1: 5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.333333 h; 2: ethyl [p-(chloromethyl)phenoxy]acetate in N,N-dimethyl-formamide T=20°C; 18 h; Further stages.;

1.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C 1.2: 59 percent / dimethylformamide / 18 h / 20 °C 2.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 3.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C 4.1: tetrahydrofuran 5.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C View Scheme

thionyl chloride in dichloromethane; N,N-dimethyl-formamide T=0°C; 0.75 h; Inert atmosphere;

1: K2CO3 2: SOCl2 / tetrahydrofuran View Scheme

1.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C 1.2: 59 percent / dimethylformamide / 18 h / 20 °C 2.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 3.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C 4.1: tetrahydrofuran View Scheme