Ethyl bromoacetate → HCID 16090860, compound

HRID 68323Notes

Reaction equation

HRID 68323 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 160545-Hydroxyindole

Product 1

HCID 16090860HCID 16090860, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy indole (4.56 gm, 0.034 moles) in DMF (20 ml), potassium carbonate (9.43 gm, 0.068 moles), ethyl bromoacetate (6.29 gm, 0.0377 moles) were added and the reaction mixture was stirred at ambient temperature for 12 hours. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure to yield 6.2 gm (82%) of product as solid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water & brine
  5. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-c3a00c6c3b4e4c9da149357566147e0b
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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