Potassium Carbonate → 3-(2-Butynyl)-4-chloro-3H-imidazo[4,5-c]pyridine

HRID 501436

Reaktionsgleichung

Reaktionsgleichung von HRID 501436
[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.Br[CH2:12][C:13]#[C:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:12]([N:8]1[C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=[CH:9]1)[C:13]#[C:14][CH3:15]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 53733644-Chloro-1H-imidazo[4,5-c]pyridine

Produkt 1

HCID 230707293-(2-Butynyl)-4-chloro-3H-imidazo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.0 μg of 4-chloro-1H-imidazo[4,5-c]pyridine, 1.37 ml of 1-bromo-2-butyne, and 1.98 g of potassium carbonate were suspended in 15 ml of N,N-dimethylformamide, and the suspension was stirred at room temperature for 18 hours. The reaction solution was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 1.79 g of a 1:1 mixture consisting of the title compound and the compound alkylated at the 1-position was obtained from the fraction eluted with hexane-ethyl acetate (1:2).

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customwas obtained from the fraction
  7. washeluted with hexane-ethyl acetate (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-4e79662faa7b4275ba4d474640fe3eaf
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772226B2

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