Ethyl Acetate → Ethyl 1-(3-trifluoromethylbenzyl)-1H-indole-2-carboxylate

HRID 131639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131639
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:15][C:16]([F:25])([F:26])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 73125Ethyl indole-2-carboxylateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzene

Produkt 1

HCID 68696914Ethyl 1-(3-trifluoromethylbenzyl)-1H-indole-2-carboxylateAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 0.492 g (2.6 mmol) of ethyl 1H-indole-2-carboxylate, of 0.683 g (2.86 mmol) of 3-trifluoromethylbenzyl bromide and of 0.898 g (6.5 mmol) of potassium carbonate in 50 ml of dimethylformamide is stirred at 60° C. for 24 hours. The reaction mixture is cooled and is poured into a mixture of ice-cold water and of ethyl acetate. After settling, the organic phase is separated and is then washed with two times 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The solution is dried over magnesium sulfate and filtered, and then the filtrate is concentrated under reduced pressure. 0.8 g of an oil is obtained, which oil is used as is in the following stage.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customthe organic phase is separated
  3. washis then washed with two times 50 ml of water
  4. dry with materialThe solution is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-71a17d272be949999e799a2ef03f718c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384969B2

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