Dimethylformamide → HCID 59006385, compound

Temperature

80 °C

The mixture of 327 mg of 3-bromo-2-nitropyridine, 256.5 mg of dichlorobis(triphenylphosphine)palladium (II), 518 μL of tributyl(vinyl)tin, and 6 mL of N,N-dimethylformamide, was stirred at 80° C. for 3 hours. The reaction mixture was cooled back to room temperature, then 500 mg of potassium fluoride and 1.5 mL of water were added thereto, and stirred at room temperature for 30 minutes. The insolubles were filtered through celite, a saturated aqueous solution of sodium hydrogen carbonate was added, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the thus obtained residue was purified by silica gel column chromatography, to obtain 236 mg of 2-nitro-3-vinylpyridine [120-1] as a pale red solid.

1. temperatureThe reaction mixture was cooled back to room temperature
2. stirringstirred at room temperature for 30 minutes
3. filtrationThe insolubles were filtered through celite
4. additiona saturated aqueous solution of sodium hydrogen carbonate was added
5. extractionextracted with ethyl acetate
6. washThe obtained organic layer was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThe insolubles were filtered
9. concentrationthe filtrate was concentrated under reduced pressure
10. customthe thus obtained residue was purified by silica gel column chromatography

ORD record

ord-3c181475b53544a2b59307d00d7bf9fb

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718801B2