Methyl iodide → ethyl 5-(2-fluoro-4-(2-methoxy-4,6-dimethylpyridin-3-yl)phenyl)-1-[(3RS,4SR)-4-methoxytetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate

Participants

Reaction Steps

Sodium hydride (60% oil dispersion, 86 mg) was added to a solution of ethyl 5-(2-fluoro-4-(2-methoxy-4,6-dimethylpyridin-3-yl)phenyl)-1-[(3RS,4SR)-4-hydroxytetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate (612 mg) in THF (5 mL) under ice-cooling, followed by stirring for three minutes. Methyl iodide (0.142 mL) was added to the reaction mixture, and the mixture was stirred at the same temperature for five minutes, and then warmed to room temperature and stirred for further two hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 27% to 48%) to give the title compound (379 mg).

Provenance & Evidence