Methyl iodide → HCID 66793909, compound

Participants

Reaction Steps

To a solution of 5-bromo-pyridine-3-sulfonic acid dimethylamide (CAS #896160-99-9, 100 mg, 0.377 mmol) in THF (3.8 mL) at −78° C. was added lithium diisopropylamide (0.5 M solution in THF, 0.85 mL, 0.42 mmol). The reaction was stirred for 15 minutes, at which time iodomethane (0.030 mL, 0.48 mmol) was added. The reaction was stirred for an additional 15 minutes and was then quenched with saturated aqueous ammonium chloride. Next, the reaction was diluted with water, dichloromethane, and saturated aqueous sodium bicarbonate. The layers were separated and aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by semi-preparative reverse phase HPLC (20 to 90% acetonitrile/water w/0.1% NH4OH) to furnish 5-bromo-4-methyl-pyridine-3-sulfonic acid dimethylamide; MS: (ES+) m/z 279.0 (M+H)+.

Provenance & Evidence