1: 1.5 h / Heating 2: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 3: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 4: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 5: 91 percent / acetic acid / 0.67 h / 80 - 90 °C 6: 100 percent / trimethyltin azide / toluene / 29 h / Heating 7: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C View Scheme

1: 100 percent / trimethyltin azide / toluene / 29 h / Heating 2: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C View Scheme

1: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 2: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 3: 91 percent / acetic acid / 0.67 h / 80 - 90 °C 4: 100 percent / trimethyltin azide / toluene / 29 h / Heating 5: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C View Scheme

triethylamine in acetone T=55 - 60°C; 4 - 8 h; Product distribution / selectivity;

triethylamine in dichloromethane

triethylamine in methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide

1: tert-butyldimethylsilyl chloride; 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid With triethylamine in chloroform T=20°C; 3 h; 2: 1-(cyclohexyloxycarbonyloxy)ethyl chloride With triethylamine in chloroform 24 h;

1.1: triethylamine / dichloromethane / 3.75 h / 25 - 35 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 60 - 65 °C 3.1: formic acid; methanol / dichloromethane / 7 h / 30 - 35 °C 3.2: 0.33 h / 15 - 20 °C View Scheme

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