Sodium Carbonate → HCID 57668027, compound

HRID 2191643Notes

Reaction equation

HRID 2191643 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:4]2[CH:3]=[C:2]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([O:21][CH3:20])[CH:27]=3)[CH:11]=[CH:10][C:5]=2[C:6]([OH:8])=[O:7])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 57667801HCID 57667801, compound

Product 1

HCID 57668027HCID 57668027, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

To N,N-dimethylacetamide 2.5 mL solution of methyl 4-bromo-2-(4-fluoroanilino)benzoate 70 mg were added 3-methoxyphenylboronic acid 49 mg, sodium carbonate 57 mg and polymer-carried bis(acetato)triphenylphosphine palladium (II) 31 mg at room temperature, and it was stirred at 90° C. for 12 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. To the obtained residue were added 2.0 mol/L sodium hydroxide aqueous solution 1.0 mL and ethanol 6.0 mL, and it was stirred at room temperature for 1 hour. 0.5 mol/L Hydrochloric acid was added to the reaction mixture, solid matter was filtrated to give 2-(4-fluoroanilino)-4-(3-methoxyphenyl)benzoic acid 10 mg of pale yellow solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationinsoluble matter was filtrated
  3. additionethyl acetate and 1.0 mol/L hydrochloric acid were added to it
  4. customThe organic layer was separated
  5. customcollected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure
  9. additionTo the obtained residue were added 2.0 mol/L sodium hydroxide aqueous solution 1.0 mL and ethanol 6.0 mL, and it
  10. stirringwas stirred at room temperature for 1 hour
  11. addition0.5 mol/L Hydrochloric acid was added to the reaction mixture, solid matter
  12. filtrationwas filtrated

Sources & evidence

ORD record
ord-ecb07c7b87e84935b9bf99beffe9aed9
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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