반응 #157824

반응 방정식

Water

3-(Difluoromethoxy)-6-iodo-2-[(4-methoxybenzyl)oxy]pyridine

cesium fluoride

(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(tributylstannyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

→

(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-(difluoromethoxy)-6-[(4-methoxybenzyl)oxy]-pyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

용매

ethyl acetate

N,N-dimethylformamide

반응 조건

후처리

1. 1
   여과After filtration through celite
2. 2
   세척the organic layer was washed with brine
3. 3
   건조The organic layer dried over anhydrous magnesium sulfate
4. 4
   여과filtered
5. 5
   기타after which the solvent was evaporated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→1:1)

실험 절차

3-(Difluoromethoxy)-6-iodo-2-[(4-methoxybenzyl)oxy]pyridine obtained in Reference Example 4-34 (727 mg), cesium fluoride (270 mg), copper iodide (187 mg) and tetrakis(triphenylphosphine)palladium (103 mg) were added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(tributylstannyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one obtained in Reference Example 4-26 (609 mg) in N,N-dimethylformamide (6 mL), and the mixture was stirred at 75° C. for two hours. Water and ethyl acetate were added to the reaction solution. After filtration through celite, the organic layer was washed with brine. The organic layer dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→1:1) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-(difluoromethoxy)-6-[(4-methoxybenzyl)oxy]-pyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless gum (511 mg).

출처