2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in tetrahydrofuran Dehalogenation; 18 h; Heating;

1: With ammonia in methanol T=20°C; Deacetylation; 2: With sodium acetate in N,N-dimethyl-formamide T=130°C; Elimination; 1.5 h; Further stages.;

1.1: (NH4)2SO4; HMDS / m-xylene / Heating 1.2: 51 percent / TMSOTf / 1,2-dichloro-ethane / 18 h / Heating 2.1: H2; Et3N / 10percent Pd/C / dioxane / 4 h / 20 °C / 1292.9 Torr 3.1: NH3 / methanol / 20 °C 3.2: NaOAc / dimethylformamide / 1.5 h / 130 °C View Scheme

1.1: (NH4)2SO4; HMDS / m-xylene / Heating 1.2: 51 percent / TMSOTf / 1,2-dichloro-ethane / 18 h / Heating 2.1: H2; Et3N / 10percent Pd/C / dioxane / 4 h / 20 °C / 1292.9 Torr 3.1: NH3 / methanol / 20 °C 3.2: NaOAc / dimethylformamide / 1.5 h / 130 °C View Scheme

1.1: H2; Et3N / 10percent Pd/C / dioxane / 4 h / 20 °C / 1292.9 Torr 2.1: NH3 / methanol / 20 °C 2.2: NaOAc / dimethylformamide / 1.5 h / 130 °C View Scheme