Ethanol → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 1014718

Reaktionsgleichung

Reaktionsgleichung von HRID 1014718
[C:1]1([CH:7]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][CH:21]=[N:22]4)[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](C1C(NC(C2C=CC=CC=2)C)=NC(C2C=CC=C3C=2C=CC=N3)=CC=1)([O-])=O.[CH2:55]([OH:57])C>[Pd]>[C:1]1([CH:7]([N:9]2[C:10]3=[N:11][C:12]([C:17]4[CH:26]=[CH:25][CH:24]=[C:23]5[C:18]=4[CH:19]=[CH:20][CH:21]=[N:22]5)=[CH:13][CH:14]=[C:15]3[NH:16][C:55]2=[O:57])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 666998813-Nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amineHCID 77571172N2-(1-Phenylethyl)-6-(quinolin-5-yl)pyridine-2,3-diamine

Produkt 1

HCID 249846803-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

N2-(1-Phenylethyl)-6-(quinolin-5-yl)pyridine-2,3-diamine. A solution of 3-nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amine (2.36 g, 6.37 mmol) in ethanol (175 mL) was purged with nitrogen for several min. Following addition of palladium on carbon (245 mg, 2.29 mmol), the flask was evacuated and a hydrogen filled balloon was placed on the reaction. After stirring at room temperature for 18 h, the reaction was filtered and the solvent removed under reduced pressure to afford the title compound (1.89 g, 87% yield). MS (ESI) m/z 341.3 [M+1]+.

Aufarbeitung

  1. customthe flask was evacuated
  2. customa hydrogen filled balloon was placed on the reaction
  3. filtrationthe reaction was filtered
  4. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a9700c1b17984d36965424bb03d1372d
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981893B2

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