Sodium hydride → 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-methoxy-1H-indole-3-carboxylic acid amide

HRID 1947061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947061
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([C:14]([NH2:16])=[O:15])=[CH:8][NH:9]2.[CH2:17]([S:21][C:22]1[N:27]=[C:26](Cl)[CH:25]=[CH:24][N:23]=1)[CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:17]([S:21][C:22]1[N:23]=[C:24]([N:9]2[C:10]3[C:6](=[C:5]([O:4][CH3:3])[CH:13]=[CH:12][CH:11]=3)[C:7]([C:14]([NH2:16])=[O:15])=[CH:8]2)[CH:25]=[CH:26][N:27]=1)[CH2:18][CH2:19][CH3:20]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 597434972-Butylsulfanyl-4-chloro-pyrimidineHCID 693120594-methoxy-1H-indole-3-carboxylic acid amide

Produkt 1

HCID 693120521-(2-butylsulfanyl-pyrimidin-4-yl)-4-methoxy-1H-indole-3-carboxylic acid amideAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

NaH (397 mg, 9.94 mmol, 60% dispersion) was added to a solution of 4-methoxy-1H-indole-3-carboxylic acid amide (1.575 g, 8.28 mmol) in dry DMF (5 mL) at 0° C., stirred for 20 min, and a solution of 2-butylsulfanyl-4-chloro-pyrimidine (1.846 g, 9.108 mmol) in DMF (4 mL) added at 0° C. The mixture was allowed to warm up to RT without stirring, whereupon a solid precipitated. Dry THF (20 mL) was added, and the mixture stirred overnight. Water was added to the mixture, and the resulting white solid was filtered off, washed with water (20 mL) and DCM (20 mL), and air-dried for 3 h to provide 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-methoxy-1H-indole-3-carboxylic acid amide (2.916 g, 98.8% yield) as a crude solid.

Aufarbeitung

  1. stirringwithout stirring, whereupon a solid
  2. customprecipitated
  3. additionDry THF (20 mL) was added
  4. stirringthe mixture stirred overnight
  5. additionWater was added to the mixture
  6. filtrationthe resulting white solid was filtered off
  7. washwashed with water (20 mL) and DCM (20 mL)
  8. customair-dried for 3 h

Quellen und Nachweise

ORD-Eintrag
ord-cb27d6c27cf24460823bab34cc9bc0f2
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399462B2

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