triethylamine; palladium diacetate; triphenylphosphine in N,N-dimethyl-formamide T=100°C; 3 h;

potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct in tetrahydrofuran; N,N-dimethyl-formamide T=70°C; Suzuki-Miyaura cross-coupling; 6 h;

1: SOCl2 / neat (no solvent) / 24 h / Heating 2: bromine / 1 h / 150 °C 3: CH2Cl2 / 1. ice bath 2. 30 min reflux 4: 98 percent / NEt3 / Pd(OAc)2, PPh3 / dimethylformamide / 3 h / 100 °C View Scheme

1: bromine / 1 h / 150 °C 2: CH2Cl2 / 1. ice bath 2. 30 min reflux 3: 98 percent / NEt3 / Pd(OAc)2, PPh3 / dimethylformamide / 3 h / 100 °C View Scheme

1: CH2Cl2 / 1. ice bath 2. 30 min reflux 2: 98 percent / NEt3 / Pd(OAc)2, PPh3 / dimethylformamide / 3 h / 100 °C View Scheme

1: methyl 5-amino-3-pyridinecarboxylate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane With tert.-butylnitrite in acetonitrile T=80°C; 2 h; 2: iodobenzene With tetrakis(triphenylphosphine) palladium(0); potassium carbonate in N,N-dimethyl-formamide T=100°C; Suzuki-Miyaura Coupling; 12 h; Inert atmosphere;

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran T=50°C; 3 h;

sodium hydroxide; LiAlH4 in tetrahydrofuran

1: platinum(IV) oxide; sulfuric acid; hydrogen / ethanol / 24 h / 20 °C / 2585.81 Torr 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 18 h / 20 °C 3: sodium hydroxide / methanol / 18 h / Reflux View Scheme