sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate in dichloromethane T=20°C; 1 h;

1: 4-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.166667 h; 2: p-toluenesulfonyl chloride in N,N-dimethyl-formamide T=0 - 20°C;

1.1: [14C]-Tetramethylammonium bromide; trifluoromethanesulfonic anhydride / N,N-dimethyl-formamide / 24.5 h / 0 - 20 °C / Inert atmosphere 1.2: pH 7 2.1: sodium hydroxide / tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 1 h / 20 °C View Scheme

1.1: n-heptane; ethylene glycol dimethyl ether / 19 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / water / 2 h / 20 °C / pH 10 3.1: [14C]-Tetramethylammonium bromide; trifluoromethanesulfonic anhydride / N,N-dimethyl-formamide / 24.5 h / 0 - 20 °C / Inert atmosphere 3.2: pH 7 4.1: sodium hydroxide / tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 1 h / 20 °C View Scheme

potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in ethylene glycol dimethyl ether T=160°C; 0.333333 h; microwave irradiatuon; Product distribution / selectivity;

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: With n-butyllithium; diisopropylamine in tetrahydrofuran; hexanes T=-78 - 0°C; 1.5 h; 2: With iodine in tetrahydrofuran; hexanes T=-78°C; 0.333333 h;