triethylamine; palladium diacetate in acetonitrile T=120°C; 24 h;

1: 1.) sodium nitrite, HCl; 2.) KI / 1.) 0 deg C, H2O; 2.) H2O, 30 min at RT then 30 min at 60 deg C 2: 67 percent / NH3 / ethanol / 48 h / 180 °C 3: 78 percent / Et3N / Pd(OAc)2 / acetonitrile / 24 h / 120 °C View Scheme

1: 67 percent / NH3 / ethanol / 48 h / 180 °C 2: 78 percent / Et3N / Pd(OAc)2 / acetonitrile / 24 h / 120 °C View Scheme

sodium ethanolate in ethanol 3 h; Heating;