Ethyl Acrylate → HCID 68105235, compound

A N,N-dimethylformamide suspension (406 ml) of 2,5-dichloropyridine-3-amine (81.2 g), palladium acetate (11.2 g), 1,4-bis(diphenylphosphino)butane (42.5 g), ethyl acrylate (109 ml), diisopropylethylamine (174 ml) and tetrabutylammonium bromide (161 g) was stirred at 140° C. for 30 hours. After the reaction solution was brought back to room temperature, ethyl acetate and water were added and the solution was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue was added a 50% ethyl acetate-hexane mixed solvent, followed by stirring. The insolubles were filtered off, and washed with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford ethyl (2E)-3-(3-amino-5-chloropyridin-2-yl)acrylate (50.6 g).

1. customwas brought back to room temperature
2. customthe solution was separated
3. extractionthe aqueous layer was extracted with ethyl acetate
4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. additionTo the residue was added a 50% ethyl acetate-hexane mixed solvent
7. filtrationThe insolubles were filtered off
8. washwashed with ethyl acetate
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-9d5f5b49df52407db5e4bca0320c6087

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729095B2