4-Hydroxy-2-Butanone → 3-(1-methylindol-3-yl)-4-[3-(3-hydroxy-1-methylpropylamino)phenyl]-1H-pyrrole-2,5-dione

HRID 1017581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017581
[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:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)=[CH:3]1.[OH:25][CH2:26][CH2:27][C:28](=O)[CH3:29].[BH3-]C#N.[Na+]>ClCCl>[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:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH:28]([CH3:29])[CH2:27][CH2:26][OH:25])[CH:17]=2)=[CH:3]1

Komponenten

5

Edukt 3

HCID 1115094-Hydroxy-2-ButanoneHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

Produkt 1

HCID 120181463-(1-methylindol-3-yl)-4-[3-(3-hydroxy-1-methylpropylamino)phenyl]-1H-pyrrole-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (0.2 g, 0.6 mmol) and 4-hydroxy-2-butanone (80 mg, 1.5 eq) in dichloromethane (15 mL) was added NaCNBH3 (56 mg, 1.5 eq) and the reaction mixture was stirred at RT for three days. The product 3-(1-methylindol-3-yl)-4-[3-(3-hydroxy-1-methylpropylamino)phenyl]-1H-pyrrole-2,5-dione separated by preparatory TLC (8.9 mg, 3.6%). LC/mS: M+ 389.

Aufarbeitung

  1. customThe product 3-(1-methylindol-3-yl)-4-[3-(3-hydroxy-1-methylpropylamino)phenyl]-1H-pyrrole-2,5-dione separated by preparatory TLC (8.9 mg, 3.6%)

Quellen und Nachweise

ORD-Eintrag
ord-f056e563042d437cac3344b221da3d6e
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479490B2

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