Water → Ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968067노트

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HRID 1968067 반응식
[F:1][C:2]1[CH:19]=[CH:18][C:5](/[CH:6]=[N:7]/[C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][O:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[CH:20]([C:22]1[CH:32]=[CH:31][C:25]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[CH:24][CH:23]=1)=O.[O-:33][CH2:34][CH3:35].[Na+].O>C(OCC)(=O)CC.CCOC(C)=O>[CH3:29][N:28]([CH3:30])[C:26]([C:25]1[CH:31]=[CH:32][C:22]([CH:20]2[C:34](=[O:33])[C:35]3[C:13]([C:12]([O:11][CH2:10][CH3:9])=[O:17])=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][CH:6]2[C:5]2[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:23][CH:24]=1)=[O:27]

참가 물질

7

반응물 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 105592054-formyl-N,N-dimethylbenzamideHCID 178519076HCID 178519076, 화합물

생성물 1

HCID 67261670Ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate수율 44%

시약·촉매·용매 2

HCID 7749Ethyl Propionate용매HCID 8857Ethyl Acetate용매

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온도
30 °C

실험 절차

Sodium (115 mg, 5 mmol) was added to EtOH (10 mL) to afford sodium ethoxide. (E)-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (500 mg, 1.96 mmol) and 4-formyl-N,N-dimethylbenzamide (382 mg, 2.16 mmol) were dissolved in ethyl propionate (10 mL), and the sodium ethoxide solution was added dropwise to the mixture at 0° C., then the mixture were heated to 30° C. for 1 h. To the reaction mixture was added water and EtOAc, the organic phase was separated, washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and then concentrated to afford the crude product. The crude product was purified by flash chromatography (MeOH:DCM 1:25) to give the title compound (400 mg, yield 44%). LC-MS (ESI) m/z: 461 (M+1)+

후처리

  1. customthe organic phase was separated
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customThe crude product was purified by flash chromatography (MeOH:DCM 1:25)

출처 및 근거

ORD 기록
ord-bbace241b0cb42d0a24b854d8e1f546f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420650B2

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