potassium carbonate; potassium iodide in N,N-dimethyl acetamide T=0 - 45°C; 3 h;

1: 5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole; N-alkylation of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate With tert-butylamine hydrobromide; potassium carbonate in acetone T=0 - 55°C; 32 h; 2: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl bromide With potassium carbonate; potassium iodide in acetone T=20 - 55°C; 3 h;

potassium carbonate; potassium iodide in N,N-dimethyl acetamide T=0 - 45°C; 3 h; Inert atmosphere;

potassium carbonate; potassium iodide in acetone T=50 - 55°C; 3 h;

N-ethyl-N,N-diisopropylamine in N,N-dimethyl acetamide T=40 - 65°C; 5 h; Product distribution / selectivity;

potassium carbonate in N,N-dimethyl acetamide

sodium carbonate in N,N-dimethyl acetamide T=45 - 50°C; Large scale reaction;

1.1: potassium carbonate / toluene / 0.75 h / 45 - 50 °C 1.2: 10 h / 60 - 70 °C 2.1: diisopropylamine; sodium hydroxide / toluene; isobutyramide / 4 h / 25 - 45 °C 2.2: 8 h / 40 - 70 °C 2.3: 25 - 35 °C / pH ~ 6 - 7 View Scheme

1.1: potassium carbonate / toluene / 0.75 h / 45 - 50 °C 1.2: 10 h / 60 - 70 °C 2.1: diisopropylamine; sodium hydroxide / toluene; isobutyramide / 4 h / 25 - 45 °C 2.2: 8 h / 40 - 70 °C 2.3: 25 - 35 °C / pH ~ 6 - 7 View Scheme

1: N-alkylation of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate With potassium carbonate in water; toluene T=45 - 65°C; 0.916667 h; Industry scale; 2: [2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl bromide With tetrabutylammomium bromide T=60 - 70°C; 10 h; Industry scale; 3: medoxomil chloride Product distribution / selectivity;