Triethylamine → 5-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

HRID 1806218

Reaktionsgleichung

Reaktionsgleichung von HRID 1806218
C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[CH3:28][CH:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30]>CN(C=O)C.CCOC(C)=O.O>[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:22]1[CH2:27][CH2:26][N:25]([S:31]([CH:29]([CH3:30])[CH3:28])(=[O:33])=[O:32])[CH2:24][CH2:23]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 667232845-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride

Produkt 1

HCID 577326275-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Versuchsvorschrift

Triethylamine (2.6 mL, 18.7 mmol) was added to a solution of 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride in DMF (15 mL) at 0° C. The mixture was stirred at room temperature for 10 min, and 2-propanesulfonyl chloride (1.04 mL, 9.32 mmol) was added. Stirring continued for another 30 min, and the reaction mixture was diluted with 1:1 EtOAc/H2O (200 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with saturated NaCl (1×100 mL), dried (MgSO4), and concentrated under reduced pressure. The crude product was washed with MeOH (2×10 mL) to give the title compound (1.5 g, 75%).

Aufarbeitung

  1. stirringStirring
  2. waitcontinued for another 30 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with saturated NaCl (1×100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. washThe crude product was washed with MeOH (2×10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-73fc9d4f007747b4bf4942bfc215e983
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354406B2

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