Cesium carbonate → HCID 22026619, Verbindung

HRID 1516035

Reaktionsgleichung

Reaktionsgleichung von HRID 1516035
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]>[C:13]1([N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 5893132-(1H-imidazol-2-yl)pyridine

Produkt 1

HCID 22026619HCID 22026619, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(1H-imidazol-2-yl)pyridine (6.91 g), iodobenzene (11.47 g), Cs2CO3 (25 g), and copper powder (15 g) were combined in 60 mL anhydrous DMF in a 250 mL round bottom flask equipped with a magnetic stirrer and a reflux condenser. The mixture was degassed with N2 for 15 minutes at room temperature and then refluxed under N2 in an oil bath for 24 hours. The resulting mixture was cooled to room temperature and suction-filtered to remove the solid byproduct. The filtrate was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (2×100 mL), then with saturated NaCl (2×150 mL), and subsequently dried with anhydrous Na2SO4. Evaporation of the solvent gave crude 2-(1-phenyl-1H-imidazol-2-yl)pyridine. The crude product is generally pure enough to use in making redox mediators, although the crude product may be further purified using a silica gel column and eluting with MeOH/CHCl3.

Aufarbeitung

  1. customequipped with a magnetic stirrer and a reflux condenser
  2. customThe mixture was degassed with N2 for 15 minutes at room temperature
  3. temperaturerefluxed under N2 in an oil bath for 24 hours
  4. filtrationsuction-filtered
  5. customto remove the solid byproduct
  6. extractionThe filtrate was extracted with EtOAc (3×100 mL)
  7. washThe combined organic layers were washed with H2O (2×100 mL)
  8. dry with materialwith saturated NaCl (2×150 mL), and subsequently dried with anhydrous Na2SO4
  9. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-9327134f974c41df85bd4ea55634b42f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08226814B2

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