Sodium Iodide → 5-Ethyl-2-pyridinol
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C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][N:4]=1.[Na+].[I-].C[Si](Cl)(C)C>CO.[Pd]>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3](=[O:2])[NH:4][CH:5]=1)[CH3:10]C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][N:4]=1.[Na+].[I-].C[Si](Cl)(C)C>CO.[Pd]>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3](=[O:2])[NH:4][CH:5]=1)[CH3:10]To a solution of 2-methoxy-5-vinyl-pyridine (2 g) in anhydrous MeOH was added Pd/C (10 wt %, 100 mg). The mixture was stirred under H2 atmosphere for 5 hours before it was filtered through a pad of celite. The solvent was removed in vacuo and the residue was taken directly into next step without further purification. The crude product from previous step was dissolved in anhydrous MeCN. To this solution was added NaI (3.3 g, 21.9 mmol) and TMSCl (2.8 mL, 21.9 mmol). The resulting mixture was heated to 65° C. for 5 hours before it was filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography to afford the desired product (1.5 g, 83% yield). 1H NMR (300 MHz, CDCl3): δ 1.17 (t, J=7.5 Hz, 3 H), 2.39-2.49 (m, 2 H), 6.50-6.58 (m, 1 H), 7.15 (s, 1 H), 7.35-7.45 (m, 1 H).
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