sodium azide; copper diacetate in N,N-dimethyl-formamide T=120°C; 12 h;

trimethylsilylazide; tetrabutyl ammonium fluoride T=120°C; 36 h;

Zinc chloride in (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide

1: 1-Bromo(1H-tetrazol-5-yl)benzene With zinc trifluoromethanesulfonate in acetonitrile 24 h; Heating; 2: p-methylphenylboronic acid With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in ethylene glycol dimethyl ether; water Suzuki reaction; 24 h; Heatingsolid phase synthesis; 3: With trifluoroacetic acid in dichloromethane 4 h; Further stages.;

1: para-bromotoluene With magnesium in tetrahydrofuran T=50°C; 1 h; 2: 5-(2-fluorophenyl)-1H-tetrazole in tetrahydrofuran; ethylene glycol dimethyl ether T=80°C; Grignard reaction; 12 h;

sodium azide in acetic acid

in ethylene glycol dimethyl ether 16 h; Heating;

1.1: TEA; NaN3 / toluene 2.1: Mg / tetrahydrofuran / 1 h / 50 °C 2.2: 93 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / 12 h / 80 °C View Scheme

1.1: palladium dichloride / methanol; toluene / 0.17 h / 20 °C / |Inert atmosphere 1.2: 12 h / 110 °C / |Inert atmosphere 2.1: zinc(II) chloride; sodium azide / N,N-dimethyl-formamide / 48 h / 120 °C View Scheme

1.1: palladium dichloride / methanol; toluene / 0.17 h / 20 °C / |Inert atmosphere 1.2: 12 h / 110 °C / |Inert atmosphere 2.1: zinc(II) chloride; sodium azide / N,N-dimethyl-formamide / 48 h / 120 °C View Scheme