1,4-Dioxane → 5-Bromo-3-ethylpyridin-2-amine

To a solution prepared by dissolving 360 mg of 3-ethylpyridine-2-amine (synthesized according to the method disclosed in International Publication WO2006/025567, page 142) in a mixed solvent of 12 mL of 1,4-dioxane and 4 mL of water, 553 mg of N-bromosuccinimide was added at 0° C., and the mixture was stirred for 1.5 hours at the same temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer thus obtained was washed with water and saturated brine in that order, and dried over anhydrous sodium sulfate. Thereafter, the insolubles were filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=75/25), to obtain 394 mg of 5-bromo-3-ethylpyridine-2-amine [33-1] (hereinafter, referred to as the compound [33-1]).

1. customTo a solution prepared
2. customsynthesized
3. additionwas added at 0° C.
4. extractionwas extracted with ethyl acetate
5. customThe organic layer thus obtained
6. washwas washed with water and saturated brine in that order
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThereafter, the insolubles were filtered
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=75/25)

ORD record

ord-7c45c7211b7f4808b0c0721ac565b9fe

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977336B2