Cesium carbonate → 5-Chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-oxo-morpholin-3-yl)-pyridin-2-yl]-amide

Temperatur

80 °C

A mixture of 4,5-Bis(diphenyl phosphino)-9,9-dimethyl xanthene (0.04 g, 0.069 mmol), tris(dibenzylidene-acetone) di palladium(0) (0.032 g, 0.035 mmol) and cesium carbonate (0.678 g, 2.083 mmol) were taken in 1,4-dioxane and degassed with argon for 10 min. 5-(6-Bromo-pyridin-2-yl)-5-fluoromethyl-morpholin-3-one (0.2 g, 0.694 mmol) followed by 5-chloropicolinamide (0.119 g, 0.764 mmol) were added to the resultant reaction mixture and degassed with argon for further 5 min. Reaction mixture was then heated at 80° C. for 16 h and cooled to rt. Reaction contents were treated with water and product was extracted with ethyl acetate, washed with brine and dried over anhy. Na2SO4. The organic layer was concentrated under reduced pressure to obtain liquid which was triturated with n-pentane to furnish title compound as a off-white solid. Yield=0.24 g (crude). TLC (50% ethyl acetate in hexane) Rf=0.45; LCMS: RtH8=1.215, [M+1]=365.1 and 366.9; HPLC RtH9=4.367 min (53

1. customdegassed with argon for 10 min
2. additionwere added to the resultant
3. customreaction mixture
4. customdegassed with argon for further 5 min
5. customReaction mixture
6. temperaturecooled to rt
7. customReaction contents
8. extractionwas extracted with ethyl acetate
9. washwashed with brine
10. customdried over anhy
11. concentrationThe organic layer was concentrated under reduced pressure
12. customto obtain liquid which
13. customwas triturated with n-pentane

ORD-Eintrag

ord-0547882ffb2e4556b2333fbdc5dfa877

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08637508B2