반응 #591178

반응 방정식

Water

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

sodium carbonate

3-thiopheneboronic acid

→

5-(1,3-dioxolan-2-yl)-8-methoxy-1-(6-thiophen-3-ylpyridin-3-ylmethyl)-3,4-dihydro-1H-quinolin-2-one

수율 99.8%

용매

ethyl acetate

1,2-dimethoxyethane

반응 조건

후처리

1. 1
   온도by heating
2. 2
   온도under reflux in an argon atmosphere for 4 hours
3. 3
   세척The extract was washed twice with water
4. 4
   세척washed with a saturated sodium chloride solution
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)
9. 9
   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), tetrakis(triphenylphosphine)palladium (0.12 g) and a 2N aqueous solution of sodium carbonate (2.5 ml) were suspended in 8 ml of 1,2-dimethoxyethane, and 0.20 g of 3-thiopheneboronic acid was added, followed by heating under reflux in an argon atmosphere for 4 hours. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1). 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-thiophen-3-ylpyridin-3-ylmethyl)-3,4-dihydro-1H-quinolin-2-one as a light brown amorphous solid.

출처