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

HRID 1430033
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1430033
FC(F)(F)S([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:32]3=[N:33][CH:34]=[C:35](O)[CH:36]=[C:31]3[N:30]([CH2:38][CH3:39])[C:29]2=[O:40])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Cl-].[Ca+2]>CN(C=O)C>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[C:32]3=[N:33][CH:34]=[C:35]([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])[CH:36]=[C:31]3[N:30]([CH2:38][CH3:39])[C:29]2=[O:40])=[CH:26][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl 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 585777333-[4-(benzyloxy)phenyl]-1-ethyl-6-(2,2,2-trifluoroethoxy)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,2,2-Trifluoroethyl trifluoromethanesulfonate (0.144 mL) 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]-1-ethyl-6-(2,2,2-trifluoroethoxy)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (308 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-b630b74be857489aaf8224a13ff7d6db
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08940758B2

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