1: 2-(pent-4-en-1-yl)-1H-indole With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.166667 h; 2: benzyl chloride in N,N-dimethyl-formamide T=20°C; 4 h;

1.1: n-BuLi / tetrahydrofuran; hexane / 6 h / Heating 1.2: 62 percent / hexane; tetrahydrofuran / 1 h / 20 °C 2.1: NaH / dimethylformamide / 0.17 h / 0 °C 2.2: 73 percent / dimethylformamide / 4 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 6 h / Heating 1.2: 62 percent / hexane; tetrahydrofuran / 1 h / 20 °C 2.1: NaH / dimethylformamide / 0.17 h / 0 °C 2.2: 73 percent / dimethylformamide / 4 h / 20 °C View Scheme