Ammonium Hydroxide → 3-(1-methylindol-3-yl)4-[3-(2-morpholin-4-ylethyloxy)phenyl]-1H-pyrrole-2,5-dione

HRID 1017564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017564
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[O:13][C:14](=O)[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:17]=2)=[CH:3]1.[OH-].[NH4+:34]>CN(C=O)C.O.CO.C(Cl)Cl>[NH4+:2].[OH-:13].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[NH:34][C:14](=[O:13])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:17]=2)=[CH:3]1

Komponenten

8

Edukt 2

HCID 14923Ammonium HydroxideHCID 120181343-(1-Methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]furan-2,5-dione

Produkt 2

HCID 14923Ammonium HydroxideAusbeute 10 %HCID 120181353-(1-methylindol-3-yl)4-[3-(2-morpholin-4-ylethyloxy)phenyl]-1H-pyrrole-2,5-dioneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

3-(1-Methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]furan-2,5-dione was then dissolved in DMF (5 mL) and ammonium hydroxide (10 mL) was added. The resulting mixture was heated at 140° C. for 4 h, then cooled to room temperature, and diluted with water. The product was extracted into EtOAc. The EtOAc layer was washed with NaCl (sat.) and dried over sodium sulfate. Purificaiton on a silica gel column with 5% (10% NH4OH in MeOH) in CH2Cl2 gave 3-(1-methylindol-3-yl)4-[3-(2-morpholin-4-ylethyloxy)phenyl]-1H-pyrrole-2,5-dione (0.21 g, >99% yield).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionThe product was extracted into EtOAc
  3. washThe EtOAc layer was washed with NaCl (sat.)
  4. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-dfe650e420f54202a398323a2b199f5d
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479490B2

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