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;

1: 5-Bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride in tetrahydrofuran T=0°C; 0.5 h; 2: benzenesulfonyl chloride in tetrahydrofuran T=5 - 20°C; Product distribution / selectivity;

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 5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C 5.2: 12.25 h / 0 - 25 °C 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 4.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C 4.2: 12.25 h / 0 - 25 °C View Scheme

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -35 °C 1.2: 2 h / -35 - 20 °C 2.1: sodium hydroxide / methanol / 2 h / Reflux View Scheme

1: 5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-35°C; 0.5 h; 2: methyl iodide in tetrahydrofuran; hexane T=-35 - 20°C; 2 h;