hydrogen; palladium on activated charcoal in ethanol T=20°C;

1: With bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran 24 h; Heating / reflux; 2: With hydrogenchloride in tetrahydrofuran; water T=80°C; 10 h;

1: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine in N,N-dimethyl-formamide T=20°C; Sonogashira coupling; Inert atmosphere; 2: With sodium hydroxide in N,N-dimethyl-formamide T=140°C; 3: With palladium 10 on activated carbon in N,N-dimethyl-formamide T=140°C;

1: 85 percent / tBuOK / 1-methyl-pyrrolidin-2-one / 7 h / 60 - 70 °C 2: 85 percent / H2 / Pd/C / ethanol / 20 °C View Scheme

sulfuric acid

hydrogenchloride

2: concentrated H2SO4 View Scheme

1: pyridine / dichloromethane 2: tetrabutyl ammonium fluoride / tetrahydrofuran 3: methanol View Scheme