sodium chlorite; 2-methyl-but-2-ene; acetic acid in water; acetonitrile T=20 - 30°C; 2 h; Cooling with ice; Reagent/catalyst;

1: 4-Amino-3,5-dichloropyridine With cesium fluoride in dimethyl sulfoxide T=90°C; 3 h; 2: (3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-imidazol-1-yl)methanone in dimethyl sulfoxide T=90 - 95°C; 6.5 h; Reagent/catalyst;

sodium hydride in tetrahydrofuran T=0°C; 0.5 h;

1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With thionyl chloride in toluene Heating / reflux; 2: 4-Amino-3,5-dichloropyridine With sodium hydride in tetrahydrofuran 1 h; Cooling;

in DMF (N,N-dimethyl-formamide) T=15 - 40°C;

1.1: aminosulfonic acid; sodium chlorite / water; acetonitrile / 5 h / 0 - 20 °C 2.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 3 h / |Reflux 3.1: sodium hydroxide / toluene / 2 h 3.2: 6 h / |Reflux View Scheme

1.1: potassium carbonate; potassium iodide / acetone / 0.5 h / |Inert atmosphere; |Reflux 1.2: 12.5 h / 20 °C / |Inert atmosphere; |Reflux 2.1: aminosulfonic acid; sodium chlorite / water; acetonitrile / 5 h / 0 - 20 °C 3.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 3 h / |Reflux 4.1: sodium hydroxide / toluene / 2 h 4.2: 6 h / |Reflux View Scheme

Large scale;

1: thionyl chloride / 3 h / 50 °C 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / |Large scale 3: potassium hydroxide; copper(l) iodide; 8-hydroxy-quinoline / dimethyl sulfoxide / 30 h / 100 °C / |Inert atmosphere; |Large scale 4: thionyl chloride / 3 h / 50 °C 5: potassium carbonate / N,N-dimethyl-formamide / 1.25 h / 95 °C 6: sodium hydroxide / methanol / 3 h / 50 °C 7: |Large scale View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / |Large scale 2: potassium hydroxide; copper(l) iodide; 8-hydroxy-quinoline / dimethyl sulfoxide / 30 h / 100 °C / |Inert atmosphere; |Large scale 3: thionyl chloride / 3 h / 50 °C 4: potassium carbonate / N,N-dimethyl-formamide / 1.25 h / 95 °C 5: sodium hydroxide / methanol / 3 h / 50 °C 6: |Large scale View Scheme