Indole-3-Carboxaldehyde → HCID 19091983, compound

HRID 1361001Notes

Reaction equation

HRID 1361001 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=[O:2].Br[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([CH:1]=[O:2])=[CH:4]1)[CH3:19]

Participants

5

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 19091983HCID 19091983, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-formylindol (10 g, 69 mmol), ethyl 3-bromopropionate (10.5 mL, 83 mmol) and potassium carbonate (28.5 g, 207 mmol) and acetonitrile (100 mL) was stirred vigorously at refux temperature for 2 days. After cooling, the mixture was filtered and the filtrate was concentrated in vacuo to afford 17.5 g (quant.) of 3-(3-formylindol-1-yl)propionic acid ethyl ester as a solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2f110b35e0ed42ee9a98f4614d0490a8
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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