Sodium Carbonate → 1-Benzenesulfonyl-4-(2',5'-dimethyl-biphenyl 4-yl)-3-phenyl-imidazolidin-2-one

HRID 560086Notes

Reaction equation

HRID 560086 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.[CH3:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][C:31]=1B(O)O.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:31]4[CH:32]=[C:33]([CH3:36])[CH:34]=[CH:35][C:30]=4[CH3:29])=[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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734347(2,5-Dimethylphenyl)boronic acidHCID 670012201-Benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imidazolidin-2-one

Product 1

HCID 445475911-Benzenesulfonyl-4-(2',5'-dimethyl-biphenyl 4-yl)-3-phenyl-imidazolidin-2-one

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to example 1, step 3,1-benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imlidazolidin-2-one (example 1, step 2) was reacted with 2,5-dimethylphenylboronic acid in the presence of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct and sodium carbonate in dioxane/water to give 1-benzenesulfonyl-4-(2′,5′-dimethyl-biphenyl 4-yl)-3-phenyl-imidazolidin-2-one as a colorless solid. MS: 483.2 ([M+H]+)

Sources & evidence

ORD record
ord-c60e8d07a3d74951875ac3068e4b08f2
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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