Réaction #169857

Équation de réaction

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

1,1′-carbonylbis(1H-imidazole)

Cs2CO3

1,1′-carbonylbis(1H-imidazole)

water

→

title compound

Rendement 69.3%

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

Rendement 69.3%

Solvants

DME

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred at 100° C. for 10 min
2. 2
   Extractionextracted with AcOEt
3. 3
   SéchageThe organic layer was dried over MgSO4
4. 4
   Concentrationconcentrated 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
   Extractionextracted with AcOEt
10. 10
    SéchageThe organic layer was dried over MgSO4
11. 11
    Concentrationconcentrated 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
    Filtrationfiltered
16. 16
    Autreevaporated
17. 17
    AutreThe residue was chromatographed on silica gel eluting with AcOEt/Hexane

Mode opératoire

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).

Source