Potassium Carbonate → 6-((8-bromo-7-(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)nicotinonitrile

HRID 2101303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101303
[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=1>CN(C=O)C.O>[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[N:16]([CH2:26][C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=3)[N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 149805356-(Chloromethyl)pyridine-3-carbonitrileHCID 577994388-Bromo-7-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Produkt 1

HCID 577993806-((8-bromo-7-(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)nicotinonitrileAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred mixture of 8-bromo-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (1.07 g, 3.31 mmol) in DMF (15 mL) at room temperature under argon was added K2CO3 (0.91 g, 6.62 mmol) and 6-(chloromethyl)nicotinonitrile (0.63 g, 4.14 mmol). The mixture was then heated to 60° C. for 7 h, after which HPLC indicated complete reaction. The mixture was cooled to room temperature, diluted with water (100 mL), and stirred for 30 min. Solid was collected by filtration and washed with water (10 mL×5), then methanol (3 mL×3), and finally dried under vacuum. The title compound (0.98 g) was obtained as a tan solid. HPLC/MS: retention time=3.4 min, [M+H]+=442.

Aufarbeitung

  1. customreaction
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationSolid was collected by filtration
  4. washwashed with water (10 mL×5)
  5. dry with materialmethanol (3 mL×3), and finally dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cc9e7a8e9d5a4230987b1e622ba8425a
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572808B2

Notizen zur Reaktion

Wird geladen…