Potassium Carbonate → 3-[4-(benzyloxy)phenyl]-6-(2,2-difluoroethoxy)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587574

Reaktionsgleichung

Reaktionsgleichung von HRID 587574
FC(F)(F)S([O:6][CH2:7][CH:8]([F:10])[F:9])(=O)=O.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:31]3=[N:32][CH:33]=[C:34](O)[CH:35]=[C:30]3[N:29]([CH2:37][CH3:38])[C:28]2=[O:39])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Cl-].[Ca+2]>CN(C=O)C>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[C:31]3=[N:32][CH:33]=[C:34]([O:6][CH2:7][CH:8]([F:10])[F:9])[CH:35]=[C:30]3[N:29]([CH2:37][CH3:38])[C:28]2=[O:39])=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 5284359Calcium ChlorideHCID 585776213-[4-(benzyloxy)phenyl]-1-ethyl-6-hydroxy-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Produkt 1

HCID 585772623-[4-(benzyloxy)phenyl]-6-(2,2-difluoroethoxy)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,2-Difluoroethyl trifluoromethanesulfonate (213 mg) was added to a solution of 3-[4-(benzyloxy)phenyl]-1-ethyl-6-hydroxy-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (300 mg) and potassium carbonate (229 mg) in DMF (5 mL) at room temperature. The mixture was stirred at ambient temperature under a dry atmosphere (CaCl2 tube) for 3 h. The mixture was quenched with water at room temperature and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 15%-50% AcOEt in hexane) to give 3-[4-(benzyloxy)phenyl]-6-(2,2-difluoroethoxy)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (301 mg) as colorless oil.

Aufarbeitung

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, eluted with 15%-50% AcOEt in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ed96abdf1d5e4001aaba674a39adc370
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226921B2

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