Allyl bromide → Ethyl 3-(1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-allyloxyindol-2-yl)-2,2dimethylpropionate

HRID 37444Notes

Reaction equation

HRID 37444 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[Cl:5][C:6]1[CH:36]=[CH:35][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[C:13]([S:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[C:12]2[CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:8][CH:7]=1>CN(C=O)C.[Cl-].[Na+].O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:3][CH:2]=[CH2:1])=[CH:17][CH:18]=3)[C:13]([S:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[C:12]2[CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 19935664Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 19935665Ethyl 3-(1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-allyloxyindol-2-yl)-2,2dimethylpropionateYield 86.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of allyl bromide (1.81 g, 15 mmol) potassium carbonate (4.14 g, 30 mmol) and ethyl 3-(1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl)-2,2dimethylpropionate (7.15 g, 15 mmol), prepared as in step 3, in anhydrous DMF (40 ml) was heated at 60° C for 3 hours, and stirred at ambient temperature for 17 hours. The reaction mixture was diluted with brine and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a white solid. The solid was triturated with hexane (100 ml), filtered and dried in vacuo dried to obtain 6.65g of ethyl 3-(1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-allyloxyindol-2-yl)-2,2dimethylpropionate as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a white solid
  7. customThe solid was triturated with hexane (100 ml)
  8. filtrationfiltered
  9. customdried in vacuo
  10. customdried

Sources & evidence

ORD record
ord-02939f7a21d44857b94b6c857f5e3722
Source dataset
uspto-grants-1995_05
Patent number
US05420282

Reaction notes

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