in N,N-dimethyl-formamide T=70 - 80°C; Vilsmeier-Haack Formylation; 6 h;

potassium phosphate; tetrakis(triphenylphosphine) palladium(0); potassium bromide in 1,4-dioxane Suzuki-Miyaura cross-coupling reaction; 1 h; Inert atmosphereReflux;

1: N,N-dimethyl-formamide With trichlorophosphate T=0 - 5°C; 0.5 h; 2: C14H13ClN2 in N,N-dimethyl-formamide T=50°C; 3 h;

1.1: acetic acid; sodium hydroxide / ethanol / 1 h / Reflux 2.1: trichlorophosphate / 0.5 h / 0 - 5 °C 2.2: 3 h / 50 °C View Scheme

1.1: acetic acid; sodium hydroxide / ethanol / 1 h / Reflux 2.1: trichlorophosphate / 0.5 h / 0 - 5 °C 2.2: 3 h / 50 °C View Scheme

1.1: bromine / chloroform / 20 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere 2.2: 1 h / 60 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / toluene / 48 h / 20 °C 5.1: triethylamine / dichloromethane / 1 h / 20 °C 6.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0); potassium bromide / 1,4-dioxane / 1 h / Inert atmosphere; Reflux View Scheme

1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C / Inert atmosphere 2: trifluoroacetic acid / toluene / 48 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 20 °C 4: potassium phosphate; tetrakis(triphenylphosphine) palladium(0); potassium bromide / 1,4-dioxane / 1 h / Inert atmosphere; Reflux View Scheme

1: trifluoroacetic acid / toluene / 48 h / 20 °C 2: triethylamine / dichloromethane / 1 h / 20 °C 3: potassium phosphate; tetrakis(triphenylphosphine) palladium(0); potassium bromide / 1,4-dioxane / 1 h / Inert atmosphere; Reflux View Scheme

1: trichlorophosphate / 12 h / -10 - 70 °C 2: trifluoroacetic acid / toluene / 48 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 20 °C 4: potassium phosphate; tetrakis(triphenylphosphine) palladium(0); potassium bromide / 1,4-dioxane / 1 h / Inert atmosphere; Reflux View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere 1.2: 1 h / 60 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / toluene / 48 h / 20 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0); potassium bromide / 1,4-dioxane / 1 h / Inert atmosphere; Reflux View Scheme