Potassium Cyanide → (1-[(tert-butoxycarbonyl)oxy]-6-methoxy-1H-indazol-3-yl)acetonitrile

HRID 1921262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921262
[C-:1]#[N:2].[K+].[C:4]([O:8][C:9]([O:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([CH2:23]Br)=[N:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C(O)C>[C:4]([O:8][C:9]([O:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([CH2:23][C:1]#[N:2])=[N:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Komponenten

5

Edukt 2

HCID 9032Potassium CyanideHCID 231171601-[(tert-butoxycarbonyl)oxy]-6-methoxy-3-bromomethyl-1H-indazole

Produkt 1

HCID 23117149(1-[(tert-butoxycarbonyl)oxy]-6-methoxy-1H-indazol-3-yl)acetonitrileAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

KCN (5.73 g, 88 mmol) in 23 ml of H2O was added dropwise at 0° C. to 1-[(tert-butoxycarbonyl)oxy]-6-methoxy-3-bromomethyl-1H-indazole (10.5 g, 30.08 mmol) in 80 ml of ethanol and stirred at room temperature for 1 h30. The mixture was poured into water, and extracted with ethyl acetate. The organic layer was dried over Na2SO4. Concentration and precipitation in diisopropyl ether gave the expected product (4.42 g, 50% as solid).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationConcentration and precipitation in diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-970586ed9c1e4deca489af392aab1d60
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173679B2

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