Dimethylamine → 6-Bromo-N,N-dimethyl-2-pyridinesulfonamide

2,6-Dibromopyridine (12 g, 50 mmol) was dissolved in diethyl ether (150 mL) and the solution was cooled to −70° C. n-Butyl lithium (1.6M in hexane, 35 mL, 55 mmol) was added slowly and the solution was stirred for 15 minutes. Sulfur dioxide gas was then passed through the mixture until a pale yellow precipitate was produced. The reaction mixture was then warmed to room temperature and the solvent was evaporated under reduced pressure. The resulting residue was triturated with petroleum ether to afford the intermediate. The salt was then suspended in dichloromethane, cooled to −70° C. and sulfuryl chloride (75 mL, 93 mmol) was added slowly. The reaction mixture was stirred for 75 minutes and dimethylamine was then added until a basic pH was achieved. The mixture was washed with water and the organic solution was dried over magnesium sulfate and concentrated in vacuo. Trituration of the residue with dichloromethane and petroleum ether afforded the title compound as a white solid in 38% yield, 5.1 g

1. additionwas added slowly
2. customwas produced
3. customthe solvent was evaporated under reduced pressure
4. customThe resulting residue was triturated with petroleum ether
5. customto afford the intermediate
6. temperaturecooled to −70° C.
7. stirringThe reaction mixture was stirred for 75 minutes
8. washThe mixture was washed with water
9. dry with materialthe organic solution was dried over magnesium sulfate
10. concentrationconcentrated in vacuo

ORD record

ord-d51c2eef9bf0458e9ce66faa81eaa9d8

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557121B2