Methyl iodide → 3-Bromo-4-(methoxymethyl)pyridine

Participants

Reaction Steps

To an ice-cold solution of Intermediate 65A (1.0 g, 5.32 mmol) in THF (Volume: 26.6 ml) was added sodium hydride (0.255 g, 6.38 mmol). The ice bath was removed and the reaction mixture was allowed to stir at room temperature for 30 min, then cooled to 0° C. and followed by addition of methyl iodide (0.366 ml, 5.85 mmol). The ice bath was removed and the reaction mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was then quenched with water and concentrated to remove the THF. The resulting aqueous layer was extracted with DCM (3×). The combined organics were washed with water and brine, dried, and concentrated to give an oil. The oil was purified by silica gel chromatography (hexane: ethyl acetate 70:30) to afforded the title compound as a colorless oil. MS (ES): m/z=203.9 [M+H]+. Intermediate 65 was used in the synthesis of Example 254.

Provenance & Evidence