potassium hydroxide in water; N,N-dimethyl-formamide T=35°C; Ullmann Condensation; 12 h; Inert atmosphere;

potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); biphenyl-2-yl-di-tert-butyl-phosphane in N,N-dimethyl-formamide T=100°C; 12 h; Inert atmosphere;

potassium fluoride; mono(bis(di-tert-butyl(4-(dimethylamino)phenyl)phosphonio)palladium(II))dichloride; water in N,N-dimethyl-formamide T=90°C; 12 h; Inert atmosphere;

1: 1-(2-bromopyridine-5-yl)-2,5-dimethyl-1H-pyrrole With tert.-butyl lithium in tetrahydrofuran; pentane T=-78°C; Negishi coupling reaction; 2: With zinc(II) chloride in tetrahydrofuran; pentane T=20°C; 3: 2-chloro-5-(trifluoromethyl)-pyridine With Pd0(tris(tert-butyl)phosphine)2 in tetrahydrofuran; pentane Heating; Title compound not separated from byproducts;

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; sodium formate; palladium on activated charcoal in water; ethylene glycol; toluene Heating; Further byproducts given;

1.1: pTsOH / toluene / 2 h / Heating 2.1: tBuLi / tetrahydrofuran; pentane / -78 °C 2.2: ZnCl2 / tetrahydrofuran; pentane / 20 °C 2.3: [Pd(tBu3P)2] / tetrahydrofuran; pentane / Heating View Scheme