1: 3-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine With sodium hydride in DMF (N,N-dimethyl-formamide) 0.5 h; 2: p-toluenesulfonyl chloride in DMF (N,N-dimethyl-formamide) T=20°C; 18 h;

1: 3-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine With sodium hydride in N,N-dimethyl-formamide; mineral oil T=0°C; 0.833333 h; Inert atmosphere; 2: p-toluenesulfonyl chloride in N,N-dimethyl-formamide; mineral oil T=0 - 25°C; 1.5 h;

1.1: iodine; sulfuric acid; periodic acid / ethanol; water / 15 h / 80 °C 1.2: pH 9 2.1: triethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1.67 h / 20 - 40 °C / Inert atmosphere 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 80 °C / Inert atmosphere 4.1: bromine; acetic acid / 3 h / 90 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere 5.2: 1.5 h / 0 - 25 °C View Scheme

1.1: triethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1.67 h / 20 - 40 °C / Inert atmosphere 2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 80 °C / Inert atmosphere 3.1: bromine; acetic acid / 3 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere 4.2: 1.5 h / 0 - 25 °C View Scheme

1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 80 °C / Inert atmosphere 2.1: bromine; acetic acid / 3 h / 90 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 - 25 °C View Scheme

1.1: bromine; acetic acid / 3 h / 90 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere 2.2: 1.5 h / 0 - 25 °C View Scheme

potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in ethylene glycol dimethyl ether T=90°C; 18 h;