potassium carbonate in N,N-dimethyl-formamide T=120°C; 12 h;

potassium carbonate in N,N-dimethyl-formamide T=20°C; 12 h; Inert atmosphere;

potassium carbonate in N,N-dimethyl-formamide T=120°C; 24 h; Inert atmosphere;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Hagihara-Sonogashira coupling; 3 h;

1.1: PPh3 / PdCl2; CuI / diethylamine / 50 - 55 °C 1.2: diethylamine / 12 h / 50 - 55 °C 2.1: KOH / methanol; tetrahydrofuran / 12 h / 20 °C 3.1: PPh3 / PdCl2; CuI / diethylamine / 50 - 55 °C 3.2: 61 percent / diethylamine / 12 h / 50 - 55 °C View Scheme

1: triphenylphosphine; triethylamine / bis(triphenylphosphine) palladium dichloride; copper(I) iodide / tetrahydrofuran / 2 h / Heating 2: KOH / toluene / Heating View Scheme