Potassium Carbonate → Ethyl 2-(hydroxyimino)-3-(4,6-dibromo-3-indolyl)propanoate

HRID 375217Notes

Reaction equation

HRID 375217 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20](=[N:26][OH:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl.C(OCC)(=O)C>[OH:27][N:26]=[C:20]([CH2:19][C:4]1[C:3]2[C:7](=[CH:8][C:9]([Br:11])=[CH:10][C:2]=2[Br:1])[NH:6][CH:5]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 140260574,6-Dibromo-1H-indoleHCID 53428735Ethyl 3-bromo-2-(hydroxyimino)propanoate

Product 1

HCID 73607731Ethyl 2-(hydroxyimino)-3-(4,6-dibromo-3-indolyl)propanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Mix 4,6-dibromoindole (2.09 g, 7.58 mmol), potassium carbonate (1.57 g, 11.4 mmol) and anhydrous methylene chloride (30 mL). Stir and add a solution of ethyl 3-bromo-2-hydroxyiminopropanoate (1.59 g, 7.58 mmol) in methylene chloride (20 mL). Stir under a nitrogen atmosphere for 48 hours. Take the solution up in ethyl acetate and wash with water (100 mL ), saturated sodium hydrogen carbonate (100 mL ) and brine (100 mL). Dry (MgSO4) and evaporate the solvent in vacuo and purify by silica gel chromatography to give the title compound.

Workup

  1. stirringStir under a nitrogen atmosphere for 48 hours
  2. washwash with water (100 mL ), saturated sodium hydrogen carbonate (100 mL ) and brine (100 mL)
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-c4fc81ffcbd2482fbd5049776ba66661
Source dataset
uspto-grants-1996_01
Patent number
US05484814

Reaction notes

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