Sodium Iodide → N-(3,5-dibromopyrazin-2-yl)-2-iodoacetamide

To a solution of 2-chloro-N-(3,5-dibromopyrazin-2-yl)acetamide (3.0 g, 9.11 mmol) in acetone (40 mL) was added sodium iodide (13.65 g, 91 mmol) dissolved in acetone (20 mL). Solution was allowed to stir at ambient temperature for 16 h. Solution was condensed under reduced pressure and diluted with ethyl acetate (500 mL) and washed consecutively with water (5×) to remove the blue color. Organics were dried over magnesium sulfate, filtered and solvent removed under reduced pressure to afford the crude product. The solid was diluted with 10% ethyl acetate in hexanes (40 mL) and sonicated while scraping the sides of the flask. The solution was then heated under a heat gun for 5 min, then cooled while sonicating at ambient temperature. The resulting solid was filtered and washed with additional hexanes and dried under vacuum to afford the title compound (3.0 g, 7.13 mmol, 78% yield). MS (ESI) m/z 420.3 [M−1]+, 422.0 [M+1]+, 424.0 [M+3]+.

1. customcondensed under reduced pressure
2. washwashed consecutively with water (5×)
3. customto remove the blue color
4. dry with materialOrganics were dried over magnesium sulfate
5. filtrationfiltered
6. customsolvent removed under reduced pressure
7. customto afford the crude product
8. customsonicated
9. temperatureThe solution was then heated under a heat gun for 5 min
10. temperaturecooled
11. customwhile sonicating at ambient temperature
12. filtrationThe resulting solid was filtered
13. washwashed with additional hexanes
14. customdried under vacuum

ORD record

ord-f277296fd1dd4f3093f16496ae85cd9f

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569494B2