Acetonitrile → methyl 2-fluoro-5-nitro-4-[2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-1-yl]benzoate

HRID 1396672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396672
[F:1][C:2]1[CH:11]=[C:10](F)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(#N)C.C(N(CC)CC)C.[O:26]1[CH2:31][CH2:30][CH:29]([C:32]2[NH:33][CH:34]=[CH:35][N:36]=2)[CH2:28][CH2:27]1>C(OCC)(=O)C.O>[F:1][C:2]1[CH:11]=[C:10]([N:33]2[CH:34]=[CH:35][N:36]=[C:32]2[CH:29]2[CH2:30][CH2:31][O:26][CH2:27][CH2:28]2)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 11447263Methyl 2,4-difluoro-5-nitrobenzoateHCID 591985871033717-12-2

Produkt 1

HCID 68019147methyl 2-fluoro-5-nitro-4-[2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-1-yl]benzoateAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 4.10 g of methyl 2,4-difluoro-5-nitrobenzoate and 40 mL of acetonitrile was added 4.76 mL of triethylamine, and 2.60 g of 2-(tetrahydro-2H-pyran-4-yl)-1H-imidazole was gradually added thereto under ice-cooling, followed by stirring at room temperature for 4 hours. To the reaction mixture were added water and ethyl acetate, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 3.84 g of methyl 2-fluoro-5-nitro-4-[2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-1-yl]benzoate as a yellow solid.

Aufarbeitung

  1. additionwas gradually added
  2. temperatureunder ice-cooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-44ea935903a74e8e940841265925fb6a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901126B2

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