1: With toluene-4-sulfonic acid in water; acetonitrile T=60 - 65°C; 4 h; 2: With pyridine in water; acetonitrile T=20°C; 3.16667 h;

1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / toluene; 1,4-dioxane / 8 h / 99 °C / |Inert atmosphere 2: anhydrous potassium trimethylsilanolate / N,N-dimethyl-formamide; tetrahydrofuran / 1.67 h / 20 - 25 °C / |Inert atmosphere 3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 - 50 °C 4: N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 50 °C / |Inert atmosphere 5: phosphoric acid; water / acetonitrile / 6.25 h / 20 - 53 °C View Scheme

caesium carbonate; palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in toluene T=50°C; 29 h; Heating / reflux;

1: 6-amino-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester With copper(l) iodide in isopropyl alcohol T=40°C; 0.25 h; 2: With potassium carbonate; ethylene glycol 1 h; Heating / reflux; 3: 4-bromo-2-chloro-1-iodo-benzene With isopropyl alcohol 26 h;