Triethylamine → 5-Ethenylpyridin-2-amine

Vinyltributyltin (13 mL, 44.6 mmol), palladium(II) acetate (0.45 g, 2.1 mmol), triethylamine (12.4 mL, 89.1 mmol) and tri-(o-tolyl)phosphine (3.69 g, 12.15 mmol) were added to a solution of 5-bromopyridin-2-amine (7.0 g, 40.5 mmol) in acetonitrile (70 mL) and the reaction mixture refluxed for 18 hours. The reaction mixture was washed with 2M sodium carbonate solution (80 mL), the organics separated, dried over magnesium sulphate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using methanol:dichloromethane 3:97 to yield 3.6 g of product. This residue was dissolved in dichloromethane and washed with aqueous solutions of potassium fluoride and then sodium hydrogencarbonate. The organic solution was dried over magnesium sulphate, filtered and concentrated in vacuo to yield 1.9 g of final product.

1. temperaturethe reaction mixture refluxed for 18 hours
2. washThe reaction mixture was washed with 2M sodium carbonate solution (80 mL)
3. dry with materialthe organics separated, dried over magnesium sulphate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe crude product was purified by column chromatography on silica gel

ORD record

ord-1748d3059dbe49f992c3a7d8243c37fb

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262192B2