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With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; water; ethyl acetate;
Step 1 6-Ethyl-2-pyridinecarboxaldehyde To a solution of N,N,N-trimethylethylenediamine (4.29 mL, 33 mmol) in THF (20 mL) at -25 C. was added n-BuLi (13.2 mL, 2.5M in hexanes, 33 mmol). This solution was stirred 15 minutes, then transferred into a -78 C. solution of 6-methyl-2-pyridine-carboxaldehyde (3.63 g, 30 mmol) in THF (80 mL). After stirring 30 minutes at -78 C., a THF (50 mL) solution of lithium diisopropylamide (33 mmol) was added and the now dark red mixture was stirred 1 hour at -78 C. Methyl iodide (5.68 g, 40 mmol) in THF (10 mL) was added and reaction mixture was allowed to warm to r.t. for 4 hours. Water and 25% aq. NH4 OAc were added, the crude product was extracted with EtOAc (2*) and solvents were evaporated. Purification by flash chromatography (from 5% to 10% EtOAc in hexanes) gave 660 mg of the title compound.
Step 2 6-Isopropyl-2-pyridinecarboxaldehyde The alkylation of <strong>[153646-82-3]6-ethyl-2-pyridinecarboxaldehyde</strong> from Step 1 was performed as described above for 6-methyl,2-pyridinecarboxaldehyde. 1 H NMR (CD3 COCD3): delta 10.0 (1H, s), 7.93 (1H, t), 7.75 (1H, d), 7.57 (1H, d), 3.18 (1H, m), 1.32 (6H, d).
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