1: 95 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature 2: 1) n-BuLi, B(OMe)3, 2) Na2CO3 / 2) Pd(PPh3)4 / 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H2O, toluene, reflux, 24 h View Scheme

pyridine 1 h; Heating;

n-butyllithium; boric acid trimethyl ester; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H2O, toluene, reflux, 24 h; Yield given. Multistep reaction;

1: 100 percent / SOCl2 / 4 h / Heating 2: 100 percent / pyridine / 1 h / Heating View Scheme

sulfuric acid