Hydrochloric Acid → N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

5-Bromo-2-chloro-3-pyridinamine (10 g) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.5 ml) was added and stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at RT for 5 h. Further methanesulfonyl chloride (2.1 ml) was added and the mixture stirred at RT overnight. The ph was adjusted to ˜6 by the addition of 2M HCl (aq). The mixture was then extracted with DCM (2×150 ml) and the combined organic layers were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M NaOH (50 ml) was added. The mixture was stirred for 1 hour and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and washed with DCM (150 ml). The aqueous layer was then acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give title compound (13.45 g) as an off white solid.

1. stirringthe reaction stirred at RT for 5 h
2. stirringthe mixture stirred at RT overnight
3. extractionThe mixture was then extracted with DCM (2×150 ml)
4. customthe solvent removed in vacuo
5. addition2M NaOH (50 ml) was added
6. stirringThe mixture was stirred for 1 hour
7. customthe solvent removed in vacuo
8. dissolutionThe residue was dissolved in water (250 ml)
9. washwashed with DCM (150 ml)
10. filtrationthe resulting precipitate collected by filtration
11. customdried overnight

ORD record

ord-d04162c08e9b4505817d39761d6e5a97

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163743B2