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Water → N1-Phenyl-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamide

HRID 1433461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433461
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:7]=[CH:6][N:5]=1.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[C:20]1([NH:26][C:27]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([O:10][C:8]4[CH:7]=[CH:6][N:5]=[C:4]([NH2:3])[CH:9]=4)=[CH:19][CH:18]=3)[CH:14]=[CH:15]2)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 219493654-(1H-5-indolyloxy)-2-pyridinamine

Produkt 1

HCID 21949159N1-Phenyl-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamideAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

After adding 28 mg of sodium hydride (60% in oil) to a solution of 3.0 g of 5-[(2-amino-4-pyridyl)oxy]-1H-indole in dimethylformamide at room temperature and stirring the mixture for 5 minutes, 1.6 g of phenyl isocyanate was added and the mixture was stirred for 20 minutes. Water was added, extraction was performed with ethyl acetate and the organic layer was washed with water, and then silica gel was added and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel and purified by column chromatography (ethyl acetate), to obtain 3.4 g of a colorless powder.

Aufarbeitung

  1. stirringthe mixture was stirred for 20 minutes
  2. extractionextraction
  3. washthe organic layer was washed with water
  4. additionsilica gel was added
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionThe silica gel was charged into a dry column
  7. custompurified by column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-aa8687d4b5874219a01fa0d3b2145267
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612092B2

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