Tetrahydrofuran → HCID 67427784, compound

HRID 1662738Notes

Reaction equation

HRID 1662738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[H-].[Na+].[NH4+:15].[Cl-].C[CH2:18][O:19][C:20]([CH3:22])=O.[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([OH:12])[C:27]1[CH:23]=[C:24]([C:2]2[CH:3]=[CH:4][N:15]=[CH:9][CH:10]=2)[CH:25]=[CH:22][C:20]=1[O:19][CH3:18]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 67427784HCID 67427784, compound

Procedure

Under nitrogen atmosphere to a suspension of 1.33 g of 5-chloroisatin in THF (31.5 ml) was added 555 mg of NaH under ice cooling and the reaction mixture was stirred for one hour under the same conditions. To the reaction solution was added dropwise the lithiation reagent prepared above over 5 minutes and the reaction solution was stirred for one hour under ice cooling. An aqueous solution of saturated NH4Cl and EtOAc were added to the reaction solution; liquid separation was performed and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with saturated brine, dried over MgSO4, then, the drying agent was separated by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: CHCl3/MeOH/NH4OH=97/3/0.3 to 90/10/0.9; v/v/v) to obtain 1.85 g of the title compound (pale brown solid).

Workup

  1. additionTo the reaction solution was added dropwise the lithiation reagent
  2. customprepared above over 5 minutes
  3. stirringthe reaction solution was stirred for one hour under ice cooling
  4. customliquid separation
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over MgSO4
  8. customthe drying agent was separated by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: CHCl3/MeOH/NH4OH=97/3/0.3 to 90/10/0.9; v/v/v)

Sources & evidence

ORD record
ord-dc6e2cfec1224784810736d05d7c85e8
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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