8-Hydroxyquinoline → 1-Phenyl-1H-pyrrolo[3,2-b]pyridine

HRID 2039815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039815
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O[C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+].IC1C=CC=CC=1.[OH-].[NH4+]>CS(C)=O.[Cu]I.CC(=O)OCC>[C:11]1([N:1]2[C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:20]=1

Komponenten

9

Edukt 5

HCID 19238-HydroxyquinolineHCID 92264-AzaindoleHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 14923Ammonium Hydroxide

Produkt 1

HCID 210839631-Phenyl-1H-pyrrolo[3,2-b]pyridineAusbeute 188,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a mixture of 4-azaindole (1.20 g, 10.2 mmol), copper(I) iodide (290 mg, 1.53 mmol), 8-hydroxyquinoline (221 mg, 1.53 mmol) and potassium carbonate (1.55 g, 11.2 mmol) in DMSO (24 ml) was added iodobenzene (1.25 ml, 11.2 mmol). The reaction mixture was stirred at 130° C. for 3 h. The mixture was then cooled to room temperature and a solution of ammonium hydroxide (10% in water) and EA were added. The organic layer was separated, washed twice with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography on silica gel (EA/HEP) gave 560 mg of the title compound.

Aufarbeitung

  1. temperatureThe mixture was then cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-81bb0f9394474220ae56e786b368d364
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580813B2

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