Triethylamine → N-(2-Chloro-5-iodopyridin-4-yl)-N-(methylsulfonyl)methanesulfonamide

4-Amino-2-chloro-5-iodopyridine (11) (1.01 g, 3.97 mmol) was dissolved in dichloromethane (8.5 mL) and triethylamine (2.48 mL, 1.78 g 17.6 mmol) was added. The suspension was cooled in an ice/water bath. A solution of methanesulfonyl chloride (1.56 mL, 2.31 g, 20.1 mmol) in dichloromethane (4.2 mL) was added dropwise. The reaction was stirred at room temperature for 100 min. More triethylamine (1.25 mL) was added to the reaction, which was then cooled in ice. To the cooled reaction was added dropwise a solution of methanesulfonyl chloride (0.78 mL, 1.15 g, 10 mmol) in dichloromethane (2.1 mL) and stirring at room temperature was continued for 16 h. The reaction was diluted with dichloromethane and washed twice with water. The residue was purified by flash chromatography eluting with dichloromethane, then 5% ethyl acetate in dichloromethane to give the title compound (13) (1.188 g 72%). 1H-NMR (500 MHz, DMSO-d6): 3.69 (s, 6H), 8.03 (s, 1H), 8.99 (s, 1H).

1. temperatureThe suspension was cooled in an ice/water bath
2. temperaturewas then cooled in ice
3. customTo the cooled reaction
4. stirringstirring at room temperature
5. waitwas continued for 16 h
6. washwashed twice with water
7. customThe residue was purified by flash chromatography
8. washeluting with dichloromethane

ORD record

ord-20ff9682856c49ffb26ae76920bff803

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371319B2