Dimethyl Sulfate → Methyl 4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylate

Participants

Reaction Steps

The product of Example 21, Step 1 (3.0 g, 9.056 mmol, 1.0 equiv) was dissolved in 100 mL DMF and NaH (725 mg, 18.11 mmol, 2.0 equiv) was added slowly to the reaction mixture. Me2SO4 (1.72 mL, 18.11 mmol, 2.0 equiv) was added and the reaction was stirred at room temperature for 45 min. The reaction was quenched with water and diluted with EtOAc. After the phases were separated, the organic phase was washed once with satd. NaHCO3 and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was triturated with Et2O and filtered to provide 1.5 g (48%) of the title compound as a light yellow solid. MS (ES+) m/e 346 [M+H]+

Provenance & Evidence