Allyl bromide → Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

HRID 434016Notes

Reaction equation

HRID 434016 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:24][CH:23]=[CH2:22])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 13286893Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylateYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-hydroxyindole-2-carboxylic acid ethyl ester (14.2 g, 68.5 mmol) in DMF (150 mL) was added cesium carbonate (26.8 g, 82.3 mmol). The resulting mixture was stirred at room temperature for 20 min followed by the addition of allyl bromide (5.94 mL, 68.5 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction was diluted with ethyl acetate, washed with H2O, brine and dried (Na2SO4). The solvent was removed in vacua and the resulting crude product was purified by flash column chromatography on silica gel (0-20% EtOAc/hexanes) to give the desired material as solid (8.9 g, 52%). LC/MS (ES+) m/e 248 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 24 h
  2. washwashed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed in vacua
  5. customthe resulting crude product was purified by flash column chromatography on silica gel (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-017d9775f4214212acb518c5f2f1d411
Source dataset
uspto-grants-2003_12
Patent number
US06670388B1

Reaction notes

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