ammonium cerium (IV) nitrate in methanol 1 h;

1: bromobenzene With magnesium in diethyl ether 1 h; Heating; 2: N-methoxy-N-methyl-1H-indazole-3-carboxamide in diethyl ether 0.166667 h; Heating;

in tetrahydrofuran T=-84 - 20°C;

tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 4 h; Inert atmosphere;

1: bromobenzene With magnesium in diethyl ether 1 h; Heating; 2: tert-butyl 3-{[methoxy(methyl)amino]carbonyl}-1H-indazole-1-carboxylate in diethyl ether 0.166667 h; Heating;

tetrabutyl ammonium fluoride; copper(I) bromide in tetrahydrofuran; dichloromethane T=20°C; 4 h; Inert atmosphere;

1.1: pyridine / tetrahydrofuran / 2.5 h / 0 - 20 °C 1.2: 84 percent / pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 20 °C 2.1: magnesium / diethyl ether / 1 h / Heating 2.2: 92 percent / diethyl ether / 0.17 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -84 °C 1.2: 5 percent / tetrahydrofuran; hexane / -84 - 20 °C 2.1: magnesium / diethyl ether / 1 h / Heating 2.2: 92 percent / diethyl ether / 0.17 h / Heating View Scheme

1.1: hydrogenchloride; sodium nitrite / acetonitrile; water / 0 - 5 °C 1.2: 1 h / 0 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); pyrrolidine / 60 °C / |Inert atmosphere 2.2: 10.5 h / 60 °C / |Inert atmosphere 3.1: copper (II) acetate monohydrate; oxygen / methanol / 90 °C / |Schlenk technique 4.1: ammonium cerium (IV) nitrate / methanol / 1 h View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0); pyrrolidine / 60 °C / |Inert atmosphere 1.2: 10.5 h / 60 °C / |Inert atmosphere 2.1: copper (II) acetate monohydrate; oxygen / methanol / 90 °C / |Schlenk technique 3.1: ammonium cerium (IV) nitrate / methanol / 1 h View Scheme