6-chloro-N-methyl-3-pyridinesulfonamide synthesis

Yield:52480-30-5 0.429 g

Reaction Conditions:

with triethylamine in tetrahydrofuran;dichloromethane at 20; for 0.25 h;

Steps:

15.1 STEP 1 : 6-CHLORO-N-METHYL-3-PYRIDINESULFONAMIDE

A 100-mL round-bottomed flask was charged with 6-chloro-3- pyridinesulfonyl chloride (0.526 g, 2.48 mmol, Organic Process Research & Development 2009, 13, 875), TEA (1.04 mL, 7.45 mmol), and DCM (10 mL). Methylamine (2.0 M solution in THF, 1.30 mL, 2.60 mmol, Sigma- Aldrich, St. Louis, MO) was added dropwise at room temperature. The mixture was stirred at rt for 15 min. The reaction mixture was partitioned between water (30 mL) and DCM (30 mL). The aqueous phase was extracted with DCM (30 mL). The combined organic phases were washed with saturated aqueous sodium chloride (50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under a vacuum. The crude product was purified by column chromatography (50 g of silica, 0 to 60% EtOAc in hexanes) to afford 6-chloro- N-methyl-3-pyridinesulfonamide (0.429 g) as a white solid.

References:

WO2014/35872,2014,A1 Location in patent:Page/Page column 140-141