Cesium carbonate → Ethyl 3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)-4-methylphenyl)propanoate

HRID 709663노트

반응식

HRID 709663 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.[OH:23][C:24]1[CH:25]=[C:26]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:27]=[CH:28][C:29]=1[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:22][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=1[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][O:23][C:24]2[CH:25]=[C:26]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:27]=[CH:28][C:29]=2[CH3:30])=[N:8][C:7]=1[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 117759964Ethyl 3-(3-hydroxy-4-methylphenyl)propanoateHCID 1177599996-(Chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine

생성물 1

HCID 117760300Ethyl 3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)-4-methylphenyl)propanoate수율 88.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 6-(chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine (350 mg) in acetonitrile (30 ml) were added ethyl 3-(3-hydroxy-4-methylphenyl)propanoate (191 mg) and cesium carbonate (597 mg), and the mixture was heated under reflux for 15 hr. The reaction mixture was concentrated, and water was added to the residue. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (400 mg) as a yellow oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe extract was washed with saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-180c9ecd96164a4f9f934ed9cd1af282
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181186B2

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