1,10-Phenanthroline → 1-Phenyl-1H-indole-6-carbaldehyde

HRID 1371848

Reaktionsgleichung

Reaktionsgleichung von HRID 1371848
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.N1[C:25]2[C:16](=[CH:17][CH:18]=[C:19]3[C:24]=2N=CC=C3)C=CC=1.C(=CC(/C=C/C1C=CC=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].IC1C=CC=CC=1>C1(C)C(C)=CC=CC=1.ClCCl.[Cl-].[NH4+]>[C:16]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=3)[CH:3]=[CH:2]2)[CH:25]=[CH:24][CH:19]=[CH:18][CH:17]=1

Komponenten

9

Edukt 5

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 27734351H-Indole-6-carboxaldehydeHCID 5354370trans-Dibenzylideneacetone

Produkt 1

HCID 210713941-Phenyl-1H-indole-6-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 7237O-XyleneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Combine in a sealed tube 1H-indole-6-carbaldehyde 0.9 g, 6.2 mmol), copper(I) trifluoromethanesulfate—complex (0.2 g, 0.3 mmol), phenanthroline (1.3 g, 6.2 mmol), transdibenzylidenacetone (0.1 g, 0.3 mmol), cesium carbonate (2.6 g, 7.9 mmol) and iodobenzene (1.6 ml, 14.3 mmol) in xylene (40 ml). Heat at about 110° C. After 24 hours, cool to room temperature, dilute with dichloromethane and saturated ammonium chloride. Separate the layer and Extract the aqueous layer with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrated to give a residue. Chromatograph the residue eluting with 8:2 hexane:EtOAc to give the title compound.

Aufarbeitung

  1. temperaturecool to room temperature
  2. customSeparate the layer
  3. extractionExtract the aqueous layer with dichloromethane
  4. washwash sequentially with distilled water and brine
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrated
  8. customto give a residue
  9. washChromatograph the residue eluting with 8:2 hexane

Quellen und Nachweise

ORD-Eintrag
ord-463b9612b6b44288b2f7c6f4e2f531bb
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157488B2

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