Sodium Carbonate → HCID 67342183, compound

HRID 1673371Notes

Reaction equation

HRID 1673371 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[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:20]([NH:28][C:29]1[CH:38]=[C:37]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[CH:36]=[CH:35][C:30]=1[C:31]([OH:33])=[O:32])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67342183HCID 67342183, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

56 mg of (4-(tert-butyl)phenyl)boronic acid, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetate)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 21 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.0 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 she solvent was evaporated under reduced pressure. 1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 5.0 mL of ethanol were added to the obtained residue and stirred at room temperature for 1 hour and 30 minutes. 0.5 mol/L hydrochloric acid and ethyl acetate were added to the reaction mixture. The organic layer was separated and the solvent was evaporated under reduced pressure to obtain 9.3 mg of 2-(benzamido)-4-(4-(tert-butyl)phenyl)benzoic acid as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. custominsoluble were removed by filtration and ethyl acetate and 1.0 mol/L hydrochloric acid
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with 1.0 mol/L hydrochloric acid
  7. customa saturated sodium chloride aqueous solution sequentially, and she solvent was evaporated under reduced pressure
  8. addition1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 5.0 mL of ethanol were added to the obtained residue
  9. stirringstirred at room temperature for 1 hour and 30 minutes
  10. addition0.5 mol/L hydrochloric acid and ethyl acetate were added to the reaction mixture
  11. customThe organic layer was separated
  12. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ae0c3a52e9aa4c34acdff11e6bcb5736
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

Loading…