Sodium Carbonate → 1-Benzenesulfonyl-4-(5'-fluoro-2'-methyl-biphenyl-3-yl)-3-isopropyl-imidazolidin-2-one

HRID 560103Notes

Reaction equation

HRID 560103 reaction equation
[C:1]1([S:7]([N:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=3)[N:12]([CH:22]([CH3:24])[CH3:23])[C:11]2=[O:25])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:36])=[C:31](B(O)O)[CH:32]=1.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:16]=[C:17]([C:29]4[CH:28]=[C:27]([F:26])[CH:32]=[CH:31][C:30]=4[CH3:36])[CH:18]=[CH:19][CH:20]=3)[N:12]([CH:22]([CH3:24])[CH3:23])[C:11]2=[O:25])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27831905-Fluoro-2-methylphenylboronic acidHCID 670010961-Benzenesulfonyl-4-(3-bromo-phenyl)-3-isopropyl-imidazolidin-2-one

Product 1

HCID 445482071-Benzenesulfonyl-4-(5'-fluoro-2'-methyl-biphenyl-3-yl)-3-isopropyl-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-(3-bromo-phenyl)-3-isopropyl-imidazolidin-2-one (example 12, step 1) was reacted with 5-fluoro-2-methylphenylboronic 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-(5′-fluoro-2′-methyl-biphenyl-3-yl)-3-isopropyl-imidazolidin-2-one as a light yellow oil. MS: 453.1 ([M+H]+)

Sources & evidence

ORD record
ord-90ad009a03d842c5883d9c7f3cae5030
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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