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

HRID 1947054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947054
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:4]1.[CH2:16]([S:20][C:21]1[N:26]=[C:25](Cl)[CH:24]=[CH:23][N:22]=1)[CH2:17][CH2:18][CH3:19]>CN(C=O)C>[CH2:16]([S:20][C:21]1[N:22]=[C:23]([N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:4]2)[CH:24]=[CH:25][N:26]=1)[CH2:17][CH2:18][CH3:19]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 189604091H-indole-3-sulfonamideHCID 597434972-Butylsulfanyl-4-chloro-pyrimidine

Produkt 1

HCID 693097221-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indole-3-sulfonic acid amideAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (147 mg, 3.67 mmol, 60% dispersion) was added to a solution of 1H-indole-3-sulfonic acid amide (600 mg, 3.06 mmol) in DMF (5 mL) at 0° C., and stirred for 15 min. 2-Butylsulfanyl-4-chloro-pyrimidine (682 mg, 3.36 mmol) was added, and washed down with additional DMF (2 mL). The reaction mixture was allowed to warm to RT, and stirred overnight under N2. The reaction mixture was then poured into water, extracted with hot EtOAc, washed with water, brine, and filtered. The mixture was concentrated to half volume, heated on a steam bath, and allowed to crystallize. The resulting white solid was filtered off, washed with DCM, and air-dried to provide 1-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indole-3-sulfonic acid amide (868 mg, 71.4% yield).

Aufarbeitung

  1. washwashed down with additional DMF (2 mL)
  2. stirringstirred overnight under N2
  3. additionThe reaction mixture was then poured into water
  4. extractionextracted with hot EtOAc
  5. washwashed with water, brine
  6. filtrationfiltered
  7. concentrationThe mixture was concentrated to half volume
  8. temperatureheated on a steam bath
  9. customto crystallize
  10. filtrationThe resulting white solid was filtered off
  11. washwashed with DCM
  12. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-6bd8bca294334ef296c80009c4815567
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399462B2

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