2-[1-(3-hydroxypropyl)-1H-indol-3-yl]acetamide → 3-(1-Methyl-1H-indol-4-yl)-4-[1-(3-hydroxypropyl)-1H-indol-3-yl]pyrrole-2,5-dione

HRID 751534Notes

Reaction equation

HRID 751534 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C:21]([NH2:23])=[O:22])=[CH:12]1.C[O:25][C:26](=O)[C:27]([C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[CH:31]=[CH:32][N:33]2[CH3:38])=O>CN(C)C=O>[CH3:38][N:33]1[C:34]2[C:30](=[C:29]([C:27]3[C:26](=[O:25])[NH:23][C:21](=[O:22])[C:20]=3[C:13]3[C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:11]([CH2:10][CH2:9][CH2:8][OH:7])[CH:12]=3)[CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:32]1

Participants

5

Reactant 3

HCID 106572082-[1-(3-hydroxypropyl)-1H-indol-3-yl]acetamideHCID 23665647Potassium tert-butoxideHCID 69269926(1-methyl-1H-indol-4-yl)oxoacetic acid methyl ester

Product 1

HCID 102875073-(1-Methyl-1H-indol-4-yl)-4-[1-(3-hydroxypropyl)-1H-indol-3-yl]pyrrole-2,5-dioneYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add potassium tert-butoxide (4.1 ml, 4.1 mmol, 1M in tetrahydrofuran) to a suspension of 2-[1-(3-hydroxypropyl)-1H-indol-3-yl]acetamide (0.32 g, 1.38 mmol) and (1-methyl-1H-indol-4-yl)oxoacetic acid methyl ester (0.30 g, 1.38 mmol) in dimethylformamide (10 ml). Stir the reaction at room temperature for 12 hours, quench with 1N HCl, and extract into ethyl acetate. Wash the organic extract with 5% aqueous lithium chloride and saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from neat hexanes to 100% ethyl acetate:hexane to obtain the title compound (0.3 g, 54%) as a red solid. ES(M++1)400.2 ES(M−−1)398.6.

Workup

  1. customthe reaction at room temperature for 12 hours
  2. customquench with 1N HCl
  3. extractionextract into ethyl acetate
  4. washWash the
  5. extractionorganic extract with 5% aqueous lithium chloride and saturated aqueous sodium chloride
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-6c788497e8ac4a1f8a273b55df579c2f
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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