Sodium Carbonate → 4'-(1-Benzenesulfonyl-2-oxo-3-phenyl-imidazolidin-4-yl)-biphenyl-4-carboxylic acid

HRID 560084Notes

Reaction equation

HRID 560084 reaction equation
[C:1]1([S:7]([N:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=3)[N:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:11]2=[O:28])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)([OH:31])=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[C:1]1([S:7]([N:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([C:35]4[CH:36]=[CH:37][C:32]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=4)=[CH:17][CH:16]=3)[N:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:11]2=[O:28])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 670012201-Benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imidazolidin-2-one

Product 1

HCID 445475894'-(1-Benzenesulfonyl-2-oxo-3-phenyl-imidazolidin-4-yl)-biphenyl-4-carboxylic acidYield 33%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imidazolidin-2-one (100 mg) and 4-carboxyphenylboronic acid (57 mg) in dioxane (0.6 mL) and water (0.4 mL) under argon were added a 2 M aqueous sodium carbonate solution (0.33 mL) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (9 mg). The mixture was stirred at 80° C. for 3 h. After cooling to room temperature, the mixture was filtered. The filtrate was diluted with ethyl acetate and washed with 10% aqueous KHSO4 solution. The org. phase was dried (MgSO4), filtered and concentrated. The product was purified using column chromatography (SiO2, dichloromethane/methanol 1:0=>4:1) to give 4′-(1-benzenesulfonyl-2-oxo-3-phenyl-imidazolidin-4-yl)-biphenyl-4-carboxylic acid (36 mg) as an off-white solid. MS: 497.1 ([M−H]−)

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with 10% aqueous KHSO4 solution
  5. dry with materialphase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified

Sources & evidence

ORD record
ord-aa845280ffe2477dbe9facb277cf885c
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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