1,4-Butanediol → 5-bromo-4-chloro-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-benzenesulfonamide

Temperature

50 °C

To a solution of 1,4-butanediol (0.315 mL, 3.6 mmol) in DMF (2.5 mL) at ambient temperature was added sodium hydride (60%, 34 mg, 0.85 mmol) and the mixture was stirred for 15 minutes. A solution of 5-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamide (0.268 g, 0.71 mmol) in DMF (2.5 mL) was added and the mixture heated at 50° C. for 2 h. The solvent was removed in vacuo and water and DCM were added. The mixture was extracted with DCM. The organic layer was washed with brine and was dried over anhydrous MgSO4. Concentration of the filtrate provided a residue that was purified by silica gel chromatography [eluent: 50% ethyl acetate in hexane] to afford 5-bromo-4-chloro-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-benzenesulfonamide as a solid (0.309 g). MS: 451.0 (M+H)+; tR=2.59 min (method 1).

1. customThe solvent was removed in vacuo and water and DCM
2. additionwere added
3. extractionThe mixture was extracted with DCM
4. washThe organic layer was washed with brine
5. dry with materialwas dried over anhydrous MgSO4
6. customConcentration of the filtrate provided a residue that
7. customwas purified by silica gel chromatography [eluent: 50% ethyl acetate in hexane]

ORD record

ord-663c6000ddc741a292521aeb4fe61ebc

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263588B2