N,N-Dimethylglycine → 1-(1-Methyl-1H-imidazol-4-yl)-1H-pyrazole-4-carbaldehyde

HRID 220488

Reaktionsgleichung

Reaktionsgleichung von HRID 220488
Br[C:2]1[N:3]=[CH:4][N:5]([CH3:7])[CH:6]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:21]1[CH:25]=[C:24]([CH:26]=[O:27])[CH:23]=[N:22]1>[Cu]I.CS(C)=O>[CH3:7][N:5]1[CH:6]=[C:2]([N:21]2[CH:25]=[C:24]([CH:26]=[O:27])[CH:23]=[N:22]2)[N:3]=[CH:4]1

Komponenten

7

Edukt 4

HCID 673N,N-Dimethylglycine2×HCID 11430Potassium Carbonate2×HCID 12776534-Bromo-1-methyl-1H-imidazoleHCID 51306731H-pyrazole-4-carbaldehyde

Produkt 1

HCID 866416551-(1-Methyl-1H-imidazol-4-yl)-1H-pyrazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator2×HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In an oven-dried flask, combine 4-bromo-1-methyl-1H-imidazole (0.200 g, 1.24 mmol), copper (I) iodide (0.022 g, 0.113 mmol), N,N-dimethylglycine (0.023 g, 0.226 mmol), and potassium carbonate (0.312 g, 2.26 mmol). Purge with nitrogen 3 times. Add 1-H-pyrazole-4-carboxaldehyde (0.109 g, 1.13 mmol), and DMSO (1.7 mL). Heat to 110° C. for 48 hr. Cool to ambient temperature and partition between ethyl acetate and water. Separate organic layer and extract aqueous layer twice with ethyl acetate. Dry combined organic layers (magnesium sulfate), filter and concentrate. Add copper (I) iodide (0.022 g, 0.113 mmol), N,N-dimethylglycine (0.023 g, 0.226 mmol), potassium carbonate (0.312 g, 2.26 mmol), and DMSO (1.7 mL). Purge with nitrogen 3 times. Heat to 110° C. for 18 hr. Cool to ambient temperature and partition between ethyl acetate and water. Separate organic layer and extract aqueous layer twice with ethyl acetate. Dry combined organic layers (magnesium sulfate), filter, concentrate, and purify (silica gel chromatography, eluting with 50:50 to 100:0 ethyl acetate:hexanes) to give the title preparation (39 mg, 20%). GC-MS: m/z=176 [M+].

Aufarbeitung

  1. customIn an oven-dried flask, combine
  2. customPurge with nitrogen 3 times
  3. temperatureCool to ambient temperature
  4. custompartition between ethyl acetate and water
  5. extractionSeparate organic layer and extract aqueous layer twice with ethyl acetate
  6. customDry
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurge with nitrogen 3 times
  10. temperatureHeat to 110° C. for 18 hr
  11. temperatureCool to ambient temperature
  12. custompartition between ethyl acetate and water
  13. extractionSeparate organic layer and extract aqueous layer twice with ethyl acetate
  14. customDry
  15. filtrationfilter
  16. concentrationconcentrate
  17. custompurify
  18. wash(silica gel chromatography, eluting with 50:50 to 100:0 ethyl acetate:hexanes)
  19. customto give the title
  20. custompreparation (39 mg, 20%)

Quellen und Nachweise

ORD-Eintrag
ord-404b455f927940d59c2b571efdfb5d06
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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