Allyl bromide → 1-Allyl-1H-indole-3-carbaldehyde

HRID 337610Notes

Reaction equation

HRID 337610 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+].[CH2:14](Br)[CH:15]=[CH2:16]>CN(C=O)C>[CH2:16]([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)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 8015161-Allyl-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Indole-3-carbaldehyde (1 eq.) was dissolved in DMF (0.46 M). Sodium hydride was added (2.5 eq.) and the resulting solution was stirred at RT for 20 min. Allyl bromide (1 eq.) was then added and the reaction solution was allowed to stir at RT for 20 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, 4:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a light yellow oil.

Workup

  1. stirringto stir at RT for 20 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, 4:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-07bd0308512d4a52833cc5bbb00b9d0e
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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