3-FORMYL-6-METHYL-PYRIDINE

B. B. To a solution of 5-bromo-2-methylpyridine (151; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at -78 Example 22. Synthesis of 2-(6-methylpyridin-3-yl)-N-(thiazol-2-yl)-[l, 2, 4]triazolo[l, 5- a]pyridine-8-carboxamide (Compound 210): Step 1) Preparation of 6-methylnicotinaldehyde (93): 9Step 1 To a solution of 5-bromo-2-methyl-pyridine (2.0 g, 11.6mmol) in anhydrous THF (20 mL) was added isopropylmagnesium chloride (2M in THF, 9.3 mL, 1.6 eq). dropwise over 30 mins at 0 °C under nitrogen atmosphere, then the reaction mixture was stirred at room temperature for 6 hrs. DMF (1.02 g, 1.2 eq) was added to the reation mixture at 0 °C for 30 mi amd the mixture was the stirred at room temperature for overnight. The reaction mixture was poured into water (50 mL), and the aqueous phase was extracted with EtOAc (50 mL x3). The extracts were washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuum to give 4.5 g of crude 6-methylpyridine-3-carbaldehyde as yellow oil.