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

HRID 898247노트

반응식

HRID 898247 반응식
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[NH:10][C:9](=[O:18])[C@H:8]1[CH2:19][CH3:20])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:34][CH3:35]>C(#N)C>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[N:10]([CH2:34][CH3:35])[C:9](=[O:18])[C@H:8]1[CH2:19][CH3:20])=[O:6]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 69221283(3R)-4-(2,4-dimethoxybenzoyl)-3-ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one

생성물 1

HCID 69220797(3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one수율 71%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
89 °C

실험 절차

To a stirred solution of (3R)-4-(2,4-dimethoxybenzoyl)-3-ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one (0.25 g, 0.73 mmol) in acetonitrile (6 mL) under nitrogen was added cesium carbonate (0.24 g, 0.74 mmol) and iodoethane (0.19 mL, 0.37 g, 2.4 mmol). The mixture was stirred at 89° C. in a sealed tube for 12 h. The solvent was evaporated, and the residue was partitioned between water and methylene chloride. The layers were separated, and the organic layer was washed twice with water, dried over magnesium sulfate, concentrated in vacuo, and purified via Biotage Horizon® (SiO2, gradient from 7% EtOAc/hexane to 51% EtOAc/hexane) to yield 0.20 g (71%) of (3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one.

후처리

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between water and methylene chloride
  3. customThe layers were separated
  4. washthe organic layer was washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified via Biotage Horizon® (SiO2, gradient from 7% EtOAc/hexane to 51% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-25493bf928c44efcaf7312b16f6447e8
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07351709B2

반응 노트

불러오는 중…