PPA T=140°C;

1: 5-chloro-1H-indole With sodium hydride in N,N-dimethyl-formamide T=1 - 20°C; 1 h; Inert atmosphere; 2: benzyl bromide in N,N-dimethyl-formamide T=20°C; 12 h; Inert atmosphere;

tris(p-fluoro phenyl)phosphine; [RhCl(η2:η2-cycloocta-1,5-diene)]2 in N,N-dimethyl-formamide T=85°C; 2 h;

propylsulfonic acid-functionalized silica in toluene Reflux;

1: 5-chloro-1H-indole With potassium hydroxide in ethanol T=20°C; 0.0833333 h; 2: 5-Bromo-1H-indole in acetone T=20°C; 0.0833333 h;

1: benzyltrimethylammonium iodine dichloride; CaCO3 / CH2Cl2; methanol / 25 °C 2: CuI; diethylamine / PdCl2(PPh3)2 / 25 °C 3: potassium carbonate / methanol / 25 °C 4: 88 percent / tris(4-fluorophenyl)phosphine / [Rh(COD)Cl]2 / dimethylformamide / 2 h / 85 °C View Scheme

1: 5-chloro-1H-indole With potassium hydroxide in N,N-dimethyl-formamide T=20°C; 0.5 h; Inert atmosphere; 2: benzylhalide in N,N-dimethyl-formamide Inert atmosphere;

1: potassium carbonate / N,N-dimethyl-formamide / 20 - 80 °C / |Inert atmosphere 2: propylsulfonic acid-functionalized silica / toluene / |Reflux View Scheme