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ChemicalBook CAS DataBase List 5-FLUORO-2-METHYL-3-PYRIDINECARBOXALDEHYDE
959616-51-4

5-FLUORO-2-METHYL-3-PYRIDINECARBOXALDEHYDE synthesis

4synthesis methods
3-Pyridinemethanol, 5-fluoro-2-methyl-

959616-50-3
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5-FLUORO-2-METHYL-3-PYRIDINECARBOXALDEHYDE

959616-51-4
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-

Yield:-

Reaction Conditions:

Stage #1:(5-fluoro-2-methylpyridin-3-yl) methanol with 4-methylmorpholine N-oxide in dichloromethane at 20; for 0.5 h;Molecular sieve;
Stage #2: with tetrapropylammonium perruthennate in dichloromethane at 20; for 1.5 h;

Steps:

103
To a solution of 32 mg of (5-fluoro-2-methylpyridin-3-yl) methanol in 2 mL of dichloromethane, 80 mg of molecular sieves 3A and 40 mg of 4-methylmorpholine N-oxide were added, and the mixture was stirred at room temperature for 30 minutes. Thereto was added 6.0 mg of tetrapropyl ammonium perruthenate, and the mixture was stirred at room temperature for 1 hour 30 minutes. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol = 100:1 to obtain 20 mg of 5-fluoro-2-methylnicotinaldehyde as a colorless oily substance. 1H-NMR (CDCl3) δ: 2.87 (3H, d, J = 1.0 Hz), 7.81 (1H, dd, J = 8.0, 3.0 Hz), 8.56 (1H, d, J = 3.0 Hz), 10.33 (1H, d, J = 2.2 Hz)

References:

TOYAMA CHEMICAL CO., LTD.;Taisho Pharmaceutical Co. Ltd. EP2022793, 2009, A1 Location in patent:Page/Page column 67