3-BroMo-5fluoro-4-Methylpyridine

Step 1 : To a solution of LDA (2M solution in Cy/ethylbenzole THF, 21.3 mL, 42.6 mmol) in dry THF (23 mL) was added dropwise over 10 min a solution of 3-bromo-5-fluoropyridine (5.0 g, 28.4 mmol) in dry THF (23 mL) at -78°C and stirring continued at -78°C for 30 min. Subsequently a solution of CHStep 1 A solution of diisopropylamine (1.9 mL, 13.7 mmol) in 20 mL of THF is cooled to 0°C and treated with n-butyllithium (6.7 mL, 13.6 mmol). The mixture is stined at 0°C for 15 minutes then cooled to -78°C. 3-Bromo-5-fluoropyridine (2.0 g, 11.4 mmol) is added drop-wise as a solution in 20 mL of THF. This mixture is stined at -78°C for 45 minutes. A separate solution of iodomethane (2.1 mL, 34.1 mmol) in 20 mL of THF is cooled to -78°C. The anion solution is then cannulated into the iodomethane solution. Once the transfer is complete, the mixture is stirred at -78°C for 30 minutes. The cooling bath is removed and the mixture is stined for 30 minutes and then quenched with saturated NH4C1 solution. The mixture is diluted with EtOAc and water. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated. The residue is purified via silica gel flash column chromatography eluting with 0-10 percent EtOAc/heptane to afford 1.4 g of the title compound.