Methyl iodide → 5-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole

HRID 1009362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009362
O.[Na].[F:3][C:4]1[CH:31]=[CH:30][C:7]([CH2:8][C:9]2[NH:13][C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)=[N:11][N:10]=2)=[CH:6][CH:5]=1.IC.O.[C:35](=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[N:10]([CH3:35])[N:11]=[C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)[N:13]=2)=[CH:30][CH:31]=1.[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[N:13]=[C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)[N:11]([CH3:35])[N:10]=2)=[CH:30][CH:31]=1

Komponenten

8

Edukt 4

HCID 6328Methyl iodideHCID 71353970Sodium monohydrateHCID 86585896Sodium bicarbonate waterHCID 178489917HCID 178489917, Verbindung

Produkt 2

HCID 248526785-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazoleHCID 248527803-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydrate (containing mineral oil at 60%, 6 mg) was added to a solution of 3-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-4H-[1,2,4]triazole (18 mg) in THF (1 mL), and the reaction solution was stirred at room temperature for 30 minutes. Iodomethane (20 mg) was added to the reaction solution, and the reaction solution was then stirred at room temperature for 1.5 hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate:ethanol=9:1) to obtain 6 mg of 5-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole and 2 mg of 3-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole.

Aufarbeitung

  1. stirringthe reaction solution was then stirred at room temperature for 1.5 hours
  2. customthe organic layer was separated
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate:ethanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-0382d362e38145b9bd07403c8e4b99b1
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973033B2

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