Tetrahydro-4H-pyran-4-one → 3-(1-methylindol-3-yl)-4-(3-tetrahydropyran-4-ylaminophenyl)-1H-pyrrole-2,5-dione

HRID 1017576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017576
[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.[O:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1.[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][CH:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)[CH:17]=2)=[CH:3]1

Komponenten

5

Edukt 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

Produkt 1

HCID 120181393-(1-methylindol-3-yl)-4-(3-tetrahydropyran-4-ylaminophenyl)-1H-pyrrole-2,5-dioneAusbeute 70 %

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 tetrahydro-4H-pyran-4-one (65 mg, 0.65 mmol) in MeOH (8 mL) was stirred at room temperature for 40 min., and then NaCNBH3 (63 mg, 1.0 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 give 3-(1-methylindol-3-yl)-4-(3-tetrahydropyran-4-ylaminophenyl)-1H-pyrrole-2,5-dione (88.2 mg, 70%). LC/MS: M+ 401(98.6%).

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-8fa03dfec6434a34aedf7cc9e3667cee
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479490B2

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