1: With sodium hydroxide in ethanol T=20°C; 2 h; 2: With hydrogenchloride in water

1: 3-iodo-pyridine With indium; n-tetradec-1l-ene; lithium chloride in tetrahydrofuran T=50°C; 5 h; 2: 4-iodobenzoic acid ethyl ester With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran; 1-methyl-pyrrolidin-2-one 17 h; RefluxInert atmosphere;

1: 4-iodobenzoic acid ethyl ester With chloro-trimethyl-silane; ethylene dibromide; lithium chloride; zinc in tetrahydrofuran T=50°C; 10 h; Inert atmosphere; 2: 3-bromo-pyridine With PEPPSI-IPr catalyst in tetrahydrofuran T=50°C; Negishi cross-coupling; 3 h; Inert atmosphere;

potassium hydroxide; tetrabutylammomium bromide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran Substitution; 20 h; Heating;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether 15 h; Heating / reflux;

1,10-phenanthroline; palladium diacetate; caesium carbonate T=140°C; 48 h; Sealed tube;