Potassium Carbonate → HCID 50997447, compound

HRID 1807376Notes

Reaction equation

HRID 1807376 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]([N:10]([O:22][CH3:23])[C:11]([C:13]2[C:14]([CH:19]([F:21])[F:20])=[N:15][N:16]([CH3:18])[CH:17]=2)=[O:12])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([N:10]([O:22][CH3:23])[C:11]([C:13]3[C:14]([CH:19]([F:21])[F:20])=[N:15][N:16]([CH3:18])[CH:17]=3)=[O:12])[CH3:9])[CH:3]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 50997446HCID 50997446, compound

Product 1

HCID 50997447HCID 50997447, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-(3-iodo-phenyl)-ethyl]-methoxy-amide (0.2 g, 0.46 mmol), prepared as described in example P2, in a mixture of ethanol (12 ml) and water (4 ml) was added, 4-chloro-phenyl boronic acid (0.079 g, 0.5 mmol) followed by palladium acetate (0.052 g, 0.23 mmol) and potassium carbonate (0.19 g, 1.38 mmol). It was stirred for 18 hours at ambient temperature. Reaction mass was filtered on celite bed then diluted with water and extracted in ethyl acetate (3×60 ml), washed with water, brine and dried over anhydrous sodium sulfate. The crude mass was purified by column chromatography using 36% Ethyl acetate in hexane to yield 0.09 g (50% of theory) of 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-(4′ chloro-biphenyl-3-yl)-ethyl]-methoxy-amide in form of a resin.

Workup

  1. additionwas added
  2. customReaction mass
  3. filtrationwas filtered on celite bed
  4. additionthen diluted with water
  5. extractionextracted in ethyl acetate (3×60 ml)
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe crude mass was purified by column chromatography

Sources & evidence

ORD record
ord-c09af6d14c7c44b8a6cae6001672c26f
Source dataset
uspto-grants-2013_01
Patent number
US08357634B2

Reaction notes

Loading…