1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9947705, compound

HRID 642167Notes

Reaction equation

HRID 642167 reaction equation
[I: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].C1CCN2C(=NCCC2)CC1.Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:6](=[O:11])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 886955-IodoisatinHCID 107604Methyl 4-bromobutyrate

Product 1

HCID 9947705HCID 9947705, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 5-iodo-1H-indole-2,3-dione (1.0 g, 3.66 mmol) in anhydrous THF (18 ml) were added DBU (0.82 mL, 5.49 mmol) and methyl 4-bromobutanoate (0.6 mL, 5.49 mmol). After stirring at rt for 2 hrs, the reaction mixture was quenched with water (60 mL) and HCl (IN, 10 mL). Extraction with EtOAc (3×50 mL), drying over MgSO4 and evaporation under vacuo gave a residue. Purification by flash chromatography (chexanes/Et2O (1/3)) gave the title compound as an orange powder (1.10 g, 71%) in 90.1% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customthe reaction mixture was quenched with water (60 mL) and HCl (IN, 10 mL)
  2. extractionExtraction with EtOAc (3×50 mL)
  3. dry with materialdrying over MgSO4 and evaporation under vacuo
  4. customgave a residue
  5. customPurification by flash chromatography (chexanes/Et2O (1/3))

Sources & evidence

ORD record
ord-ddcb0b45d65e48a7bd6ffc2599e2d63f
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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