Sodium Carbonate → 4-(4-(Acetamido)phenyl)-2-(benzamido)benzoic acid

HRID 1673367Notes

Reaction equation

HRID 1673367 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[C:20]([NH:28][C:29]1[CH:38]=[C:37](Br)[CH:36]=[CH:35][C:30]=1[C:31]([O:33]C)=[O:32])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:37]2[CH:36]=[CH:35][C:30]([C:31]([OH:33])=[O:32])=[C:29]([NH:28][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:38]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 27346574-Acetamidophenylboronic acid2×HCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 578793804-(4-(Acetamido)phenyl)-2-(benzamido)benzoic acidYield 7.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

56 mg of 4-(acetamido)phenylboronic acid, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(11) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of methyl 2-(benzamido)-4-bromobenzoate, and stirred at 90° C. for 11 hours. After the reaction mixture was cooled to room temperature, 19 mg of 4-(acetamido)phenylboronic acid was added and the mixture was stirred at 90° C. for 12 hours. After the reaction mixture was cooled to room temperature, 11 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added and stirred at 90° C. for 14 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, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 1 mL of 1.0 mol/L aqueous sodium hydroxide and 2 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, and solid substances were separated by filtration and purified with reversed-phase silica gel column chromatography [eluent; 40-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 5.9 mg of 4-(4-(acetamido)phenyl)-2-(benzamido)benzoic acid as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at 90° C. for 12 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. additionwere added
  5. stirringstirred at 90° C. for 14 hours
  6. temperatureAfter the reaction mixture was cooled to room temperature
  7. custominsoluble were removed by filtration and ethyl acetate and 1.2 mol/L hydrochloric acid
  8. additionwere added
  9. customThe organic layer was separated
  10. dry with materialdried over anhydrous magnesium sulfate
  11. washafter washed with 1.0 mol/L hydrochloric acid
  12. customa saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  13. addition1 mL of 1.0 mol/L aqueous sodium hydroxide and 2 mL of ethanol were added to the obtained residue
  14. stirringstirred at room temperature for 1 hour
  15. addition0.6 mol/L hydrochloric acid was added
  16. customsolid substances were separated by filtration
  17. custompurified with reversed-phase silica gel column chromatography [eluent; 40-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record
ord-a08728bace274357b05bb58894188b7b
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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