Chlorosuccinimide → 4-Bromo-5-chloropyridin-2-amine

To a solution of 4-bromopyridin-2-amine (500 mg, 2.89 mmol) in N,N-dimethylformamide (5 mL) was added N-chlorosuccinimide (463 mg, 3.47 mmol) and the mixture was stirred at room temperature for 12 hours. The mixture was filtered through diatomaceous earth and concentrated and the residue was dissolved in ethyl acetate. The solution was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude title compound. Purification by column chromatography (silica gel, 30% ethyl acetate in hexane) afforded the title compound.

1. filtrationThe mixture was filtered through diatomaceous earth
2. concentrationconcentrated
3. dissolutionthe residue was dissolved in ethyl acetate
4. washThe solution was washed with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto afford the crude title compound
9. customPurification by column chromatography (silica gel, 30% ethyl acetate in hexane)

ORD record

ord-d14e4019191643db9bdf739666e4969a

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073922B2