1: mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / |Inert atmosphere 2: potassium hydroxide / toluene; methanol / 2 h / |Inert atmosphere; |Reflux 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / |Inert atmosphere 4: triethylamine / dichloromethane / 14 h / |Inert atmosphere View Scheme

1: N-pentylindole With dimethylaluminum chloride in hexane; dichloromethane T=0°C; Friedel-Crafts reaction; 0.5 h; Inert atmosphere; 2: 8-bromo-1-naphthoyl chloride in hexane; dichloromethane T=0 - 20°C; Friedel-Crafts reaction; Inert atmosphere;

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: N-pentylindole With dimethylaluminum chloride in hexane; dichloromethane T=0°C; Friedel-Crafts reaction; 1 h; Inert atmosphere; 2: C11H6Cl2O in hexane; dichloromethane T=0 - 20°C; Friedel-Crafts reaction; 6 h; Inert atmosphere;

1: indole With sodium hydride in N,N-dimethyl-formamide; mineral oil T=5 - 20°C; Inert atmosphere; 2: n-bromopentane in N,N-dimethyl-formamide; mineral oil T=5 - 20°C; 16 h; Inert atmosphere;

in benzene 25 h; Heating;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene 4 h; Yield given. Yields of byproduct given;

1: mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / |Inert atmosphere 2: potassium hydroxide / toluene; methanol / 2 h / |Inert atmosphere; |Reflux 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / |Inert atmosphere 4: triethylamine / dichloromethane / 14 h / |Inert atmosphere View Scheme

1: mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / |Inert atmosphere 2: potassium hydroxide / toluene; methanol / 2 h / |Inert atmosphere; |Reflux View Scheme