1: 5-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine With tetrabutylammomium bromide; sodium hydroxide in dichloromethane T=0°C; 0.0833333 h; 2: benzenesulfonyl chloride in dichloromethane T=0 - 25°C; 12.25 h;

hydrogenchloride in methanol 0.133333 h;

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C 2: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux View Scheme

1: 5-Bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride in DMF (N,N-dimethyl-formamide) T=0°C; 0.166667 h; 2: tert-butyldimethylsilyl chloride in DMF (N,N-dimethyl-formamide)

1.1: triethylamine; formic acid / palladium 10 on activated carbon / 120 h / 0 - 80 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 3 h / 0 °C 3.1: bromine; pyridine / dichloromethane / 2 h / 0 °C 4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 3 h / 0 °C 2.1: bromine; pyridine / dichloromethane / 2 h / 0 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h View Scheme

1: in tetrahydrofuran T=-78°C; 0.166667 h; 2: With sulfur in tetrahydrofuran T=-78°C; 2 h; 3: With iodine in tetrahydrofuran T=-78 - 20°C; 2.5 h;

sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; lithium chloride in ethanol; water; toluene T=20 - 105°C; Suzuki Coupling; 1 h;

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C 2.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 3.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C 3.2: 12.25 h / 0 - 25 °C View Scheme