sodium amide; sodium t-butanolate in tetrahydrofuran T=55 - 60°C; Fischer Indole Synthesis; 48 h; Inert atmosphere;

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 4 h;

sulfuric acid in 1,4-dioxane T=60°C; Fischer indole synthesis; 2 h;

sodium tetrahydroborate in methanol; water T=20 - 100°C; Inert atmosphere;

sulfuric acid in 1,4-dioxane T=80°C; 3 h;

1: ruthenium(III) chloride polyhydrate / isopropanol acetate / 15 h / 80 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol; water / 20 - 100 °C / Inert atmosphere View Scheme

1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere 3.1: ruthenium(III) chloride polyhydrate / isopropanol acetate / 15 h / 80 °C / Inert atmosphere 4.1: sodium tetrahydroborate / methanol; water / 20 - 100 °C / Inert atmosphere View Scheme

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: dichloromethane / 20 °C / Inert atmosphere 4.1: ruthenium(III) chloride polyhydrate / isopropanol acetate / 15 h / 80 °C / Inert atmosphere 5.1: sodium tetrahydroborate / methanol; water / 20 - 100 °C / Inert atmosphere View Scheme

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: dichloromethane / 20 °C / Inert atmosphere 4.1: ruthenium(III) chloride polyhydrate / isopropanol acetate / 15 h / 80 °C / Inert atmosphere 5.1: sodium tetrahydroborate / methanol; water / 20 - 100 °C / Inert atmosphere View Scheme

1.1: trifluoroacetic acid / dichloromethane / 0 °C / |Inert atmosphere 1.2: 5 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C View Scheme