Water → HCID 54285481, compound

HRID 654469Notes

Reaction equation

HRID 654469 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].O>CN(C=O)C>[CH2:3]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 2311683-Benzyl-1H-indole

Product 1

HCID 54285481HCID 54285481, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (50% dispersion in oil, 170 mg, 3.5 mmol) in DMF (15 mL), at r.t. and under an atmosphere of nitrogen, there was added in portions 3-benzylindole (ref: Tetrahedron 23, 3771-83 (1967)) (621 mg, 3 mmol) and the mixture was stirred for 1 hour. There added methyl bromoacetate (765 mg, 5 mmol) and stirring was continued for 1.5 hours. H2O (100 mL) was added and the mixture was extracted twice with Et2O. These extracts were H2O with water, dried over MgSO4 and evaporated to a residue which was chromatographed on silica gel eluting with a 1:5 mixture of EtOAc acetate and hexane to afford the title product as an oil.

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 hours
  3. extractionthe mixture was extracted twice with Et2O
  4. dry with materialdried over MgSO4
  5. customevaporated to a residue which
  6. customwas chromatographed on silica gel eluting with a 1:5 mixture of EtOAc acetate and hexane

Sources & evidence

ORD record
ord-1937b03e8264402bb0838a416efbe3f5
Source dataset
uspto-grants-1992_07
Patent number
US05132319

Reaction notes

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