Sodium hydride → N-(3-Chloro-4-(4-methylpyridin-3-yl)phenyl)methanesulfonamide

Participants

Reaction Steps

To a solution of Intermediate 27 (0.102 g, 0.466 mmol) and methanesulfonyl chloride (0.043 mL, 0.560 mmol) in DMF (3.26 mL) was added sodium hydride (0.037 g, 0.933 mmol) at room temperature. The reaction mixture was allowed to stir at room temperature for 3 days, then quenched with saturated aqueous NH4Cl solution and diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (5×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford a yellow residue, which was further dried under high vacuum. The crude material was dissolved in CH2Cl2 and purified by silica gel chromatography using an ISCO machine (12 g column, 30 mL/min, 0-10% MeOH in CH2Cl2 over 25 min, tr=14 min) to afford the title compound (5.1 mg, 0.016 mmol, 3.54% yield) as a white solid.

Provenance & Evidence