Potassium Carbonate → HCID 50997448, compound

HRID 1807377Notes

Reaction equation

HRID 1807377 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:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[Cl:31].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:26]=[C:27]([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:28]=[CH:29][C:30]=1[Cl:31]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343303,4-Dichlorobenzeneboronic acidHCID 50997446HCID 50997446, compound

Product 1

HCID 50997448HCID 50997448, compoundYield 60%

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, 3,4-dichloro-phenyl boronic acid (0.096 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 0.12 g (60% of theory) of 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-(3′,4′-dichloro-biphenyl-3-yl)-ethyl]-methoxy-amide in form of a solid. Mp 162-164° C.

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-95fc2081226944db9bcf77998e4547ad
Source dataset
uspto-grants-2013_01
Patent number
US08357634B2

Reaction notes

Loading…