Potassium Carbonate → 3-methoxycarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole

HRID 1869154

Reaktionsgleichung

Reaktionsgleichung von HRID 1869154
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1.[CH3:22][O:23][C:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)=[O:25]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:22][O:23][C:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[CH:27]=1)=[O:25]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 589098Methyl indole-3-carboxylateHCID 27367094-Chloro-2-(trifluoromethyl)quinoline

Produkt 1

HCID 689705923-methoxycarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indoleAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1.04 g (7.5 mmol) of potassium carbonate and 0.695 g (3 mmol) of 4-chloro-2-(trifluoromethyl)quinoline are added to 0.526 g (3 mmol) of 3-methoxycarbonyl-1H-indole in 10 cm3 of dimethylformamide under an argon atmosphere. After stirring at a temperature in the region of 100° C. for 20 hours, the reaction mixture is cooled and diluted with 100 cm3 of ethyl acetate and 100 cm3 of water. The organic phase is separated off by settling and washed with twice 100 cm3 of water and 100 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), resulting in an orange-coloured oil. This oil is triturated in 20 cm3 of isopropyl ether and the resulting precipitate is filtered off, giving 0.6 g of 3-methoxycarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole in the form of a yellow powder. Mass spectrum (EI): m/e 370 (M+•), m/e 339.

Aufarbeitung

  1. temperaturethe reaction mixture is cooled
  2. customThe organic phase is separated off by settling
  3. washwashed with twice 100 cm3 of water and 100 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. customresulting in an orange-coloured oil
  8. customThis oil is triturated in 20 cm3 of isopropyl ether
  9. filtrationthe resulting precipitate is filtered off

Quellen und Nachweise

ORD-Eintrag
ord-69445a605d934814a3a5766549698cb2
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638521B2

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