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

HRID 898229ノート

反応式

HRID 898229 の反応式
[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-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:38][CH3:39]>C(#N)C>[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]

参加物

6

反応物 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69223657(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

生成物 1

HCID 69221429(3R)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one収率 96.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (0.20 g, 0.61 mmol) in acetonitrile (5 mL) under nitrogen was added potassium carbonate (0.050 g, 0.36 mmol), cesium carbonate (0.11 g, 0.33 mmol) and iodoethane (0.15 mL, 0.29 g, 1.9 mmol). The reaction was stirred for 10 h at 50° C. and then 5 h at 63° C. The solvent was evaporated, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with water. The organic layer was concentrated in vacuo and purified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 33% EtOAc/hexane) to yield 0.21 g (96%) of (3R)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one. MS (ESI) m/z 357 ([M+H]+); HRMS: calcd for C20H21FN2O3, 356.16090; found (ESI+), 357.16057.

後処理

  1. custom5 h
  2. customat 63° C
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. concentrationThe organic layer was concentrated in vacuo
  8. custompurified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 33% EtOAc/hexane)

出典と根拠

ORDレコード
ord-dbf43c6a8c704971853871ea2f93ad39
出典データセット
uspto-grants-2008_04
特許番号
US07351709B2

反応ノート

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