1: 2-bromo-pyridine With tert.-butyl lithium in tetrahydrofuran; pentane T=-78°C; 0.416667 h; 2: With zinc(II) chloride in tetrahydrofuran; diethyl ether; pentane T=-78 - 20°C; 2 h; 3: 3-bromo-1-iodobenzene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; diethyl ether; pentane T=20°C; 92 h;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethylene glycol dimethyl ether; ethanol; water Suzuki coupling; 18 h; Reflux;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in tetrahydrofuran T=80°C; Suzuki-Miyaura reaction; 24 h;

tetrakis(triphenylphosphine) palladium(0) in toluene 24 h; Inert atmosphereReflux;

sodium carbonate

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane T=20°C; 51 h;

1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -86 °C 1.2: 2 h / -86 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / 51 h / 20 °C View Scheme

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2: With boric acid trimethyl ester in tetrahydrofuran; hexane T=-60 - 20°C; 3: With hydrogenchloride in tetrahydrofuran; hexane; water 0.5 h;