Sodium Iodide → 1-[2-(tert-Butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one

HRID 558988ノート

反応式

HRID 558988 の反応式
[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[NH:6][CH2:7][C:8](=[O:14])[NH:9]2.Br[CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].[I-].[Na+]>[Cl-].[Na+].O>[Si:19]([O:18][CH2:17][CH2:16][N:9]1[C:10]2[C:5](=[C:4]([F:3])[CH:13]=[CH:12][CH:11]=2)[NH:6][CH2:7][C:8]1=[O:14])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 229128785-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

生成物 1

HCID 670000521-[2-(tert-Butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

Sodium hydride (60%, 128 mg, 3.2 mmol) was added to a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (530 mg, 3.2 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 10 min. (2-Bromoethoxy)-tert-butyldimethylsilane (789 mg, 3.3 mmol) and sodium iodide (495 mg, 3.3 mmol) were added and the mixture was stirred for 18 h. Brine was added and the mixture was evaporated in vacuo. The residue was taken up in EtOAc and brine, separated and the organic layer was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet.ether 40:60) to give a pale yellow solid: yield 600 mg, 58%.

後処理

  1. temperaturewhile cooling in an ice/water bath
  2. additionwere added
  3. customthe mixture was evaporated in vacuo
  4. custombrine, separated
  5. customthe organic layer was dried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet.ether 40:60)
  8. customto give a pale yellow solid

出典と根拠

ORDレコード
ord-e129901dc95c43a0a99044a4205ebf58
出典データセット
uspto-grants-2011_11
特許番号
US08063038B2

反応ノート

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