1: N-pentylindole With dimethylaluminum chloride in hexane; dichloromethane T=0°C; Friedel-Crafts reaction; 0.5 h; Inert atmosphere; 2: 4-bromo-1-naphthoic acid chloride in hexane; dichloromethane T=0 - 20°C; Friedel-Crafts reaction; Inert atmosphere;

1: 3-(4-bromo-1-naphthoyl)indole With potassium hydroxide in dimethyl sulfoxide T=20°C; 1 h; 2: n-bromopentane in dimethyl sulfoxide T=20°C; 6 h;

1.1: AlCl3, aluminium chloride / carbon disulfide / 120 h / 0 - 20 °C / Inert atmosphere 2.1: iodine / 0.67 h / Inert atmosphere; Reflux 3.1: water; sodium hydroxide / 2 h / Reflux 4.1: thionyl chloride / 2 h / Inert atmosphere; Reflux 5.1: dimethylaluminum chloride / hexane; dichloromethane / 0.5 h / 0 °C / Inert atmosphere 5.2: 0 - 20 °C / Inert atmosphere View Scheme

1.1: thionyl chloride / 2 h / Inert atmosphere; Reflux 2.1: dimethylaluminum chloride / hexane; dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere View Scheme

1.1: iodine / 0.67 h / Inert atmosphere; Reflux 2.1: water; sodium hydroxide / 2 h / Reflux 3.1: thionyl chloride / 2 h / Inert atmosphere; Reflux 4.1: dimethylaluminum chloride / hexane; dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4.2: 0 - 20 °C / Inert atmosphere View Scheme