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

HRID 1078425Notes

Reaction equation

HRID 1078425 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 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 in vacuo
  5. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-f1eb71ad1c784e6f88143e9074caa719
Source dataset
uspto-grants-1996_08
Patent number
US05547991

Reaction notes

Loading…