pyridine in dichloromethane T=20°C; 24 h;

triphenylphosphine; lithium chloride; palladium diacetate in N,N-dimethyl acetamide T=100°C; Stille coupling; 21 h;

1: 66 percent / BF3*Et2O / xylene / 2 h / 180 °C 2: 98 percent / pyridine / CH2Cl2 / 0 - 20 °C View Scheme

1: 89 percent / NaH / various solvent(s); tetrahydrofuran / 21 h / Heating 2: 86 percent / (Cy3P)2Ru(=CHPh)Cl2 / toluene / 24 h / 60 °C 3: 90 percent / H2 / Pd/C / methanol / 48 h / 20 °C 4: BH3*SMe2 / tetrahydrofuran / Heating View Scheme