3-((Tert-butyldimethylsilyl)oxy)propanal → 3-(1-Methylindol-3-yl)-4-[3-(3-tert-butyldimethylsilyloxypropylamino)phenyl]-1h-pyrrole-2,5-dione

HRID 1017580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017580
[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.[Si:25]([O:32][CH2:33][CH2:34][CH:35]=O)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[BH3-]C#N.[Na+]>C(Cl)Cl.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][CH2:35][CH2:34][CH2:33][O:32][Si:25]([C:28]([CH3:29])([CH3:31])[CH3:30])([CH3:26])[CH3:27])[CH:17]=2)=[CH:3]1

Komponenten

6

Edukt 3

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanalHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

Produkt 1

HCID 120181423-(1-Methylindol-3-yl)-4-[3-(3-tert-butyldimethylsilyloxypropylamino)phenyl]-1h-pyrrole-2,5-dioneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (0.2 g, 6 mmol) and 3-(tert-butyldimethylsilyloxy)propionaldehyde (0.25 g, 13 mmol) in CH2Cl2 (10 mL) and MeOH (5 mL) was stirred at room temperature for 15 min and then NaCNBH3 (57 mg, 1.5 eq) was added. The reaction mixture was stirred at RT overnight and then concentrated under vacuo. The residue was purified by preparatory TLC to give 98 mg 3-(1-methylindol-3-yl)-4-[3-(3-tert-butyldimethylsilyloxypropylamino)phenyl]-1H-pyrrole-2,5-dione (32%) MS (LSIMS): (M+H)+ 490, MP: 58-65° C.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at RT overnight
  2. concentrationconcentrated under vacuo
  3. customThe residue was purified by preparatory TLC

Quellen und Nachweise

ORD-Eintrag
ord-4b89cb28b6fd4721a742e1979307e493
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479490B2

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