Iodoethane → HCID 21071402, compound

HRID 1666851Notes

Reaction equation

HRID 1666851 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:31][CH3:32].CCOC(C)=O>CN1CCCC1=O.[Cl-].[Na+].O>[CH2:31]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[C:14](=[O:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]1=[O:22])[CH3:32]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 7901972-(2-(5-hydroxy-1H-indol-3-yl)ethyl)isoindole-1,3-dione

Product 1

HCID 21071402HCID 21071402, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Combine 2-(2-(5-hydroxy-1H-indol-3-yl)ethyl)isoindole-1,3-dione (900 mg, 2.9 mmol), cesium carbonate (960 mg, 2.9 mmol) and 1-iodoethane (920 mg, 5.9 mmol) in N-methylpyrrolidinone (5 mL) and stir at ambient temperature for 4 hours, pour into brine and extract twice with EtOAc. Wash the combined extracts three times with brine, dry over MgSO4, and concentrate under vacuum to give an oil. Chromatograph the oil on silica gel eluting with 20% EtOAc in hexanes to give the title compound as a white solid: ISMS 335 (M+1); Analysis for C20H18N2O3: calcd: C, 71.84; H, 5.43; N, 8.38. found: C, 71.97; H, 5.47; N, 8.36.

Workup

  1. extractionextract twice with EtOAc
  2. washWash the combined extracts three times with brine
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate under vacuum
  5. customto give an oil

Sources & evidence

ORD record
ord-9babe148bd2b484f9caeef5947b00bb9
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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