sulfuric acid in water 3 h; Heating;

1.1: n-BuLi; TMEDA / tetrahydrofuran / 2.25 h / -70 - -10 °C 1.2: 45 percent / 1,2-dibromoethane / tetrahydrofuran / 2.25 h / -70 - -10 °C 2.1: 76 percent / KOH / methanol / 4 h / Heating View Scheme

dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; tris-(dibenzylideneacetone)dipalladium(0); K3PO4*3H2O

hydrogen bromide Ambient temperatureIrradiation;

1: acetophenone With allyl(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene)palladium(IV) chloride; sodium hexamethyldisilazane in tetrahydrofuran T=20°C; 0.0833333 h; Inert atmosphere; 2: 3-amino-4-bromopyridine in tetrahydrofuran T=20 - 100°C; 4 h; Inert atmosphere; regioselective reaction;

1: 53 percent / t-BuONa; 1,1'-bis(diphenylphosphino)ferrocine / Pd2(dba)3 / toluene / 17 h / 100 °C 2: 61 percent / Na2CO3 / Pd(OAc)2 / dimethylformamide / Heating View Scheme

copper(l) iodide; N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide in 1,4-dioxane T=110°C; 24 h;