p-Toluenesulfonic acid → 1H-Pyrrole-2,5-dione, 3,4-bis(1-methyl-1H-indol-3-yl)-

HRID 1609393ノート

反応式

HRID 1609393 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=O)[C:12]([OH:14])=O)=[CH:3]1.C(N(CC)CC)C.ClC(OCC(C)C)=O.Cl.[CH3:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]([CH2:42][C:43](=[NH:48])[O:44]C(C)C)=[CH:34]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH3:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]([C:42]2[C:43](=[O:44])[NH:48][C:12](=[O:14])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:34]1

参加物

7

反応物 5

HCID 6101p-Toluenesulfonic acidHCID 8471Triethylamine2 回HCID 62365Isobutyl chloroformateHCID 4589028N-Methyl-3-indoleglyoxylic acidHCID 22907276Isopropyl 1-methyl-3-indoleacetimidate hydrochloride

生成物 1

HCID 53276551H-Pyrrole-2,5-dione, 3,4-bis(1-methyl-1H-indol-3-yl)-収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A stirred solution of 406 mg (2 mmol) of 1-methyl-3-indolylglyoxylic acid in 20ml of dichloromethane was treated with 202 mg (2 mmol) of triethylamine and 273 mg (2 mmol) of isobutyl chloroformate. After 0.5 hour, the solution was added dropwise to a stirred solution of 533 mg (2 mmol) of isopropyl 1-methyl-3-indoleacetimidate hydrochloride and 808 mg (8 mmol) of triethylamine in 50 ml of dichloromethane. The solution obtained was heated to reflux under nitrogen for 18 hours, cooled and treated with 1.9 g (10 mmol) of p-toluenesulfonic acid. After 1 hour, the solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel using dichloromethane/ethyl acetate (8:1) for the elution to give 107 mg(30% ) of 3,4-bis-(1 -methyl-3-indolyl)-1H-pyrrole-2,5-dione in the form of an orange colored solid of melting point >310° C.

後処理

  1. customThe solution obtained
  2. temperaturewas heated
  3. temperatureto reflux under nitrogen for 18 hours
  4. temperaturecooled
  5. waitAfter 1 hour
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography on silica gel
  8. washfor the elution

出典と根拠

ORDレコード
ord-596341b7a3734edf99bc8fea3d8c8aed
出典データセット
uspto-grants-1995_03
特許番号
US05399712

反応ノート

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