ammonia in ethanol T=90°C; 24 h;

1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: sodium ethanolate / toluene / 4 h / 80 °C 3: acetonitrile; water / 3 h / Reflux View Scheme

1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2.1: sodium ethanolate / toluene / 4 h / 80 °C 3.1: acetonitrile; water / 3 h / Reflux 4.1: bromine / tetrahydrofuran / 0.17 h / 20 °C 4.2: 2 h / 80 °C 5.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 2 h / 20 °C 6.1: caesium carbonate / palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / acetonitrile / 16 h / 85 °C / Inert atmosphere View Scheme

triethylamine in dichloromethane T=0 - 20°C; 2 h; Inert atmosphere;