1: 5-Bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.5 h; 2: methyl iodide in N,N-dimethyl-formamide T=0 - 20°C; 12 h;

1.1: 85 percent / bromine / 2-methyl-propan-2-ol; H2O / 20 °C 2.1: 94 percent / zinc; acetic acid / 20 °C 3.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 3.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C 4.1: sodium hydride in oil / dimethylformamide / 0.5 h / 0 °C 4.2: 63 percent / dimethylformamide / 12 h / 0 - 20 °C View Scheme

1.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 1.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C 2.1: sodium hydride in oil / dimethylformamide / 0.5 h / 0 °C 2.2: 63 percent / dimethylformamide / 12 h / 0 - 20 °C View Scheme

1.1: 94 percent / zinc; acetic acid / 20 °C 2.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 2.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C 3.1: sodium hydride in oil / dimethylformamide / 0.5 h / 0 °C 3.2: 63 percent / dimethylformamide / 12 h / 0 - 20 °C View Scheme