sulfur(IV) fluoride in hydrogen fluoride T=70°C; 20 h;

toluene-4-sulfonic acid T=64°C; 24 h;

methanol; thionyl chloride T=25°C; 4 h; Heating / reflux;

1: 3.82 g / HCl(g) / 5 h / Heating 2: pyridine / dimethylformamide / 6 h / 160 °C 3: aq. NaOH / methanol / 20 °C 4: 4.2 g / Et3N; phosphorazidic acid diphenyl ester / 72 h View Scheme

1.1: 3.82 g / HCl(g) / 5 h / Heating 2.1: pyridine / dimethylformamide / 6 h / 160 °C 3.1: aq. NaOH / methanol / 20 °C 4.1: 4.2 g / Et3N; phosphorazidic acid diphenyl ester / 72 h 5.1: pyridine / acetic acid / 0.5 h 5.2: 2.71 g / Raney Ni; pyridine / acetic acid / 1.5 h / 46 °C View Scheme

1.1: 3.82 g / HCl(g) / 5 h / Heating 2.1: pyridine / dimethylformamide / 6 h / 160 °C 3.1: aq. NaOH / methanol / 20 °C 4.1: 4.2 g / Et3N; phosphorazidic acid diphenyl ester / 72 h 5.1: pyridine / acetic acid / 0.5 h 5.2: 2.71 g / Raney Ni; pyridine / acetic acid / 1.5 h / 46 °C 6.1: NaBH4 / ethanol / 2 h / 20 °C View Scheme

sodium carbonate; bis-triphenylphosphine-palladium(II) chloride in water; acetonitrile Suzuki Coupling; 22 h; Heating / reflux;

1: 3.82 g / HCl(g) / 5 h / Heating 2: pyridine / dimethylformamide / 6 h / 160 °C View Scheme

ammonia in pyridine; hexane; chloroform

1.1: toluene-4-sulfonic acid / 24 h / 64 °C 2.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 72 h / Reflux 3.1: sodium hydroxide / methanol; water / 12 h / 20 °C 3.2: pH 2 4.1: ammonia; sodium / tetrahydrofuran / 2.5 h / -70 °C / Inert atmosphere 4.2: ice / pH 3 5.1: diphenyl phosphoryl azide; triethylamine / benzene / 6 h / 80 °C 5.2: 30 h / 80 °C 6.1: palladium on carbon; chloroform; hydrogen / methanol / 24 h / 20 °C View Scheme