tetra-(n-butyl)ammonium iodide; potassium carbonate in N,N-dimethyl-formamide T=60°C; 17 h;

1: (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one With sodium hexamethyldisilazane in N,N-dimethyl-formamide T=-15°C; 1.5 h; 2: 2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl in N,N-dimethyl-formamide T=-15 - 12°C;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol; water; benzene T=100°C; 14 h; Heating / reflux;

1.1: tetrahydrofuran / 1 h / -15 - 0 °C 2.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr 3.1: N-bromosuccinmide / acetonitrile / 35 °C 4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 24 h / 35 °C / Inert atmosphere 6.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C 7.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 7.2: -15 - 12 °C View Scheme

1.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr 2.1: N-bromosuccinmide / acetonitrile / 35 °C 3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 24 h / 35 °C / Inert atmosphere 5.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C 6.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 6.2: -15 - 12 °C View Scheme

1.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 24 h / 35 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C 3.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 3.2: -15 - 12 °C View Scheme

1.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 24 h / 35 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C 4.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 4.2: -15 - 12 °C View Scheme

1.1: tetrahydrofuran / 5 h / 65 - 68 °C 2.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1 h / -10 - 5 °C 3.1: tetrahydrofuran / 1 h / -15 - 0 °C 4.1: trifluoroacetic acid; 1,1,3,3-tetramethyldisiloxane / 1,2-dichloro-ethane / 0.25 h / -20 - -10 °C 5.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 5.2: 1 h / 15 - 20 °C / pH 2 6.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 °C / Inert atmosphere 7.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 10 - 20 °C 8.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 8.2: -10 - 12 °C View Scheme

1.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1 h / -10 - 5 °C 2.1: tetrahydrofuran / 1 h / -15 - 0 °C 3.1: trifluoroacetic acid; 1,1,3,3-tetramethyldisiloxane / 1,2-dichloro-ethane / 0.25 h / -20 - -10 °C 4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 4.2: 1 h / 15 - 20 °C / pH 2 5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 °C / Inert atmosphere 6.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 10 - 20 °C 7.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 7.2: -10 - 12 °C View Scheme

1.1: tetrahydrofuran / 1 h / -15 - 0 °C 2.1: trifluoroacetic acid; 1,1,3,3-tetramethyldisiloxane / 1,2-dichloro-ethane / 0.25 h / -20 - -10 °C 3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 3.2: 1 h / 15 - 20 °C / pH 2 4.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 °C / Inert atmosphere 5.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 10 - 20 °C 6.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 6.2: -10 - 12 °C View Scheme