Ethyl Acetate → Ethyl 3-(5-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-2-fluorophenyl)propanoate

HRID 709702노트

반응식

HRID 709702 반응식
Cl[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:6]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:5][CH:4]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:25]=1[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C>[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:7]1[N:8]=[C:3]([CH2:2][O:30][C:27]2[CH:28]=[CH:29][C:24]([F:23])=[C:25]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:26]=2)[CH:4]=[CH:5][C:6]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[F:22]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 68536248Ethyl 3-(2'-fluoro-5'-hydroxyphenyl)propionateHCID 1177599996-(Chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine

생성물 1

HCID 117759865Ethyl 3-(5-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-2-fluorophenyl)propanoate수율 81.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 6-(chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine (380 mg) in acetonitrile (10 mL) were added ethyl 3-(2-fluoro-5-hydroxyphenyl)propanoate (300 mg) and cesium carbonate (650 mg), and the mixture was heated under reflux for 15 hr. Ethyl acetate was added to the reaction mixture, and the insoluble material was filtered off. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (480 mg) as a colorless oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. filtrationthe insoluble material was filtered off
  4. customThe solvent in the filtrate was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3a248489f28645aea88bd0eab434a6c8
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181186B2

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