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Water → 1H-Indazole

HRID 1821418
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1821418
COCCN1CCN(C2C=CC(C=O)=C([N+]([O-])=O)C=2)CC1.[Br-].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:24]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[N:24]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 866282164-[4-(2-Methoxyethyl)piperazin-1-yl]-2-nitrobenzaldehydeHCID 178419401HCID 178419401, Verbindung

Produkt 1

HCID 92211H-IndazoleAusbeute 597,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A solution of 4-[4-(2-methoxyethyl)piperazin-1-yl]-2-nitrobenzaldehyde (0.23 g, 0.68 mmol) obtained in Step 1 was dissolved in methanol (8.0 mL) and the solution was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.32 g, 0.68 mmol) and potassium carbonate (0.19 g, 1.4 mmol), followed by stirring at room temperature for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain (E)-3-{2-[4-(2-methoxyethyl)piperazin-1-yl]-2-nitrophenyl}vinyl}-1H-indazole (0.48 g, 100%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1f935d76bff34ce4a68cc5c01c608219
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07605272B2

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