Methanesulfonyl chloride → HCID 86700398, compound

Temperature

0 °C

A stirring solution of the 1-(4-bromopyridin-2-yl)ethanol (3.72 g, 18.41 mmol and DMAP (4.5 g, 36.82 mmol) in 75 mL of dichloromethane was cooled to 0° C. To it was added mesyl chloride (1.71 mL, 22.09 mmol) dropwise. The mixture was stirred at 0° C. for 10 minutes, then warmed to room temperature and stirred for 15 min. The reaction was quenched with 50 mL ice water, the layers were separated, and the aqueous layer was extracted with dichloromethane (50 mL). The organics were combined, washed with water and brine, dried over Na2SO4, and purified by column chromatography (gradient 0 to 45% EtOAc/hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.40 (d, J=5.3 Hz, 1H), 7.64 (d, J=1.6 Hz, 1H), 7.45 (dd, J=5.3, 1.8 Hz, 1H), 5.75 (q, J=6.6 Hz, 1H), 3.00 (s, 3H), 1.75 (d, J=6.6 Hz, 3H).

1. temperaturewarmed to room temperature
2. stirringstirred for 15 min
3. customThe reaction was quenched with 50 mL ice water
4. customthe layers were separated
5. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
6. washwashed with water and brine
7. dry with materialdried over Na2SO4
8. custompurified by column chromatography (gradient 0 to 45% EtOAc/hexanes)
9. customto afford the product

ORD record

ord-cbce090ffcf742a68acc4e8ca31ede98

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987250B2