tert-Butyl 7-nitro-1H-indazole-1-carboxylate → tert-Butyl 7-amino-1H-indazole-1-carboxylate

HRID 482344

Reaktionsgleichung

Reaktionsgleichung von HRID 482344
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:10]=[CH:9]2)([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:10]=[CH:9]2

Komponenten

4

Edukt 1

HCID 15606021tert-Butyl 7-nitro-1H-indazole-1-carboxylate

Produkt 1

HCID 19063674tert-Butyl 7-amino-1H-indazole-1-carboxylateAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 7-Nitro-1-tert-butoxycarbonyl-indazole (1.000 g, 3.798 mmol), prepared as in Intermediate 25, and palladium on carbon (10 wt %, 0.10 g) in ethyl acetate (25 mL) at ambient temperature is stirred under atmospheric hydrogen overnight. The mixture is filtered through celite and concentrated in vacuo to an oil which solidified under high vacuum to provide the title compound as a purple solid (0.860 g, 3.686 mmol). 1H NMR (300 MHz, d6-DMSO) δ=1.59 (b, 9H); 6.13 (b, 2H); 6.76 (d, J=7.6 Hz, 1H); 6.97 (d, J=7.6 Hz, 1H); 7.04-7.07 (m, 1H); 8.24 (s, 1H). TLC: Rf =0.47 (25:75 ethyl acetate: n-hexane).

Aufarbeitung

  1. filtrationThe mixture is filtered through celite and
  2. concentrationconcentrated in vacuo to an oil which

Quellen und Nachweise

ORD-Eintrag
ord-1c98404b27ed402791ff60fcc610f772
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795887

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