Sodium hydride → tert-Butyl (5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)acetate

HRID 521186ノート

反応式

HRID 521186 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.[H-].[Na+].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:5]2

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 86729353tert-Butyl (5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

5-Bromo-2,3-dihydro-1H-isoindol-1-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0° C. NaH (38 mg, 0.94 mmol, 60% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0° C. for 15 minutes before tert-butyl bromoacetate (92 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0° C. for 30 minutes before saturated aqueous NaHCO3 (10 mL) was carefully added. The mixture was extracted with EtOAc, and the organic layer was washed with water, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-20% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound. LRMS (ESI) calc'd for C14H16BrNO3 [M+Na]+: 348. Found: 348.

後処理

  1. additionwas added
  2. additionwas carefully added
  3. extractionThe mixture was extracted with EtOAc
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by MPLC on silica gel (
  9. washa gradient elution of 0-20% EtOAc/hexanes)
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a549963f323f4d8186a298dc7a01065f
出典データセット
uspto-grants-2016_05
特許番号
US09328099B2

反応ノート

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