반응 #1148619

반응 방정식

ethanol

sodium carbonate

bis(triphenylphosphin)paradium

2,3-dimethylpyridine

ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

→

ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate

용매

toluene

Ethyl acetate

반응 조건

후처리

1. 1
   온도under an argon atmosphere, the resulting mixture was heated
2. 2
   온도under reflux for 4 hours
3. 3
   기타the organic layer was separated
4. 4
   세척rinsed with water
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   기타The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1)

실험 절차

226.8 mg of ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (XIII) was suspended in 3 ml of toluene, and 1.6 ml of ethanol, 0.82 ml of a 2M sodium carbonate solution, 311.1 mg of (+)-1-methyl-2-tritylisoindoline-5-boric acid (3) and 23.2 mg of bis(triphenylphosphin)paradium (II) chloride were added thereto, and thereafter, under an argon atmosphere, the resulting mixture was heated under reflux for 4 hours. Ethyl acetate was added to the reaction solution and the organic layer was separated and rinsed with water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1) to obtain 335.9 mg of ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (XIV).

출처