Potassium Carbonate → Ethyl 2-(2-(4-cyanophenyl)pyridin-3-ylthio)-2-methylpropanoate

HRID 470377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470377
[SH:1][C:2]1[C:3]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Br[C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([C:3]2[C:2]([S:1][C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:9][CH:10]=1)#[N:13]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 679970364-(3-Mercaptopyridin-2-yl)benzonitrile

Produkt 1

HCID 67997044Ethyl 2-(2-(4-cyanophenyl)pyridin-3-ylthio)-2-methylpropanoateAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-mercaptopyridin-2-yl)benzonitrile (0.18 g, 0.85 mmol), ethyl 2-bromo-2-methylpropanoate (0.195 g, 1 mmol), and K2CO3 (0.138 g, 1.0 mmol) in DMF (2 mL) was stirred at room temperature for 2 hours. After the reaction was completed, the reaction mixture was washed with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated and purified by chromatography to yield ethyl 2-(2-(4-cyanophenyl)pyridin-3-ylthio)-2-methylpropanoate (0.137 g, 49%).

Aufarbeitung

  1. washthe reaction mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2c22b5c0be4c493aa38d3515d1651b24
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629278B2

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