1H-imidazole-2-carbaldehyde → 3-(1-methylindol-3-yl)-4-[3-(imidazol-2-ylmethylamino) phenyl]-1H-pyrrole-2,5-dione

HRID 1017578

Reaktionsgleichung

Reaktionsgleichung von HRID 1017578
[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.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.[BH3-]C#N.[Na+]>CO>[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][CH2:30][C:26]3[NH:25][CH:29]=[CH:28][N:27]=3)[CH:17]=2)=[CH:3]1

Komponenten

5

Edukt 3

HCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

Produkt 1

HCID 120181403-(1-methylindol-3-yl)-4-[3-(imidazol-2-ylmethylamino) phenyl]-1H-pyrrole-2,5-dioneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.32 mmol) and imidazole-2-carboxaldehyde (40 mg, 0.42 mmol) in MeOH (8 mL) was stirred for 15 min., and then NaCNBH3 (40.2 mg, 0.64 mmol) was added. After stirring the reaction mixture overnight the volatiles were removed under vacuo and the residue was purified by preparatory TLC (3% MeOH/CH2Cl2) to afford 3-(1-methylindol-3-yl)-4-[3-(imidazol-2-ylmethylamino)phenyl]-1H-pyrrole-2,5-dione (24.8 mg, 20 %). LC/MS: M+ 397(94.2%).

Aufarbeitung

  1. stirringAfter stirring the reaction mixture overnight the volatiles
  2. customwere removed under vacuo
  3. customthe residue was purified by preparatory TLC (3% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-ed999bf1bf4f414aad2ebc259f7562a5
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479490B2

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