1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 2: (N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)CuOtBu; 1,1,3,3-tetramethyldisiloxane; cesium fluoride / 1,4-dioxane / 4 h / 25 °C / |Glovebox; |Inert atmosphere View Scheme

sodium azide in acetone Heating;

1: 76 percent / K2CO3 / dimethylformamide / 5 h / 60 - 70 °C 2: 80 percent / NEt3 / CH2Cl2 / 6 h / 20 °C 3: 94 percent / K2CO3 / dimethylformamide / 9 h / 60 - 70 °C 4: 0.9 g / H2NNH2*H2O / ethanol / 18 h / Heating View Scheme

potassium carbonate in N,N-dimethyl-formamide T=60 - 70°C; 5 h;