t-Butyl 5-nitroindole-2-carboxylate → Tert-butyl 5-amino-1H-indole-2-carboxylate

HRID 1456880

Reaktionsgleichung

Reaktionsgleichung von HRID 1456880
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7]2)([O-])=O>C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7]2

Komponenten

3

Edukt 1

HCID 10801431t-Butyl 5-nitroindole-2-carboxylate

Produkt 1

HCID 10633339Tert-butyl 5-amino-1H-indole-2-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A flask was charged with 9 (3.5 g, 13.3 mmol) and 100 mL dry THF, and purged with argon. To this solution was then added palladium hydrogenation catalyst (10% on carbon, 0.6 g) and hydrogen was bubbled into the reaction mixture for 2.5 days. The catalyst was removed by filtration and the solvent was evaporated to give 10 (2.8 g, 91% yield) as a brown solid: NMR (acetone-d6) δ1.6 (s, 9H), δ6.6-7.6 (m, 4H).

Aufarbeitung

  1. custompurged with argon
  2. customadded palladium hydrogenation catalyst (10% on carbon, 0.6 g) and hydrogen was bubbled into the reaction mixture for 2.5 days
  3. customThe catalyst was removed by filtration
  4. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-883419c8913748ce81a496bb67ba7eea
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05846545

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