Potassium Carbonate → HCID 86294663, Verbindung

HRID 2178107

Reaktionsgleichung

Reaktionsgleichung von HRID 2178107
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[Cl:21][C:22]1[CH:29]=[C:28]([OH:30])[CH:27]=[CH:26][C:23]=1[C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CS(C)=O.C(OCC)(=O)C>[Cl:21][C:22]1[CH:29]=[C:28]([CH:27]=[CH:26][C:23]=1[C:24]#[N:25])[O:30][C:8]1[CH:7]=[CH:6][C:5]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)(=[O:12])=[O:11])=[CH:4][C:3]=1[C:1]#[N:2]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 594366003-cyano-4-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide

Produkt 1

HCID 86294663HCID 86294663, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Cyano-4-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 2, 10.5 g, 35.6 mmol) was added to a solution of 2-chloro-4-hydroxybenzonitrile (8.19 g, 53.3 mmol) and potassium carbonate (14.74 g, 106.7 mmol) in dimethylsulfoxide (100 mL) at room temperature. The resulting mixture was stirred at 80° C. for 44 hours. On cooling, the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution (200 mL) and ethyl acetate (1000 mL) was added. The aqueous layer was separated and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (3×200 mL), water (2×200 mL) and brine (2×200 mL). The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by reverse phase column chromatography eluting with acetonitrile (containing 0.1% HCO2H): water (containing 0.1% HCO2H) from 0 to 100% to afford the title compound as a white solid (6.982 g, 46%).

Aufarbeitung

  1. temperatureOn cooling
  2. additionwas added
  3. customThe aqueous layer was separated
  4. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (3×200 mL), water (2×200 mL) and brine (2×200 mL)
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by reverse phase column chromatography
  9. washeluting with acetonitrile (containing 0.1% HCO2H)

Quellen und Nachweise

ORD-Eintrag
ord-be6b74a1d1394616becd589715437aba
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067922B2

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