1: 3-Methyl-6-bromo-1H-indazole With sodium hydride in tetrahydrofuran; paraffin oil (nujol) T=0°C; 0.166667 h; 2: methyl iodide in tetrahydrofuran; paraffin oil (nujol) T=20°C; 12 h;

ammonium acetate 144 h; Heating / reflux;

1.1: diethyl ether / 12 h / 20 °C / Cooling with ice 2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 12 h / 20 °C 3.1: hydrazine hydrate / ethylene glycol / 12 h / 165 °C 4.1: sodium hydride / tetrahydrofuran; paraffin oil (nujol) / 0.17 h / 0 °C 4.2: 12 h / 20 °C View Scheme

1.1: hydrazine hydrate / ethylene glycol / 12 h / 165 °C 2.1: sodium hydride / tetrahydrofuran; paraffin oil (nujol) / 0.17 h / 0 °C 2.2: 12 h / 20 °C View Scheme

1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: hydrazine hydrate / ethylene glycol / 12 h / 165 °C 3.1: sodium hydride / tetrahydrofuran; paraffin oil (nujol) / 0.17 h / 0 °C 3.2: 12 h / 20 °C View Scheme