Potassium Carbonate → HCID 86685263, compound

HRID 402758Notes

Reaction equation

HRID 402758 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 86685263HCID 86685263, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-23329ba69ccb41e29264933d269a1e57
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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