HCID 20746075, Verbindung → HCID 20746058, Verbindung

HRID 2308089

Reaktionsgleichung

Reaktionsgleichung von HRID 2308089
[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:17])=[O:4]>CCOC(C)=O.CCO.[Pd]>[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:17])=[O:4].[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH2:7][CH:6]1[CH3:17])=[O:4]

Komponenten

6

Edukt 1

HCID 20746075HCID 20746075, Verbindung

Produkt 2

HCID 207460575-Amino-2-methylindole-1-carboxylic acid methylamideAusbeute 24 %HCID 20746058HCID 20746058, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-methyl-5-nitro-indole-1-carboxylic acid methylamide (0.65 g, 2.78 mmol) in 20 mL EtOAc and 4 mL EtOH was added Pd on C (0.3 g, 10% w/w). The mixture was stirred under H2 balloon at room temperature for one hour and filtered through a pad of silica gel. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography eluting with 1-3% MeOH in CH2Cl2 to give 140 mg 5-amino-2-methyl-indole-1-carboxylic acid methylamide (24% yield) together with 150 mg 5-amino-2-methyl-2,3-dihydro-indole-1-carboxylic acid methylamide (26% yield). 1H NMR (300 MHz, CD3OD) δ 7.56 (d, 1H, J=6.2 Hz), 6.65 (s, 1H), 6.58 (d, 1H, J=6.1 Hz), 4.41 (m, 1H), 3.23-3.39 (m, 1H), 2.85 (s, 3H), 2.54 (d, 1H, J=15.5 Hz), 1.20 (d, 3H, J=6 Hz).

Aufarbeitung

  1. filtrationfiltered through a pad of silica gel
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography
  4. washeluting with 1-3% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-65353e0805584a0f92cb630574acc702
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06833456B2

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