1.1: t-BuLi / pentane; tetrahydrofuran / 0.17 h / -78 °C 1.2: pentane; tetrahydrofuran / 0.25 h / -78 °C 2.1: 190 mg / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C View Scheme

1: 79 percent / t-BuLi / tetrahydrofuran; pentane / 2 h / -78 °C 2: 97 percent / Me2NH / tetrahydrofuran / 3 h / 20 °C View Scheme

1: 3-Bromo-1-(tert-butyldimethylsilyl)-6-methoxyindole With tert.-butyl lithium in tetrahydrofuran; pentane T=-78°C; 0.166667 h; 2: methyl iodide in tetrahydrofuran; pentane T=-78°C; 0.25 h; 3: With tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 0.166667 h;