반응 #591176

반응 방정식

N-methylaniline

1-(6-Chloropyridin-3-ylmethyl)-5-[1,3]dioxolan-2-yl-8-methoxy-3,4-dihydro-1H-quinolin-2-one

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

sodium tert-butoxide

→

5-(1,3-dioxolan-2-yl)-8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-3,4-dihydro-1H-quinolin-2-one

수율 95.0%

용매

toluene

반응 조건

후처리

1. 1
   온도the resulting mixture was heated
2. 2
   온도under reflux in an argon atmosphere for 13 hours
3. 3
   농축After concentration under reduced pressure
4. 4
   기타the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→dichloromethane:methanol=20:1)
5. 5
   농축The purified product was concentrated under reduced pressure

실험 절차

1-(6-Chloropyridin-3-ylmethyl)-5-[1,3]dioxolan-2-yl-8-methoxy-3,4-dihydro-1H-quinolin-2-one (0.4 g), tris(dibenzylideneacetone)dipalladium (48.8 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (92.6 mg) and sodium tert-butoxide (0.15 g) were suspended in toluene (10.6 ml). N-methylaniline (0.17 g) was added, and the resulting mixture was heated under reflux in an argon atmosphere for 13 hours. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→dichloromethane:methanol=20:1). The purified product was concentrated under reduced pressure to thereby obtain 0.45 g (yield: 95%) of 5-(1,3-dioxolan-2-yl)-8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-3,4-dihydro-1H-quinolin-2-one as an amorphous solid.

출처