Methyl iodide → N-((5-Bromopyridin-3-yl)methyl)-N-methylethanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (0.21 g, 0.752 mmol), prepared as described in Example 11a, in DMF (6 mL) at −10° C., was added sodium hydride (60% oil dispersion, 39 mg, 0.98 mmol). The reaction was stirred for 15 minutes at which time iodomethane (0.056 ml, 0.903 mmol) dissolved in DMF (1 mL) was added. The reaction was stirred at −10° C. for an additional 15 minutes and was then quenched with ammonia hydroxide (2 mL). The reaction was diluted with brine and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate, 0 to 80%) to provide ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-methyl-amide; MS: (ES+) m/z 293.1 (M+H)+.

Provenance & Evidence