copper(l) iodide; potassium iodide; N-methyl-2-(methylamino)ethylamine in toluene T=110°C; Rosenmund-von Braun reaction; 24 h;

1: 1H-indole-5-carbonitrile With sodium hydride in tetrahydrofuran; mineral oil T=0 - 23°C; Inert atmosphere; 2: p-toluenesulfonyl chloride in tetrahydrofuran; mineral oil T=0 - 23°C; Inert atmosphere;

1: 99 percent / tetrabutylammonium hydrogen sulfate; KOH / toluene; H2O / 20 °C 2: 90 percent / CuI; KI; 1,2-di(N-methylamino)ethane / toluene / 24 h / 110 °C View Scheme

1: 99 percent / tetrabutylammonium hydrogen sulfate; KOH / toluene; H2O / 20 °C 2: 90 percent / CuI; KI; 1,2-di(N-methylamino)ethane / toluene / 24 h / 110 °C View Scheme

in tetrahydrofuran; NaH; hexane; water; mineral oil

1.1: AlCl3, aluminium chloride / dichloromethane / 8 h / 20 °C / |Large scale 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 6 h / 15 - 20 °C / |Large scale 3.1: triethylamine; potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C / |Large scale 4.1: sodium hydroxide / methanol / 4 h / |Reflux; |Large scale 5.1: 1,1'-carbonyldiimidazole / methanol / 1 h / 20 °C / |Reflux; |Large scale 5.2: 0.5 h / |Large scale View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 2 h / 20 °C 2: potassium tert-butylate / tetrahydrofuran / Inert atmosphere; Reflux View Scheme