1,10-Phenanthroline → N-(4-Pyrazol-1-yl-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester

HRID 655865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655865
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[CH:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1.[C:33]([O:37][C:38]([NH:40][NH2:41])=[O:39])([CH3:36])([CH3:35])[CH3:34]>[Cu](I)I.CN(C=O)C>[C:33]([O:37][C:38]([N:40]([C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[CH:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1)[NH2:41])=[O:39])([CH3:36])([CH3:35])[CH3:34]

Komponenten

7

Edukt 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 70091tert-Butyl carbazateHCID 27764811-(4-Iodophenyl)-1H-Pyrazole

Produkt 1

HCID 68820898N-(4-Pyrazol-1-yl-phenyl)-hydrazinecarboxylic Acid tert-butyl EsterAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Copper iodide (18 mg, 0.05 eq, 0.09 mmol), 1,10-phenanthroline (67 mg, 0.2 eq, 0.37 mmol) and caesium carbonate (0.84 g, 1.4 eq, 2.6 mmol) were mixed in a RB flask, placed under vacuum and purged with N2 (g). 1-(4-Iodo-phenyl)-1H-pyrazole (0.5 g, 1.0 eq, 1.85 mmol), hydrazine carboxylic acid tert-butyl ester (0.3 g, 1.2 eq, 2.22 mmol) and DMF (25 ml) were added to the mixture which was then heated to 80° C. with stirring under an inert atmosphere for 21 hours. The reaction mixture was allowed to cool and was then filtered through a silica pad, which was then washed with ethyl acetate. The filtrate was then concentrated to dryness in vacuo. The resultant residue was purified by column chromatography using heptane/ethyl acetate (3:1) as eluent to yield impure title compound (0.42 g). LCMS: [M+H]+=275, rt=1.25 min, 48% purity.

Aufarbeitung

  1. custompurged with N2 (g)
  2. temperatureto cool
  3. filtrationwas then filtered through a silica pad, which
  4. washwas then washed with ethyl acetate
  5. concentrationThe filtrate was then concentrated to dryness in vacuo
  6. customThe resultant residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a6c1ae55b6d94996b6b07f9a0070461f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071607B2

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