N-bromobutanimide → 2-Amino-5-bromo-4-chloropyridine

Temperature

26.5 °C

To a stirred solution of 2-amino-4-chloropyridine (1 g) in acetonitrile (8 mL) was added dropwise a solution of N-bromosuccinimide (1.5 g) in acetonitrile (2 mL). The reaction mixture was stirred at 25-28° C. for 1 h. The solvent was evaporated, then the residue was suspended in water and extracted with dichloromethane (2×20 mL). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under vacuum. The resulting crude material was purified by column chromatography, using 100-200 mesh size silica and 10-25% EtOAc in hexane as eluent, to give the title compound (1 g) as a yellow solid. δH (400 MHz, CDCl3) 8.16 (s, 1H), 6.62 (s, 1H), 4.55 (br s, 2H). LCMS: m/z 208.9, RT 2.19 minutes.

1. customThe solvent was evaporated
2. extractionextracted with dichloromethane (2×20 mL)
3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customThe resulting crude material was purified by column chromatography

ORD record

ord-6748200609424c89b2de26bf527696cb

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309243B2