dipotassium hydrogenphosphate; 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride in ethanol; water; N,N-dimethyl-formamide T=20°C; Suzuki-Miyaura coupling; 25 h; Inert atmosphere;

1: potassium hydroxide / tetrahydrofuran; methanol; water / 46 h / 20 °C / Cooling 2: S-(-)-N-methyl-alpha-methylbenzylamine / isopropanol acetate / 20 - 23 °C / Resolution of racemate View Scheme

1: N-ethyl-N,N-diisopropylamine; magnesium chloride / dichloromethane / 24 h / 22 °C 2: DBDMH; trifluoroacetic acid / acetonitrile / 17 h / 60 °C 3: potassium hydroxide / tetrahydrofuran; methanol; water / 46 h / 20 °C / Cooling 4: S-(-)-N-methyl-alpha-methylbenzylamine / isopropanol acetate / 20 - 23 °C / Resolution of racemate View Scheme

1: bromine / chloroform 2: thionyl chloride 3: AlCl3, aluminium chloride 4: sodium hydroxide 5: S-(-)-N-methyl-alpha-methylbenzylamine / isopropanol acetate / 20 - 23 °C / Resolution of racemate View Scheme

1: N-ethyl-N,N-diisopropylamine; magnesium chloride / dichloromethane / 24 h / 22 °C 2: DBDMH; trifluoroacetic acid / acetonitrile / 17 h / 60 °C 3: potassium hydroxide / tetrahydrofuran; methanol; water / 46 h / 20 °C / Cooling 4: S-(-)-N-methyl-alpha-methylbenzylamine / isopropanol acetate / 20 - 23 °C / Resolution of racemate View Scheme

1: With sodium hydrogencarbonate in DMF (N,N-dimethyl-formamide) T=20°C; 2: With hydrogenchloride in DMF (N,N-dimethyl-formamide); water T=15°C; pH=< 7; 1 h;

1: sodium hydrogencarbonate / N,N-dimethyl-formamide 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / ethanol; water; N,N-dimethyl-formamide; toluene 3: iron; ammonium chloride View Scheme