThe mixture was stirred at 100° C. for 2 h
8. 8
   workup.ADDITIONtreated with water
9. 9
   추출extracted with AcOEt
10. 10
    건조The organic layer was dried over MgSO4
11. 11
    농축concentrated in vacuo
12. 12
    workup.DISSOLUTIONThe residue was dissolved in EtOH (30 ml)
13. 13
    workup.ADDITIONPd/C (1.5 g) was added
14. 14
    workup.STIRRINGUnder H2 atmosphere, the mixture was stirred at room temperature for 30 min
15. 15
    여과filtered
16. 16
    기타evaporated
17. 17
    기타The residue was chromatographed on silica gel eluting with AcOEt/Hexane

실험 절차

A mixture of N2-[4-(benzyloxy)phenyl]-5-fluoropyridine-2,3-diamine (0.85 g) and 1,1′-carbonylbis(1H-imidazole) (0.45 g) in DME (10 mL) was stirred at 100° C. for 4 h, and then Cs2CO3 (0.90 g) and 1,1′-carbonylbis(1H-imidazole) (0.892 g) were added successively. The mixture was stirred at 100° C. for 10 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in DMF (10 mL), and then Cs2CO3 (3.58 g) and iodoethane (1.29 g) were added successively. The mixture was stirred at 100° C. for 2 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in EtOH (30 ml), and Pd/C (1.5 g) was added. Under H2 atmosphere, the mixture was stirred at room temperature for 30 min, filtered and evaporated. The residue was chromatographed on silica gel eluting with AcOEt/Hexane to give the title compound (0.52 g).

출처