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Ethyl Acetate → Ethyl 1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

HRID 1428084
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HRID 1428084 반응식
CC1C=CC(S(O[CH2:12][CH2:13][F:14])(=O)=O)=CC=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23](=[O:33])[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][NH:26][CH:27]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[F:14][CH2:13][CH2:12][N:26]1[CH:27]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)[C:23](=[O:33])[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25]1
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

생성물 1

HCID 86700035Ethyl 1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate수율 29.8%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
80 °C

실험 절차

2-Fluoroethyl 4-methylbenzenesulfonate (1.00 g) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (1.00 g) and cesium carbonate (2.49 g) in DMF (9 ml) at room temperature. The reaction mixture was stirred at 80° C. for two hours. The reaction mixture was returned to room temperature and diluted by adding ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the residue was purified by silica gel column chromatography [ethyl acetate:hexane:methanol=1:1:0->7:3:0->1:0:0->19:0:1 (v/v)] to give 0.35 g of the title compound as an oily substance.

후처리

  1. customwas returned to room temperature
  2. additiondiluted
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [ethyl acetate:hexane:methanol=1:1:0->7:3:0->1:0:0->19:0:1 (v/v)]

출처 및 근거

ORD 기록
ord-9bc181e7c7004466a32dcb752ea23d18
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933103B2

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