Iodoethane → (3S)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898222노트

반응식

HRID 898222 반응식
[CH2:1]([C@@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:23])[CH:10]=2)[NH:5][C:4]1=[O:24])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH3:39]>CC(C)=O>[CH2:38]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([F:23])=[CH:8][CH:7]=2)[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@@H:3]([CH2:1][CH3:2])[C:4]1=[O:24])[CH3:39]

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69223582(3S)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

생성물 1

HCID 69222645(3S)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one수율 75%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
51 °C

실험 절차

To a stirred solution of (3S)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (0.25 g, 0.76 mmol) in acetone (6 mL) under nitrogen was added cesium carbonate (0.133 g, 0.41 mmol), potassium carbonate (0.057 g, 0.41 mmol) and iodoethane (0.20 mL, 0.39 g, 2.5 mmol). The reaction was stirred at 51° C. for 4 h. The solvent was evaporated, and the residue was partitioned between methylene chloride and water. The organic layer was separated and washed with water. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The product was purified via Biotage Horizon® (SiO2, gradient from 4% EtOAc/hexane to 38% EtOAc/hexane) to yield 0.19 g (75%) of (3S)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one. MS (ESI) m/z 357 ([M+H]+).

후처리

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe product was purified via Biotage Horizon® (SiO2, gradient from 4% EtOAc/hexane to 38% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-cf21503581eb46188be3a7521397a30e
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07351709B2

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