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

HRID 129845Notes

Reaction equation

HRID 129845 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-62312a2be2cc43c68a121d308933f694
Source dataset
uspto-grants-1995_11
Patent number
US05470870

Reaction notes

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