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Oxonium, triethyl-, hexafluorophosphate(1-) (1:1) → methyl 5-bromo-2-ethyl-2H-indazole-4-carboxylate

HRID 1639769
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1639769
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][N:6]=[CH:5][C:4]=2[C:3]=1[C:11]([O:13][CH3:14])=[O:12].F[P-](F)(F)(F)(F)F.[CH2:22]([O+](CC)CC)[CH3:23]>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:22][CH3:23])[N:7]=2)[C:3]=1[C:11]([O:13][CH3:14])=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 167684Oxonium, triethyl-, hexafluorophosphate(1-) (1:1)HCID 59145907Methyl 5-bromo-1H-indazole-4-carboxylate

Produkt 1

HCID 59334535methyl 5-bromo-2-ethyl-2H-indazole-4-carboxylateAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittel2×HCID 516892
Sodium Bicarbonate
Lösungsmittel

Versuchsvorschrift

To a solution of methyl 5-bromo-1H-indazole-4-carboxylate (2.00 g, 7.84 mmol) in ethyl acetate (80 mL) was added triethyloxonium hexafluorophosphate (2.92 g, 11.8 mmol), and the mixture was stirred under nitrogen atmosphere at room temperature for 15 hr. The reaction solution was diluted with ethyl acetate, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=5/95→50/50) to give the title compound (2.03 g, yield 91%).

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=5/95→50/50)

Quellen und Nachweise

ORD-Eintrag
ord-8e04857c7a53444f9c0009e3ecc11411
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08110585B2

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