Methyl Acrylate → HCID 10749820, compound

Temperature

100 °C

2-Amino-5-bromopyridine (13.5 g, 78.0 mmol), methyl acrylate (10.1 g, 117 mmol) and tris(2-methylphenyl)phosphine (4.75 g, 15.6 mmol) were dissolved in acetonitrile (200 mL), palladium(II) acetate (1.75 g, 7.8 mmol) was added and the mixture was stirred overnight under an argon atmosphere at 100° C. After cooling the reaction mixture, the insoluble material was removed by filtering through celite and the solvent was evaporated under reduced pressure. The residue was dissolved in saturated aqueous sodium hydrogencarbonate and chloroform, and he mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform, then 0%-5% methanol/ethyl acetate), and recrystallized from ethyl acetate-hexane to give the title compound (3.81 g, yield 27%) as yellow crystals.

1. temperatureAfter cooling the reaction mixture
2. customthe insoluble material was removed
3. filtrationby filtering through celite
4. customthe solvent was evaporated under reduced pressure
5. dissolutionThe residue was dissolved in saturated aqueous sodium hydrogencarbonate
6. extractionchloroform, and he mixture was extracted with ethyl acetate
7. washThe organic layer was washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (chloroform
11. custom0%-5% methanol/ethyl acetate), and recrystallized from ethyl acetate-hexane

ORD record

ord-7ae1a47279d945098dd1524896d3262e

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2