caesium carbonate in 1,4-dioxane; methanol T=100°C; Suzuki coupling; 24 h; Inert atmosphere;

1: iodine; potassium hydroxide / N,N-dimethyl-formamide / 0.75 h / 20 °C 2: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0.5 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 4: caesium carbonate / 1,4-dioxane; methanol / 24 h / 100 °C / Inert atmosphere View Scheme

1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0.5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 3: caesium carbonate / 1,4-dioxane; methanol / 24 h / 100 °C / Inert atmosphere View Scheme

1: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 2: caesium carbonate / 1,4-dioxane; methanol / 24 h / 100 °C / Inert atmosphere View Scheme