Hydrochloric Acid → 5-fluoro-3-iodo-1-methyl-1H-pyridin-2-one

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Reaction Steps

To 5-fluoro-3-iodo-pyridin-2-ol (31, 200 g, 838 mmol) in 3000 mL of acetone was cooled in an ice water bath. Cesium carbonate (354 g, 1088 mmol) was added, then iodomethane (58.1 mL, 929 mmol) was added dropwise over 30 minutes. The reaction was stirred overnight at room temperature. The reaction was concentrated under vacuum and the resulting material partitioned between ethyl acetate and water. The aqueous layer was isolated and adjusted to pH 3-4 with 3 N hydrochloric acid, then extracted with ethyl acetate. The combined organic layers were concentrated under vacuum to provide the desired compound as an off white solid. (32, 150 g, 593 mmol, 70.8%).

Provenance & Evidence