1: 4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine With sodium hydride in N,N-dimethyl-formamide Inert atmosphere; 2: tert-butyl methyl ether With iodine T=0 - 20°C;

1.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / acetonitrile / 0.5 h / 20 °C / Inert atmosphere 1.2: 30 - 40 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1.83 h / -78 °C / Inert atmosphere 2.2: 4 h / -78 °C 3.1: bromo-catecholborane / dichloromethane / 1.5 h 4.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere 4.2: 0 - 20 °C View Scheme

1.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1.83 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 °C 2.1: bromo-catecholborane / dichloromethane / 1.5 h 3.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere 3.2: 0 - 20 °C View Scheme

1.1: bromo-catecholborane / dichloromethane / 1.5 h 2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere 2.2: 0 - 20 °C View Scheme