Ethyl 2-pyridinecarboxylate → (1H-pyrazol-4-yl)-pyridin-2-ylmethanone

HRID 215767

Reaktionsgleichung

Reaktionsgleichung von HRID 215767
I[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([Li])CCC.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](OCC)=[O:19]>O1CCCC1.CCCCCC.[Cl-].[NH4+]>[NH:4]1[CH:3]=[C:2]([C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)=[O:19])[CH:6]=[N:5]1

Komponenten

7

Edukt 3

HCID 17307Ethyl 2-pyridinecarboxylateHCID 770224-IodopyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 15163295(1H-pyrazol-4-yl)-pyridin-2-ylmethanoneAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 4-iodopyrazole (1.0 g) in tetrahydrofuran (10 mL), a solution of n-butyllithium in hexane (2.6 M, 4.8 mL) was added dropwise at −10° C. and stirred at room temperature for 1 hour. The reaction mixture was cooled to −10° C. and ethyl picolinate (0.86 g) was added thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was diluted with saturated aqueous ammonium chloride and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1 to 1:2) to give the titled compound (0.090 g) as a colorless solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to −10° C.
  2. stirringby stirring at room temperature for 1.5 hours
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-10d50cd5288f4eca8dff9b9dfd123049
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193176B2

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