1: N-iodo-succinimide / N,N-dimethyl-formamide / 20 - 55 °C 2: tetrahydrofuran / 1 h / Cooling with ice 3: triethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 5 h / 50 °C / Inert atmosphere; Cooling with acetone-dry ice 4: copper(l) iodide / N,N-dimethyl-formamide / 110 °C / Inert atmosphere View Scheme

TEA in benzene 5 h; Heating;

1.1: hydrobromic acid; sodium nitrite / H2O 1.2: 97 percent / potassium bromide / H2O 2.1: lithium diisopropylamide / tetrahydrofuran / -70 °C 2.2: 82 percent / iodine / tetrahydrofuran / -70 °C 3.1: 80 percent / sodium acetate; potassium bromide / palladium(II) acetate / various solvent(s) / 90 - 100 °C 4.1: 91 percent / tetrabutylammonium bromide; triphenylphosphine; sodium carbonate / palladium(II) acetate; potassium chloride / toluene; H2O / Heating 5.1: 88 percent / 3-chloroperoxybenzoic acid / toluene / 24 h / 20 °C 6.1: 85 percent / phosphorus oxychloride View Scheme

T=135°C; 16 h;

1: 2-(dimethylamino)-ethanol With sodium hydride in toluene T=20°C; 0.666667 h; 2: 4-Amino-2-chloropyridine in toluene 16 h; Heating / reflux;

1.1: hydrobromic acid; sodium nitrite / H2O 1.2: 97 percent / potassium bromide / H2O 2.1: lithium diisopropylamide / tetrahydrofuran / -70 °C 2.2: 82 percent / iodine / tetrahydrofuran / -70 °C 3.1: 80 percent / sodium acetate; potassium bromide / palladium(II) acetate / various solvent(s) / 90 - 100 °C View Scheme

N-ethyl-N,N-diisopropylamine; sodium iodide in butan-1-ol T=120°C; 24 h;

pyridine in dichloromethane T=0°C; 3 h;

1.1: toluene-4-sulfonic acid / toluene / |Heating 2.1: tert.-butyl lithium / tetrahydrofuran / -78 °C 2.2: 20 °C 3.1: hydroxylamine hydrochloride; triethylamine / ethanol; water / |Heating View Scheme

in 1-methyl-pyrrolidin-2-one T=200°C; 0.222222 h; Sealed vesselMicrowave irradiation;