pyridine hydrochloride 0.25 h;

1: 1) n-BuLi / 1) THF, hexane, -75 deg C, 1.5 h, 2) THF, -75 deg C, 1 h 2: 84 percent / pyridinium chloride / 0.25 h / 210 °C View Scheme

1: 1) n-BuLi / 1) THF, hexane, -75 deg C, 1.5 h, 2) THF, -75 deg C, 1 h 2: 79 percent / pyridinium chloride / 0.25 h / 210 °C View Scheme

1: 1) n-BuLi, 2) I2 / 1) THF, hexane, -75 deg C, 1.5 h, 2) THF, -75 deg C, 1 h 2: 1) K2CO3 / 2) Pd(PPh3)4 / 1) EtOH, toluene, 2) reflux 3: 86 percent / pyridinium chloride / 0.25 h / 210 °C View Scheme

1: 1) n-BuLi / 1) THF, hexane, -75 deg C, 1.5 h, 2) THF, -75 deg C, 1 h 2: 78 percent / pyridinium chloride / 0.25 h / 210 °C View Scheme