Tetrahydrofuran → Ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)propanoate

Temperatur

65 °C

A mixture of ethyl 2-(2-chloropyridin-4-yl)propanoate (51) (1.55 g, 7.25 mmol), tert-butylcarbamate (2.55 g, 21.76 mmol), Pd2 dba3 (0.166 g, 0.181 mmol), caesium carbonate (3.55 g, 10.88 mmol) and Xantphos (0.210 g, 0.363 mmol) in THF (10 mL) was purged with nitrogen and heated at 65° C. for 48 hr. The mixture was then cooled to RT, diluted with water and extracted with ether. The ether layer was washed with water and brine and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution) to afford the title compound (52) (1.35 g, 61%): m/z 295 (M+H)+ (ES+).

1. customwas purged with nitrogen
2. temperatureThe mixture was then cooled to RT
3. additiondiluted with water
4. extractionextracted with ether
5. washThe ether layer was washed with water and brine
6. dry with materialdried (MgSO4)
7. customevaporated in vacuo
8. customThe residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution)

ORD-Eintrag

ord-663ab8ce6d8147fdbdd8d3baf21496f6

Quelldatensatz

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08299073B2