sodium hydroxide in ethanol; water T=0 - 20°C; 4 h;

amberlyst-15 resin T=90°C; Microwave irradiationNeat (no solvent);

indium monobromide in tetrahydrofuran 14 h; Heating;

sodium hydroxide in methanol T=20°C;

sodium hydride 1) THF, 1.5 h, room temperature; 2) THF, 1.1 h, room temperature, reflux, 3 h, room temperature, overnight; Yield given. Multistep reaction;

1: sodium tetrahydroborate / methanol / 1 h / 0 °C 2: sodium acetate; toluene-4-sulfonic acid hydrazide / tetrahydrofuran; water / Reflux 3: 2-aminopyridine; copper(l) iodide; sodium methylate / diethylene glycol dimethyl ether / 24 h / 100 °C View Scheme