1: tert.-butyl lithium; carbon tetrabromide / -78 °C 2: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine; potassium phosphate / 1,4-dioxane / 1 h / 120 °C / |Inert atmosphere; |Microwave irradiation 3: hydrogenchloride / tetrahydrofuran / 20 °C / |Inert atmosphere View Scheme

1: 1H-imidazo[4,5-b]-pyridine With sodium hydride in N,N-dimethyl-formamide T=20°C; 2: methyl iodide in N,N-dimethyl-formamide T=50°C;

3,4,5,6-tetramethyl-t-Bu-X-Phos; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate in tert-butyl alcohol T=110°C; 4 h; Inert atmosphere;

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere 3.1: 3,4,5,6-tetramethyl-t-Bu-X-Phos; potassium phosphate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / tert-butyl alcohol / 4 h / 110 °C / Inert atmosphere View Scheme

T=120°C; 24 h; Inert atmosphere;

1: tetrahydrofuran / 20 °C / |Inert atmosphere 2: acetic acid; iron / 3 h / 90 °C / |Inert atmosphere 3: 24 h / 120 °C / |Inert atmosphere View Scheme

1: tetrafluoroboric acid / toluene / 120 °C / |Inert atmosphere 2: tetrahydrofuran / 20 °C / |Inert atmosphere 3: acetic acid; iron / 3 h / 90 °C / |Inert atmosphere 4: 24 h / 120 °C / |Inert atmosphere View Scheme