sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane; water Suzuki cross-coupling; 18 h; Heating;

1.1: 95 percent / LDA 2.1: trimethyltin chloride; n-BuLi 2.2: 53 percent / Pd(PPh3)4 View Scheme

1: 3-iodo-2-chloropyridine With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 2: carbon dioxide in tetrahydrofuran

1.1: 79 percent / butyllithium; diisopropylamine / tetrahydrofuran; hexane / 4 h / -75 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / 0 °C 2.2: 67 percent / N-chlorosuccinimide / tetrahydrofuran / 1 h / 25 °C 3.1: diisopropylamine; butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C 3.2: 81 percent / iodine / tetrahydrofuran 4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -75 °C 4.2: 26 percent / silica gel; H2O / CH2Cl2; hexane 5.1: tert-butyllithium / pentane; diethyl ether / 0.25 h / -75 °C 5.2: 79 percent / -78 °C View Scheme

iso-propylmagnesium bromide 1.) THF, -40 deg C, 0.5 h, 2.) THF, -40 to 0 deg C; Yield given. Multistep reaction;

ammonia in ethanol T=180°C; 48 h;

triethylamine; palladium diacetate T=120°C; 24 h;

1: 67 percent / NH3 / ethanol / 48 h / 180 °C 2: 78 percent / Et3N / Pd(OAc)2 / acetonitrile / 24 h / 120 °C 3: 83 percent / NaOEt / ethanol / 3 h / Heating View Scheme

lithium diisopropyl amide in tetrahydrofuran 1.) -75 deg C, 3 h, 2.) -75 deg C, 2 h;

lithium diisopropyl amide