N-bromosuccinmide; sodium acetate in acetone T=20°C; 0.5 h; Title compound not separated from byproducts;

1: 65 percent / 1) s-butyllithium, tetramethylethylenediamine / 1) -70 deg C, THF-cyclohexane, 2) -40 deg C 2: 1 percent / acid View Scheme

1: 1) t-BuOK / 1) CH2Cl2, -15 deg C, 10 min, 2) CH2Cl2, 0 deg C, 1 h 2: 98 percent / i-Pr2NH, POCl3 / tetrahydrofuran / 1 h / -30 °C 3: 93 percent / NaBH4 / tetrahydrofuran; ethanol / 3 h / 20 °C 4: 1) t-BuOK / 1) THF, -40 deg C, 10 min, 2a) -40 deg C, 15 min, 2b) to 0 deg C 5: 5 percent aq. HClO4 / dioxane / Heating View Scheme

1: 1) t-BuOK / 1) CH2Cl2, -15 deg C, 10 min, 2) CH2Cl2, 0 deg C, 1 h 2: 98 percent / i-Pr2NH, POCl3 / tetrahydrofuran / 1 h / -30 °C 3: 1) t-BuOK / 1) THF, -40 deg C, 10 min, 2a) -40 deg C, 15 min, 2b) to 0 deg C 4: 86 percent / 5 percent aq. HClO4 / dioxane / 12 h / Heating View Scheme

1: 47 percent / NH4OAc, NaBH3CN / tetrahydrofuran; methanol / 96 h / Ambient temperature 2: 23 percent / 1 N HCl / methanol / 0.5 h / Heating View Scheme

(tBuO)2CrO2 in tetrachloromethane

1: NH2NH2•xH2O; triethylamine / ethanol / 2 h / |Reflux 2: triethylamine; iodine / 1,4-dioxane / 0.5 h 3: hydrogenchloride / ethanol; water / 2.5 h / |Reflux 4: potassium carbonate; indole; copper(l) iodide; N-methyl-2-(methylamino)ethylamine / dimethyl sulfoxide / 24 h / 100 °C / |Inert atmosphere View Scheme

1: NH2NH2•xH2O; triethylamine / ethanol / 2 h / |Reflux 2: triethylamine; iodine / 1,4-dioxane / 0.5 h 3: hydrogenchloride / ethanol; water / 2.5 h / |Reflux 4: potassium carbonate; 2,2,6,6-tetramethylheptane-3,5-dione; copper(l) iodide / dimethyl sulfoxide / 24 h / 100 °C / |Inert atmosphere View Scheme

1: (i) COCl2, ClCH2CH2Cl, (ii) /BRN= 2149816/, Py, (iii) aq. NaOAc 2: H2, NaOAc / Pt-C / methanol 3: aq. AcOH View Scheme