Ethyl bromoacetate → Ethyl[3-(5-methoxy-2-phenylindol-1-ylmethyl)phenoxy]acetate

HRID 1191679Notes

Reaction equation

HRID 1191679 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C)C=O.O>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][O:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:4]([CH2:5][N:6]2[C:14]3[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=3)[CH:8]=[C:7]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]=1)[CH3:38]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 696709171-(3-Hydroxybenzyl)-5-methoxy-2-phenylindole

Product 1

HCID 67684511Ethyl[3-(5-methoxy-2-phenylindol-1-ylmethyl)phenoxy]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-hydroxybenzyl)-5-methoxy-2-phenylindole (108 mg) in N,N-dimethylformamide (1.3 mL) was added potassium carbonate (68.2 mg) at room temperature. Then ethyl bromoacetate (0.047 mL) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (129 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-82bc56f77c5346778df20699f381fdb7
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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