Sodium Carbonate → Tert-butyl 2-(benzamido)-4-(3-(hydroxymethyl)phenyl)benzoate

HRID 1673460Notes

Reaction equation

HRID 1673460 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:18]([NH:26][C:27]1[CH:39]=[C:38](Br)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2)CCCCC1.CN(C)C(=O)C>[C:18]([NH:26][C:27]1[CH:39]=[C:38]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67343132Tert-butyl 2-(benzamido)-4-(3-(hydroxymethyl)phenyl)benzoate

Reagents, catalysts & solvents 2

HCID 86634613dicyclohexylphenylphosphine palladium(II)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

42 mg of 3-hydroxymethylphenylboronic 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 90° C. for 15 hours. After the reaction mixture was cooled do room temperature, 6 mg of polymer supported di(acetato) dicyclohexylphenylphosphine palladium(II) was added and stirred at 110° C. for 9 hours and 30 minutes. 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-(3-(hydroxymethyl)phenyl)benzoate.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. customdo room temperature
  3. additionwas added
  4. stirringstirred at 110° C. for 9 hours and 30 minutes
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. custominsoluble were removed by filtration and ethyl acetate and 10% citric acid aqueous solution
  7. additionwere added
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. washafter washed with 10% citric acid aqueous solution
  11. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  12. 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-c63228c9de1e441cb02729e2813d741e
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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