4-Methoxybenzenesulfonyl chloride → 3-[5-Methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

HRID 2100434Notes

Reaction equation

HRID 2100434 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1.[H-].[Na+].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([S:28]([C:25]2[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=2)(=[O:30])=[O:29])[CH:7]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 54357260Methyl 3-(5-methoxy-1H-indol-3-yl)propanoate

Product 1

HCID 588431163-[5-Methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-propionic acid methyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution (0° C.) of indole-3-propionic acid methyl ester 4 (0.797 g, 3.42 mmol) in DMF (20 mL) was added sodium hydride (60%; 0.25 g; 0.0625 mol) was added in one portion and stirred for 30 min followed by the addition of 4-methoxybenzenesulfonyl chloride (1.3 g; 6.31 mmol). The reaction was allowed to warm up to room temperature and stirred for 16 h, subjected to aqueous work up, and product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, evaporated under reduced pressure, and purified by flash-chromatography (silica gel; 80% n-hexane-20% ethyl acetate) to afford the ester 5 as a white solid (0.83 g; 61% yield; M+1=404.1).

Workup

  1. additionwas added in one portion
  2. stirringstirred for 16 h
  3. extractionproduct was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. custompurified by flash-chromatography (silica gel; 80% n-hexane-20% ethyl acetate)

Sources & evidence

ORD record
ord-a5e59a3c5d6545d8a700a6083c4bded0
Source dataset
uspto-grants-2009_08
Patent number
US07572806B2

Reaction notes

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