Isobutyl iodide → (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isobutyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898240ノート

反応式

HRID 898240 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-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH:39]([CH3:41])[CH3:40]>C(#N)C>[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)[N:5]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:4]1=[O:24])[CH3:2]

参加物

6

反応物 4

HCID 10556Isobutyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69223657(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

生成物 1

HCID 69223598(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isobutyl-3,4-dihydroquinoxalin-2(1H)-one収率 35%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
74 °C

実験手順

To a stirred solution of (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 8) (0.25 g, 0.76 mmol) in acetonitrile (6 mL) under nitrogen was added cesium carbonate (0.13 g, 0.40 mmol), potassium carbonate (0.055 g, 0.40 mmol) and 1-iodo-2-methylpropane (0.30 mL, 0.48 g, 2.6 mmol). The mixture was stirred at 74° C. for 12 h. The solvent was then evaporated, and the residue was partitioned between methylene chloride and water. The organic layer was separated, washed with water, 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 0.10 g (35%) of (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isobutyl-3,4-dihydroquinoxalin-2(1H)-one.

後処理

  1. customThe solvent was then evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried 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)

出典と根拠

ORDレコード
ord-2483fd9fc51e49288c66c4fbe821b533
出典データセット
uspto-grants-2008_04
特許番号
US07351709B2

反応ノート

読み込み中…