Methyl iodide → 3,5-Dibromo-4-methylpyridine

A solution of dry diisopropylamine (11.0 g, 108 mmol) in dry THF under nitrogen was cooled with a −78° C. bath, and n-butyl lithium (2.50 M in hexane, 39 mL) was added. The reactant solution was warmed to ambient temperature, and then cooled to −78° C. again. A solution of 3,5-dibromopyridine (22 g, 93 mmol) in dry THF was added. After stirring at −78° C. for 30 min, CH3I (17 g, 120 mmol) was added, the mixture was warmed to ambient temperature and stirred over night. The reaction was quenched with water, extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated. The residue was purified by column chromatography to afford 3,5-dibromo-4-methylpyridine: 1H-NMR (400 MHz, CDCl3) ppm 8.55 (s, 2H), 2.55 (s, 3H);

1. temperaturecooled to −78° C. again
2. temperaturethe mixture was warmed to ambient temperature
3. stirringstirred over night
4. customThe reaction was quenched with water
5. extractionextracted with EtOAc
6. washthe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulphate
8. concentrationconcentrated
9. customThe residue was purified by column chromatography

ORD record

ord-601e16f3b0c44992922919611ded2daa

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206199B2