Potassium Carbonate → HCID 86685263, Verbindung

HRID 402758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402758
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[C:9]([CH:14]=[O:15])=[N:10][N:11]([CH3:13])[CH:12]=1.[F:16][C:17]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])O.[Na+]>CCO.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][N:11]1[CH:12]=[C:8]([C:20]2[CH:19]=[CH:18][C:17]([F:16])=[C:22]([F:23])[C:21]=2[F:24])[C:9]([CH:14]=[O:15])=[N:10]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27355954-bromo-1-methyl-1H-pyrazole-3-carbaldehydeHCID 27832802,3,4-Trifluorobenzeneboronic acid

Produkt 1

HCID 86685263HCID 86685263, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Potassium carbonate (0.418 mL, 0.836 mmol), Pd(OAc)2 (2.82 mg, 0.013 mmol) was added to a stirred, room temperature mixture of 4-bromo-1-methyl-1H-pyrazole-3-carbaldehyde (79 mg, 0.418 mmol) and (2,3,4-trifluorophenyl)boronic acid (96 mg, 0.543 mmol) in EtOH (0.7 mL) and the mixture was stirred at 90° C. for 24 hours. The mixture was cooled, aqueous sodium hydrogen carbonate (saturated, 10 mL) was added and the mixture was extracted with ethyl acetate (2×15 mL). The combined organic fractions were washed with water, dried (MgSO4) and filtered. The solvent was evaporated under reduced pressure to give the crude intermediate which was used in the next step.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate (2×15 mL)
  3. washThe combined organic fractions were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-23329ba69ccb41e29264933d269a1e57
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742110B2

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