tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethylene glycol dimethyl ether T=90°C; Suzuki coupling; 1 h;

1: 3-Methylpyridine With n-butyllithium; 2-(dimethylamino)-ethanol in hexane T=0°C; 1.5 h; 2: With tributyltin chloride in tetrahydrofuran; hexane T=-78°C; 1 h; 3: 3-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine in xylene Stille coupling reaction; 12 h; Heating;

1.1: n-BuLi / toluene; hexane; tetrahydrofuran / -50 °C 1.2: triisopropyl borate / toluene; tetrahydrofuran; hexane / -50 - -15 °C 1.3: 73 percent / aq. NaOH / toluene; tetrahydrofuran; hexane 2.1: 76 percent / Pd(PPh3)4; aq. Na2CO3 / 1,2-dimethoxy-ethane / 1 h / 90 °C View Scheme