N-bromobutanimide → HCID 90421671, compound

Temperature

0 °C

To a solution of Intermediate (6-fluoro-pyridin-2-yl)-dimethyl-amine (12.4 g, 88.4 mmol) in acetonitrile (400 mL) at 0° C. was added a solution of N-bromosuccinimide (7.87 g, 44.2 mmol) in acetonitrile (95 mL) dropwise over 15 min. The resulting solution was stirred at 0° C. for 1 hour. Another portion of N-bromosuccinimide (7.87 g, 44.2 mmol) in acetonitrile (95 mL) was subsequently added at 0° C. dropwise over 15 min. The solution was slowly warmed to room temperature and stirred overnight. The solution was concentrated in vacuo and diluted with dichloromethane (500 mL). This was washed with water (300 mL) and the aqueous layer back extracted with dichloromethane (3×200 mL), before drying over MgSO4, filtering, and concentrating in vacuo. The material was passed through a silica pad, eluting with 0-10% ethyl acetate in heptanes. The organics were concentrated in vacuo to afford desired material (18.4 g, 95% yield) that solidified upon standing. 1H NMR (CDCl3, 400 MHz) 5=7.48-7.67 (m, 1 H) 6.21 (dd, J=8.59, 1.56 Hz, 1 H) 3.05 (s, 6 H); MS (FID)=218.0 (M)+.

1. temperatureThe solution was slowly warmed to room temperature
2. stirringstirred overnight
3. concentrationThe solution was concentrated in vacuo
4. additiondiluted with dichloromethane (500 mL)
5. washThis was washed with water (300 mL)
6. extractionthe aqueous layer back extracted with dichloromethane (3×200 mL)
7. dry with materialbefore drying over MgSO4
8. filtrationfiltering
9. concentrationconcentrating in vacuo
10. washeluting with 0-10% ethyl acetate in heptanes
11. concentrationThe organics were concentrated in vacuo

ORD record

ord-75b417e219d64677b00605f671afd074

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2