1: 1H-benzo[d]imidazole With sodium hydride in tetrahydrofuran T=60°C; 1 h; 2: propyl bromide in tetrahydrofuran T=60°C; 48 h;

1,10-phenanthroline; caesium carbonate; copper(I) bromide in N,N-dimethyl-formamide T=20 - 90°C; 16 h; Inert atmosphere;

sodium hydroxide T=60 - 70°C; 0.333333 h;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene 6 h; Heating;

1: 1.) sodium hydride / 1) acetonitrile, reflux, 1 h; 2) acetonitrile, reflux, 2 h 2: 1.) sodium borohydride / 1) ethanol, rt, 10 min; 2) ethanol, rt, 3 h 3: 89 percent Spectr. / Bu3SnH, AIBN / toluene / 6 h / Heating View Scheme

1: 86 percent / acetonitrile / 70 h / Heating 2: 94 percent / Na, EtOH / 0.08 h / Ambient temperature View Scheme

1: sodium hydroxide / methanol / 4 h / |Inert atmosphere; |Reflux 2: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran; acetonitrile / 0.67 h / 20 °C / |Inert atmosphere; |Darkness 3: camphor-10-sulfonic acid / acetonitrile / 6 h / |Reflux; |Irradiation; |Inert atmosphere View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 100 °C / |Inert atmosphere 1.2: 16 h / 20 °C / |Inert atmosphere 2.1: sodium hydroxide / methanol / 4 h / |Inert atmosphere; |Reflux 3.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran; acetonitrile / 0.67 h / 20 °C / |Inert atmosphere; |Darkness 4.1: camphor-10-sulfonic acid / acetonitrile / 6 h / |Reflux; |Irradiation; |Inert atmosphere View Scheme

in tetrahydrofuran T=65°C;

potassium hydroxide; sodium tetrahydroborate; bis(benzonitrile)palladium(II) dichloride; HN(CH2COOMe)2; 3-chloro-benzenecarboperoxoic acid 1.) THF; Yield givenMultistep reaction;