Benzo(B)Thiophene-2-Boronic Acid → HCID 57879571, compound

HRID 1673372Notes

Reaction equation

HRID 1673372 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[C:19]([NH:27][C:28]1[CH:37]=[C:36](Br)[CH:35]=[CH:34][C:29]=1[C:30]([O:32]C)=[O:31])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C(=O)C>[C:19]([NH:27][C:28]1[CH:37]=[C:36]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[CH:35]=[CH:34][C:29]=1[C:30]([OH:32])=[O:31])(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic Acid2×HCID 10340Sodium Carbonate2×HCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 57879571HCID 57879571, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

56 mg of benzothiophene-2-boronic acid, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) 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 12 hours. After cooled to room temperature 37 mg of benzothiophene-2-boronic acid and 22 mg of sodium carbonate were added and stirred at 90° C. for 12 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 the solvent was evaporated under reduced pressure. 1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 2.0 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 2.5 mg of 2-(benzamido)-4-(benzothiophen-2-yl)benzoic acid as white solid.

Workup

  1. additionwere added
  2. stirringstirred at 90° C. for 12 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. custominsoluble were removed by filtration and ethyl acetate and 1.0 mol/L hydrochloric acid
  5. additionwere added
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. washafter washed with 1.0 mol/L hydrochloric acid
  9. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  10. addition1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 2.0 mL of ethanol were added to the obtained residue
  11. stirringstirred at room temperature for 1 hour
  12. addition0.6 mol/L hydrochloric acid was added to the reaction mixture
  13. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-cc1602fd018148b085e316607ca7bf07
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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