Tetrabutylammonium Fluoride → tert-Butyl 5-hydroxy-3-iodo-1H-indazole-1-carboxylate

HRID 246719

Reaktionsgleichung

Reaktionsgleichung von HRID 246719
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:13]=[C:12]2[I:25])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[N:13]=[C:12]2[I:25]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 71279782HCID 71279782, Verbindung

Produkt 1

HCID 71280823tert-Butyl 5-hydroxy-3-iodo-1H-indazole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of tert-butyl 5-(tert-butyldimethylsilyloxy)-3-iodo-1H-indazole-1-carboxylate (1 g, 2.11 mmol) in THF (10 mL), was added TBAF (5.6 g, 21.1 mmol) in THF (5 mL). The mixture was stirred at room temperature for 0.5 hour. The solvent was removed under reduced pressure. The residue was diluted with water and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was used in the next step without purification. LCMS: 361 [M+H]+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was used in the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-8d543d0f60504360a6a41e959910119b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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