copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; Sonogashira coupling;

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 4 h, 2.) THF, hexane, -78 deg C, 30 min; r.t., 2 h 2: 57 percent / Et3N / Pd(PPh3)2Cl2, CuI / dimethylformamide / 1.5 h / Ambient temperature View Scheme

ammonia in ethanol T=80°C; 2 h;