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

HRID 387830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387830
[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.[F:20][CH2:21][CH2:22][NH:23][C:24](=O)[O:25]C1C=CC=CC=1.O>CN(C)C=O>[F:20][CH2:21][CH2:22][NH:23][C:24]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][C:8]3[CH:7]=[CH:6][N:5]=[C:4]([NH2:3])[CH:9]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)=[O:25]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 219493654-(1H-5-indolyloxy)-2-pyridinamineHCID 22936733Phenyl (2-fluoroethyl)carbamate

Produkt 1

HCID 58931263N1-(2-Fluoroethyl)-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamideAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil) (360 mg) was added to a solution of 2.0 g of 5-[(2-amino-4-pyridyl)oxy]-1H-indole in 30 ml of dimethylformamide at room temperature. After stirring for 5 minutes, the mixture was placed in an ice bath and 1.8 g of phenyl N-(2-fluoroethyl)carbamate was added while cooling. The mixture was returned to room temperature and stirred for 30 minutes, after which water was added and extraction was performed with ethyl acetate. The extract was passed through a glass filter coated with silica gel. The ethyl acetate layer was washed once with bicarbonate water and dried over magnesium sulfate. The drying agent was filtered off to obtain 1.93 g of a faint brown powder.

Aufarbeitung

  1. customthe mixture was placed in an ice bath
  2. temperaturewhile cooling
  3. customwas returned to room temperature
  4. stirringstirred for 30 minutes
  5. extractionextraction
  6. filtrationfilter
  7. washThe ethyl acetate layer was washed once with bicarbonate water
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe drying agent was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-7a3e94728f08414ebf5d15a3f9d79058
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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