Potassium Iodide → HCID 2194468, compound

HRID 337607Notes

Reaction equation

HRID 337607 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[I-].[K+].Br[CH2:17][CH2:18][O:19][CH3:20]>CN(C=O)C>[CH3:20][O:19][CH2:18][CH2:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl ether

Product 1

HCID 2194468HCID 2194468, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Indole-3-carbaldehyde (1 eq.) was dissolved in DMF (0.46 M). Sodium hydride was added (1.3 eq.) and the resulting solution was stirred at RT for 20 min. Potassium iodide (1 eq.) and 1-bromo-2-methoxyethane (2 eq.) were then added and the reaction solution was allowed to stir at RT for 48 h. The reaction mixture was subsequently quenched with brine and extracted with EtOAc. The combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as an orange oil.

Workup

  1. stirringto stir at RT for 48 h
  2. customThe reaction mixture was subsequently quenched with brine
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationFiltration and concentration of the filtrate in vacuo
  6. customafforded a yellow oil
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-84a19ace8be6489f92512fca38a3d35c
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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