Sodium Carbonate → Tert-butyl 2-(benzamido)-4-(4-phenoxyphenyl)benzoate

HRID 1673462Notes

Reaction equation

HRID 1673462 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:23]([NH:31][C:32]1[CH:44]=[C:43](Br)[CH:42]=[CH:41][C:33]=1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2)CCCCC1.CN(C)C(=O)C>[C:23]([NH:31][C:32]1[CH:44]=[C:43]([C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH:42]=[CH:41][C:33]=1[C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343774-Phenoxyphenylboronic acidHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67341966Tert-butyl 2-(benzamido)-4-(4-phenoxyphenyl)benzoate

Reagents, catalysts & solvents 2

HCID 86634613dicyclohexylphenylphosphine palladium(II)Catalyst2×HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

60 mg of 4-phenoxyphenylboronic acid, 49 mg of sodium carbonate and 6 mg of polymer supported di(acetato) dicyclohexylphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate, and stirred at: 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, 6 mg of polymer supported di(acetato) dicyclohexylphenylphosphine palladium(II) was added and stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex company, eluent; hexane: ethyl acetate=4:1] to obtain tert-butyl 2-(benzamido)-4-(4-phenoxyphenyl)benzoate.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. additionwas added
  3. stirringstirred at 110° C. for 24 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. custominsoluble were removed by filtration and ethyl acetate and 10% citric acid aqueous solution
  6. additionwere added
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter washed with 10% citric acid aqueous solution
  10. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex company, eluent; hexane: ethyl acetate=4:1]

Sources & evidence

ORD record
ord-a411bd86c0a241468335082f2f11aead
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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