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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 751534
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HRID 751534 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c788497e8ac4a1f8a273b55df579c2f
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07405305B2

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