lithium diisopropyl amide in tetrahydrofuran 1.) -75 deg C, 1 h, 2.) -75 deg C, 2 h;

1: 2-fluoro-4-iodo-pyridine With lithium diisopropyl amide in tetrahydrofuran 2: methyl halide in tetrahydrofuran

1: 1.) n-BuLi / 1.) THF, -78 deg C 2: 74 percent / NBS, DBP / CCl4 3: 96 percent / butan-2-one / 0.25 h / Heating 4: NaOH / H2O 5: 3N HCl / 21 h / Heating View Scheme

1: 1) n-BuLi / 1) THF, -78 deg C, 1 min, 2) THF, -78 deg C, 15 min 2: 84 percent / pyridinium chlorochromate, 4 Angstroem molecular sieves, Celite / CH2Cl2 / 1) 0 deg C -> room temperature, 2) room temperature, 29 h 3: 92 percent / HCl, air / H2O / 2 h / Heating 4: 1) t-BuOK / 1) DME, THF, room temperature, 30 min, 2) DME, THF, reflux, 4 d 5: 57 percent / CH3COOK, Bu4NBr, Pd(CH3COO)2 / acetonitrile / 3 h / Heating View Scheme