Reaktion #67061

Reaktionsgleichung

4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine

methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate

(R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

cesium carbonate

→

methyl 1-[5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydroquinoline-6-carboxylate

Ausbeute 55.8%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturwith reflux for 1 hour
3. 3
   Extraktionthe aqueous layer was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Vorschrift

A mixture of 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine (200 mg), methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate (323 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (25 mg), cesium carbonate (661 mg), and toluene (3 mL) was heated with reflux for 1 hour. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain methyl 1-[5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydroquinoline-6-carboxylate (170 mg) as a yellowish white solid.

Quelle