sodium hydroxide; polyaniline-supported palladium in water T=100°C; Suzuki coupling; 6 h;

1.1: potassium phosphate; palladium diacetate; triphenylphosphine / toluene / 16 h / 100 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 18 h / -15 - 20 °C 2.2: 20 °C View Scheme

di-tert-butylphosphine; (2,6-iPr2-C6H3OCO-N)-imidazolium-(N-CH2C6H4-2-Br) bromide; caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0) in 1,4-dioxane T=150°C; Suzuki-Miyaura coupling; 48 h;

1: 6-chloro-nicotinic acid With tritylchloride-polystyrene resin; N-ethyl-N,N-diisopropylamine in dichloromethane; N,N-dimethyl-formamide T=20°C; 18 h; 2: 2,4-dimethoxybenzeneboronic acid With potassium phosphate; phenyl-phospha-adamantane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in tetrahydrofuran; water T=20°C; solid-phase Suzuki coupling; 15 h; 3: With trifluoroacetic acid in dichloromethane T=20°C; 1.5 h; Further stages.;

1: 7-methoxy-4H-chromen-4-one With 1,10-phenanthroline; oxygen; palladium diacetate in N,N-dimethyl-formamide Heck type reaction; 0.0833333 h; 2: 2,4-dimethoxybenzeneboronic acid in N,N-dimethyl-formamide T=100°C; Heck type reaction; 24 h; regioselective reaction;

sodium carbonate in ethanol; ethyl acetate; toluene

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in tetrahydrofuran T=80°C; 18 h; Inert atmosphereReflux;

1: 4-oxo-4H-1-benzopyran With 1,10-phenanthroline; oxygen; palladium diacetate in N,N-dimethyl-formamide Heck type reaction; 0.0833333 h; 2: 2,4-dimethoxybenzeneboronic acid in N,N-dimethyl-formamide T=100°C; Heck type reaction; 24 h; regioselective reaction;

1.1: 88 percent / Na2CO3; LiCl / [Pd(PPh3)4] / 1,2-dimethoxy-ethane; H2O / 80 °C 2.1: LDA / tetrahydrofuran; hexane / -78 °C 2.2: 79 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 73 percent / PtCl2 / toluene / 80 °C 4.1: 79 percent / H2 / Pd/C / ethyl acetate / 760 Torr View Scheme