Sodium Carbonate → HCID 57668040, compound

HRID 2191644Notes

Reaction equation

HRID 2191644 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.[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=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:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=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 2856454-Fluorophenylboronic acidHCID 57667801HCID 57667801, compound

Product 1

HCID 57668040HCID 57668040, compoundYield 11.1%

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 4-fluorophenylboronic acid 45 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, and 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. 1.0 mol/L Sodium hydroxide aqueous solution 1.0 mL and ethanol 3.0 mL were added to the obtained residue, and it was stirred at room temperature for 1 hour. 6.0 mol/L Hydrochloric acid was added to the reaction mixture, solid matter was filtrated, and it was refined by silica gel column chromatography [Trikonex company, Flash Tube,2008, eluent; hexane:ethyl acetate:acetic acid=20:10:1] to give 2-(4-fluoroanilino)-4-(4-fluorophenyl)benzoic acid 7.8 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. washafter sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure
  7. addition1.0 mol/L Sodium hydroxide aqueous solution 1.0 mL and ethanol 3.0 mL were added to the obtained residue, and it
  8. stirringwas stirred at room temperature for 1 hour
  9. addition6.0 mol/L Hydrochloric acid was added to the reaction mixture, solid matter
  10. filtrationwas filtrated

Sources & evidence

ORD record
ord-6b180fbe74d6465a95eef4c123bbffca
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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