Sodium Carbonate → HCID 57879490, compound

HRID 1673374Notes

Reaction equation

HRID 1673374 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[C:18]([NH:26][C:27]1[CH:36]=[C:35](Br)[CH:34]=[CH:33][C:28]=1[C:29]([O:31]C)=[O:30])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C(=O)C>[C:18]([NH:26][C:27]1[CH:36]=[C:35]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:34]=[CH:33][C:28]=1[C:29]([OH:31])=[O:30])(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 57879490HCID 57879490, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

56 mg of 2,4-difluorophenylboronic acid, 63 mg of sodium carbonate and 34 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 80 mg of methyl 2-(benzamido)-4-bromobenzoate, and starred at 90° C. for 20 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.2 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 1.0 mL of 1.0 mol/L aqueous sodium hydroxide and 4.0 mL of ethanol were added to the obtained residue and stirred at room temperature for 1 hour. 0.6 mol/L hydrochloric acid, was added to the reaction mixture and a solid substance was separated by filtration to obtain 24 mg of 2-(benzamido)-4-(2,4-difluorophenyl)benzoic acid.

Workup

  1. custominsoluble were removed by filtration and ethyl acetate and 1.2 mol/L hydrochloric acid
  2. additionwere added
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with 1.0 mol/L hydrochloric acid
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  7. addition1.0 mL of 1.0 mol/L aqueous sodium hydroxide and 4.0 mL of ethanol were added to the obtained residue
  8. addition0.6 mol/L hydrochloric acid, was added to the reaction mixture
  9. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-9baafd450e5940d2a59f9529367b4d3a
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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