Potassium Carbonate → Methyl 1-(6-methoxyquinolin-4-yl)-1H-indole-3-carboxylate

HRID 1869170

Reaktionsgleichung

Reaktionsgleichung von HRID 1869170
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][CH:9]=1.[CH3:20][O:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:23]>CC(N(C)C)=O.C(OCC)(=O)C.O>[CH3:20][O:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[N:11]=[CH:10][CH:9]=2)[CH:25]=1)=[O:23]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 2283484-Chloro-6-methoxyquinolineHCID 589098Methyl indole-3-carboxylate

Produkt 1

HCID 68970220Methyl 1-(6-methoxyquinolin-4-yl)-1H-indole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

1.73 g (12.5 mmol) of potassium carbonate and 0.968 g (5 mmol) of 4-chloro-6-methoxyquinoline are added to 0.876 g (5 mmol) of 3-methoxycarbonyl-1H-indole in 20 cm3 of dimethylacetamide under an argon atmosphere. After stirring at a temperature in the region of 140° C. for 20 hours, the reaction mixture is cooled and diluted with 200 cm3 of ethyl acetate and 200 cm3 of water. The organic phase is separated off by settling and washed with three times 200 cm3 of water and 200 cm3 of saturated aqueous sodium chloride solution and then it is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (8/2 and then 7/3 by volume)]. Concentrating these fractions to dryness under reduced pressure (2.7 kPa) results in 0.7 g of 3-methoxycarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole in the form of a white powder. Mass spectrum (EI): m/e 332 (M+•), m/e 301.

Aufarbeitung

  1. temperaturethe reaction mixture is cooled
  2. customThe organic phase is separated off by settling
  3. washwashed with three times 200 cm3 of water and 200 cm3 of saturated aqueous sodium chloride solution
  4. dry with materialit is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue obtained
  8. customis purified by flash chromatography [eluent
  9. concentrationConcentrating these fractions to dryness under reduced pressure (2.7 kPa)
  10. customresults in 0.7 g of 3-methoxycarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole in the form of a white powder

Quellen und Nachweise

ORD-Eintrag
ord-a644d3714b874741bd73fd5fe5905fa4
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638521B2

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