1: With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine in toluene T=110°C; Fischer Indole Synthesis; 40 h; Schlenk techniqueInert atmosphere; 2: With zinc(II) chloride in toluene T=90°C; Fischer Indole Synthesis; 1 h;

1.1: 1.5 h / 20 - 80 °C / |Inert atmosphere 2.1: sodium / ethanol / 20 h / 100 °C / |Sealed tube; |Darkness 3.1: copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine / toluene / 40 h / 110 °C / |Schlenk technique; |Inert atmosphere 3.2: 1 h / 90 °C View Scheme

1.1: triphenyl phosphite; bromine; triethylamine / dichloromethane / 20 h / -60 - 20 °C / |Inert atmosphere; |Reflux 2.1: copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine / toluene / 40 h / 110 °C / |Schlenk technique; |Inert atmosphere 2.2: 1 h / 90 °C View Scheme

1.1: sodium / ethanol / 20 h / 100 °C / |Sealed tube; |Darkness 2.1: copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine / toluene / 40 h / 110 °C / |Schlenk technique; |Inert atmosphere 2.2: 1 h / 90 °C View Scheme

potassium hydroxide 1.) acetone, 2.) room temp., 8 min; Yield given. Multistep reaction;