Potassium Carbonate → 1-[6-(4-Methyl-1H-imidazol-1-yl)pyridin-3-yl]ethan-1-one

HRID 505575

Reaktionsgleichung

Reaktionsgleichung von HRID 505575
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:11][C:12]1[N:13]=[CH:14][N:15]([C:2]2[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH:16]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 178418800HCID 178418800, Verbindung

Produkt 1

HCID 450967261-[6-(4-Methyl-1H-imidazol-1-yl)pyridin-3-yl]ethan-1-oneAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

1-(6-chloro-pyridin-3-yl)-ethanone (7.00 g, 45.16 mmol) and 4-methylimidazole (11.11 g, 135.50 mmol) were combined in DMSO (35 ml), before addition of K2CO3. The mixture was heated at 110° C. for 22 h with rapid stirring. The reaction was then cooled to room temperature and poured into ice water (400 ml) with vigorous stirring for 15 min. The resulting precipitate was collected on a filter and washed generously with water. The resulting material was dried in vacuo to yield 19 as a tan solid (6.1 g, 67%). LC/MS: [M+1]+=202.2. C11H11N3O=201.2. 1H NMR (DMSO-d6) 300 MHz δ2.18 (3H, s), 2.63 (3H, s), 7.72 (1H, s), 7.87 (2H, d: J=9.0 Hz), 8.41 (2H, d, J=9.0 Hz), 8.51 (1H, s), 8.98 (1H, s).

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. customThe resulting precipitate was collected on
  3. filtrationa filter
  4. washwashed generously with water
  5. customThe resulting material was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a7fd66f93a10462ea08814954004a22f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781442B2

Verknüpfte Notizen

Wird geladen…