1: With potassium tert-butylate in tetrahydrofuran T=5 - 20°C; 2: With ammonium chloride in tetrahydrofuran; water; ethyl acetate 0.166667 h;

1.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 18 h / 0 - 20 °C 2.1: hydrogen; zinc dibromide / palladium 10 on activated carbon / ethyl acetate / 48 h / 20 °C 3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 5 - 20 °C 3.2: 0.17 h View Scheme

1.1: hydrogen; zinc dibromide / palladium 10 on activated carbon / ethyl acetate / 48 h / 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 5 - 20 °C 2.2: 0.17 h View Scheme

1.1: thionyl chloride; triethylamine / dichloromethane / 3.5 h / 32 °C 2.1: triethylamine / 8 h / Reflux 3.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 18 h / 0 - 20 °C 4.1: hydrogen; zinc dibromide / palladium 10 on activated carbon / ethyl acetate / 48 h / 20 °C 5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 5 - 20 °C 5.2: 0.17 h View Scheme

1.1: triethylamine / 8 h / Reflux 2.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 18 h / 0 - 20 °C 3.1: hydrogen; zinc dibromide / palladium 10 on activated carbon / ethyl acetate / 48 h / 20 °C 4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 5 - 20 °C 4.2: 0.17 h View Scheme