copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=120°C; Reduction; 56 h;

1: 90 percent / acetonitrile / 3 h / Heating 2: 74.5 percent / NaH / acetonitrile 3: 76.5 percent / NH3 / methanol / 48 h / Ambient temperature 4: 97 percent / pyridine / 4 h / Ambient temperature 5: 56 percent / KF, N,O-bis(trimethylsilyl)acetamide / 18-crown-6 ether / acetonitrile / 12 h / Heating 6: 82 percent / NH3 / methanol / 12 h / Ambient temperature View Scheme

1: 74.5 percent / NaH / acetonitrile 2: 76.5 percent / NH3 / methanol / 48 h / Ambient temperature 3: 97 percent / pyridine / 4 h / Ambient temperature 4: 56 percent / KF, N,O-bis(trimethylsilyl)acetamide / 18-crown-6 ether / acetonitrile / 12 h / Heating 5: 82 percent / NH3 / methanol / 12 h / Ambient temperature View Scheme

in pyridine T=110°C; Substitution; 10 h;

water