1: c-octyl-Br With chloro-trimethyl-silane; magnesium; ethylene dibromide; lithium chloride; zinc dibromide in tetrahydrofuran T=25°C; 2 h; Inert atmosphere; 2: benzenediazonium tetrafluoroborate in tetrahydrofuran T=-60 - 25°C; Inert atmosphere; 3: 1-dimethylamino-3-chloropropane Further stages;

1: 2,3,4,5,6,7-Hexahydro-1H-cyclooctlt;bgt;indol With potassium tert-butylate; tetra-(n-butyl)ammonium iodide in N,N-dimethyl-formamide T=20°C; 2 h; Inert atmosphere; 2: 1-dimethylamino-3-chloropropane in N,N-dimethyl-formamide T=60 - 120°C; 5.5 h; Inert atmosphere;

1.1: ethanol; potassium hydroxide / 14 h / 80 °C / Inert atmosphere 2.1: potassium tert-butylate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 2.2: 5.5 h / 60 - 120 °C / Inert atmosphere View Scheme

1.1: N,N-dimethyl-formamide / 5 h / 100 °C / Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 66 h / 20 °C / 7600.51 Torr / Autoclave 3.1: ethanol; potassium hydroxide / 14 h / 80 °C / Inert atmosphere 4.1: potassium tert-butylate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 4.2: 5.5 h / 60 - 120 °C / Inert atmosphere View Scheme