sodium azide in N,N-dimethyl-formamide T=65°C; 6 h;

1: 81 percent / NaI / dimethylformamide / 3 h / 100 °C 2: 98 percent / H2, quinoline / Pd/BaSO4 / ethyl acetate 3: 11.9 g / KOH / ethanol; H2O / 12 h / 90 °C 4: 87 percent / BF3*Et2O / 5 h / 60 °C 5: 14.2 g / NEt3 / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h 6: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C View Scheme

1: 98 percent / H2, quinoline / Pd/BaSO4 / ethyl acetate 2: 11.9 g / KOH / ethanol; H2O / 12 h / 90 °C 3: 87 percent / BF3*Et2O / 5 h / 60 °C 4: 14.2 g / NEt3 / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h 5: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C View Scheme

1: 11.9 g / KOH / ethanol; H2O / 12 h / 90 °C 2: 87 percent / BF3*Et2O / 5 h / 60 °C 3: 14.2 g / NEt3 / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h 4: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C View Scheme

1: 87 percent / BF3*Et2O / 5 h / 60 °C 2: 14.2 g / NEt3 / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h 3: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C View Scheme

1: 14.2 g / NEt3 / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h 2: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C View Scheme