Potassium Carbonate → Ethyl 3-[4-bromo-6-(trifluoromethyl)-1H-benzimidazol-1-yl]-3-phenyl-2-propenoate

HRID 1676028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676028
[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:21]1([C:27]#[C:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:27]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:6]=2[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 178506062HCID 178506062, Verbindung

Produkt 1

HCID 67352946Ethyl 3-[4-bromo-6-(trifluoromethyl)-1H-benzimidazol-1-yl]-3-phenyl-2-propenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-bromo-6-trifluoromethylbenzimidazole (1.00 g, 3.77 mmol) in DMF (10 mL) was added potassium carbonate (520 mg, 3.77 mmol) and ethyl phenylpropiolate (690 μL, 4.15 mmol). The suspension was then warmed to 100° C. for 4 hours, cooled to room temperature, and was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (99:1), to afford the title compound as a mixture of geometric isomers (ca. 6:1 as determined by 1H NMR). 1H NMR: (CDCl3) of the mixture, 8.16 (s), 8.13 (s), 7.76 (br), 7.57-7.17 (m), 6.61 (s), 6.30 (s), 4.18 (q, J=7.32), 4.07 (q, J=7.32), 1.21 (t, J=7.32), 1.10 (t, J=7.32).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customwas evaporated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and methanol (99:1)

Quellen und Nachweise

ORD-Eintrag
ord-acc81003028a42fca8aeecd74cf3371c
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003806B2

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