Potassium Carbonate → 5-Methoxy-1-phenyl-1H-indole

HRID 1510077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510077
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].I[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:7]=[CH:6]2

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 138725-MethoxyindoleHCID 145742L-Proline

Produkt 1

HCID 136034295-Methoxy-1-phenyl-1H-indoleAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

To a mixture of 5-methoxyindole (1.00 g, 6.79 mmol), copper(I) iodide (129 mg, 0.68 mmol), L-proline (156 mg, 1.36 mmol) and potassium carbonate (1.88 g, 13.6 mmol) in DMSO (7.5 ml) was added iodobenzene (0.76 ml, 6.79 mmol). The reaction mixture was stirred for 10 h at 125° C. in a microwave reactor. The mixture was then quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/HEP 1:15). 951 mg of the title compound were obtained.

Aufarbeitung

  1. customThe mixture was then quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (EA/HEP 1:15)

Quellen und Nachweise

ORD-Eintrag
ord-bbe2d10967f7493cae6f06ed057b4501
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211885B2

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