pyridine in dichloromethane T=0 - 20°C; 3 h;

1: sodium hydrogencarbonate / ethanol / Reflux 2: 1,10-phenanthroline; caesium carbonate; copper(I) bromide / 24 h / 110 °C 3: copper / toluene / 1 h / Reflux 4: sodium tetrahydroborate / tetrahydrofuran; ethanol / Reflux 5: tetrachloromethane; sodium azide; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 90 °C 6: palladium 10 on activated carbon; hydrogen / methanol / 20 °C 7: pyridine / dichloromethane / 3 h / 0 - 20 °C View Scheme

1: sodium tetrahydroborate / tetrahydrofuran; ethanol / Reflux 2: tetrachloromethane; sodium azide; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 90 °C 3: palladium 10 on activated carbon; hydrogen / methanol / 20 °C 4: pyridine / dichloromethane / 3 h / 0 - 20 °C View Scheme

1: tetrachloromethane; sodium azide; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 90 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 20 °C 3: pyridine / dichloromethane / 3 h / 0 - 20 °C View Scheme

1: copper / toluene / 1 h / Reflux 2: sodium tetrahydroborate / tetrahydrofuran; ethanol / Reflux 3: tetrachloromethane; sodium azide; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 90 °C 4: palladium 10 on activated carbon; hydrogen / methanol / 20 °C 5: pyridine / dichloromethane / 3 h / 0 - 20 °C View Scheme

1: 1,10-phenanthroline; caesium carbonate; copper(I) bromide / 24 h / 110 °C 2: copper / toluene / 1 h / Reflux 3: sodium tetrahydroborate / tetrahydrofuran; ethanol / Reflux 4: tetrachloromethane; sodium azide; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 90 °C 5: palladium 10 on activated carbon; hydrogen / methanol / 20 °C 6: pyridine / dichloromethane / 3 h / 0 - 20 °C View Scheme