hydrogenchloride; water in 1,4-dioxane T=60°C; 16 h; Inert atmosphere;

methanol; sodium hydroxide T=70°C; 1.5 h;

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1.5 h / 0 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -35 °C 2.2: 2 h / -35 - 20 °C 3.1: sodium hydroxide; water / 1,4-dioxane / 17 h / 60 - 80 °C View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 1.2: 0.5 h / -78 °C 2.1: sodium hydroxide; methanol / 1.5 h / 70 °C View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -35 °C 1.2: 2 h / -35 - 20 °C 2.1: sodium hydroxide; water / 1,4-dioxane / 17 h / 60 - 80 °C View Scheme

1: 4-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine With sodium hydride in tetrahydrofuran; mineral oil T=0°C; Inert atmosphere; 2: With n-butyllithium in tetrahydrofuran; hexanes; mineral oil T=-78°C; Inert atmosphere; 3: tri-isopropoxy-borane