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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
ノート
印刷プレビュー

反応式

HRID 751534 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6c788497e8ac4a1f8a273b55df579c2f
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07405305B2

反応ノート

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