Reaktion #647288

ord-ed4a196afb274e9eac278dfd0ac6aa61

Reaktionsgleichung

CC(C)N1C(=O)N(S(=O)(=O)c2ccccc2)CC1c1cccc(Br)c1
3,1-benzenesulfonyl-4-(3-bromo-phenyl)-3-isopropyl-imidazolidin-2-one
CC(C)N1C(=O)N(S(=O)(=O)c2ccccc2)CC1c1cccc(Br)c1
1-benzenesulfonyl-4-(3-bromo-phenyl)-3-isopropyl-imidazolidin-2-one
OB(O)c1cc(F)ccc1Cl
2-chloro-5-fluorophenylboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
CC(C)N1C(=O)N(S(=O)(=O)c2ccccc2)CC1c1cccc(-c2cc(F)ccc2Cl)c1
1-benzenesulfonyl-4-(2′-chloro-5′-fluoro-biphenyl-3-yl)-3-isopropyl-imidazolidin-2-one

Edukte

CC(C)N1C(=O)N(S(=O)(=O)c2ccccc2)CC1c1cccc(Br)c1
3,1-benzenesulfonyl-4-(3-bromo-phenyl)-3-isopropyl-imidazolidin-2-one
CC(C)N1C(=O)N(S(=O)(=O)c2ccccc2)CC1c1cccc(Br)c1
1-benzenesulfonyl-4-(3-bromo-phenyl)-3-isopropyl-imidazolidin-2-one
OB(O)c1cc(F)ccc1Cl
2-chloro-5-fluorophenylboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Reagenzien

ClCCl.[Cl][Pd][Cl].[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1
dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane

Lösungsmittel

C1COCCO1.O
dioxane water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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 2-chloro-5-fluorophenylboronic 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′-chloro-5′-fluoro-biphenyl-3-yl)-3-isopropyl-imidazolidin-2-one as a light yellow oil. MS: 472.9 ([M+H]+)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08063088B2uspto-grants-2011_11