Imidazole → 4-(1H-imidazol-1-yl)-3-trifluoromethylbenzaldehyde

HRID 1362603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362603
CN(C=O)C.F[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[C:15]([F:18])([F:17])[F:16].C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>C(OCC)(=O)C.O>[N:25]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH:29]=[CH:28][N:27]=[CH:26]1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehyde

Produkt 1

HCID 223626404-(1H-imidazol-1-yl)-3-trifluoromethylbenzaldehydeAusbeute 2,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a DMF (2.0 mL) solution of 4-fluoro-3-trifluoromethylbenzaldehyde (400 mg), potassium carbonate (414 mg) and imidazole (136 mg) were added one by one, and the reaction solution was agitated at 80° C. for 6 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate 3:1→ethyl acetate) and 13.7 mg of 4-(1H-imidazol-1-yl)-3-trifluoromethylbenzaldehyde was obtained. Next, malonic acid (11.0 mg) and piperidine (53.0 mg) were added to an ethanol (1.0 mL) solution of the obtained aldehyde compound (13.0 mg), and the reaction solution was refluxed for 5 hours. Pyridine (2.0 mL) and malonic acid (11.0 mg) were added to the reaction solution, and the reaction solution was refluxed for one and a half hour. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and 15.0 mg of crude carboxylic acid was obtained by condensing under reduced pressure. By the same method as in Example 324, 10.7 mg of the title compound was obtained from the obtained carboxylic acid and 1-aminoindan. The physical properties of the compound are as follows.

Aufarbeitung

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate 3:1→ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-716cb00a62a84e759f6cb5de2c9c9c92
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880009B2

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