반응 #620580

반응 방정식

methyl 4-bromo-3-chloroquinoline-6-carboxylate

2,4-difluorophenylboric acid

cesium fluoride

1,4-dioxane

→

methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate

수율 69.3%

용매

water

water

반응 조건

후처리

1. 1
   기타was returned to room temperature
2. 2
   추출extracted with ethyl acetate
3. 3
   농축The organic layer was concentrated under reduced pressure
4. 4
   기타the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

실험 절차

Under argon gas atmosphere, a mixture of methyl 4-bromo-3-chloroquinoline-6-carboxylate (130 mg), 2,4-difluorophenylboric acid (137 mg), a 1,1′-bis(diphenylphosphino)ferrocene palladium (H) dichloride/dichloromethane complex (177 mg), cesium fluoride (197 mg), 1,4-dioxane (8 mL), and water (2 mL) was heated under stirring in an oil bath at 100° C. for one day. The reaction mixture was returned to room temperature, and water was added, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate (100 mg).

출처