1: 2-bromo-6-methyl-pyridine With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.25 h; 2: With zinc(II) chloride in tetrahydrofuran; hexane T=20°C; 0.5 h; 3: methyl 2-chloro-6-methyl-pyridine-4-carboxylate With diisobutylaluminium hydride; PdCl2-(PPh3)2 in tetrahydrofuran; hexane Negishi cross-coupling reaction; 1.5 h; Heating; Further stages.;

bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; copper(l) iodide in N,N-dimethyl-formamide T=100°C; Suzuki-Miyaura cross-coupling; 6 h; Inert atmosphere;

1: 2-bromo-6-methyl-pyridine With n-butyllithium; tributyltin chloride in tetrahydrofuran; hexane T=-78 - 20°C; 2: 4-carbomethoxy-6-methyl-2-(trifluoromethanesulfonyloxy)pyridine With triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride in xylene Stille-type cross-coupling; 24 h; Heating;

1: 2-bromo-6-methyl-pyridine With n-butyllithium; tributyltin chloride in tetrahydrofuran; hexane T=-78 - 20°C; 2: methyl 2-methyl-6-lt;(p-toluenesulfonyl)oxygt;pyridine-4-carboxylate With triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride in xylene Stille-type cross-coupling; 24 h; Heating;

1: 2-bromo-6-methyl-pyridine With n-butyllithium; tributyltin chloride in tetrahydrofuran; hexane T=-78 - 20°C; 2: 4-carbomethoxy-6-methyl-2-(methanesulfonyloxy)pyridine With triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride in xylene Stille-type cross-coupling; 24 h; Heating;

tetrakis(triphenylphosphine) palladium(0) in toluene Stille coupling; 24 h; Inert atmosphereReflux;

1.1: 85 percent / Et3N / CH2Cl2 / 8 h / 60 °C 2.1: n-BuLi; Bu3SnCl / tetrahydrofuran; hexane / -78 - 20 °C 2.2: PPh3 / PdCl2(PPh3)2 / xylene / 24 h / Heating View Scheme

1.1: 92 percent / aq. HCl / 6 h / Heating 2.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: ZnCl2 / hexane; tetrahydrofuran / 0.5 h / 20 °C 2.3: 84 percent / DIBAH / PdCl2-(PPh3)2 / hexane; tetrahydrofuran / 1.5 h / Heating View Scheme