n-butyllithium in tetrahydrofuran; hexane under Ar; addn. of hexane soln. of n-BuLi to 2-bromo-4-picoline in THF at -78°C, after 0.5 h Bu3SnCl added, stirred at -78°C (monitored by TLC), warmed to room temp., addn. of a satd. aq. soln. of NH4Cl; org. phase sepd., aq. phase extracted with Et2O, combined org. layers washed with brine, dried over Na2SO4, evapn. under vac., chromy. (Al2O3, EtOAc/hexane (1/20));

1: 4-Methylpyridine With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: tributyltin chloride in tetrahydrofuran; hexane T=-78 - 20°C;

tetrakis(triphenylphosphine) palladium(0) in toluene Stille-type cross-coupling; 48 h; Heating;

tetrakis(triphenylphosphine) palladium(0) in toluene T=110°C; Substitution; Stille reaction; 16 h;

tetrakis(triphenylphosphine) palladium(0) in toluene 72 h; Inert atmosphereReflux;

tetrakis(triphenylphosphine) palladium(0) in toluene T=120°C;