Pyridine → N-(4-Ethynylphenyl)methanesulfonamide

Participants

Reaction Steps

step 1—To a solution of 4-ethynyl aniline (4.00 g, 34.00 mmol) DCM (60 mL) at 0° C. was added sequentially pyridine (3.32 mL, 40.8 mmol) and dropwise addition of methanesulfonyl chloride (3.17 mL, 40.80 mmol). The reaction was stirred and allowed to warm from 0° C. to RT over 3 h then poured into a saturated aqueous NaHCO3 (150 mL). The aqueous layer was separated and extracted with DCM (2×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with 20% EtOAc/hexanes to afford 5.92 g (88%) of N-(4-ethynyl-phenyl)-methanesulfonamide (80) as a solid.

Provenance & Evidence