HCID 22036770, Verbindung → tert-Butyl 6-amino-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 1764816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1764816
[N+:1]([C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 1

HCID 22036770HCID 22036770, Verbindung

Produkt 1

HCID 22036788tert-Butyl 6-amino-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (15.6 g, 49.15 mmol) in ethanol (250 mL) was added a spatula tip of 10% Pd/C. The reaction mixture was shaken under a hydrogen atmosphere (15 psi, Parr apparatus) for 2 h. Upon removal from the Parr apparatus, the reaction mixture was filtered through Celite. The Celite was washed with ethanol and the combined filtrates were concentrated in vacuo to give tert-butyl 6-amino-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate, quantitatively as a white solid: 1H NMR (CDCl3, 500 MHz) δ 1.42-1.67 (m, 9H), 2.74-2.85 (m, 2H), 3.58 (brs, 2H), 3.79 (brs, 2H), 4.60 (brs, 2H), 6.53-6.56 (m, 1H), 6.89-6.99 (m, 2H), 7.77 (brs, 1H) ppm.

Aufarbeitung

  1. customUpon removal from the Parr apparatus
  2. filtrationthe reaction mixture was filtered through Celite
  3. washThe Celite was washed with ethanol
  4. concentrationthe combined filtrates were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-adef43a454cc44c989eef71196663bed
Quelldatensatz
uspto-grants-2007_06
Patentnummer
USRE039680E1

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