Water → Propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]-pyridin-3-yl)-hydroxy-methyl]-2-fluoro-phenyl}-amide

HRID 1098410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098410
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[F:11][C:12]1[C:17]([CH:18]=[O:19])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22].[OH-].[K+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:18]([OH:19])[C:17]3[C:12]([F:11])=[C:13]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[CH:14]=[CH:15][CH:16]=3)=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 58086814Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide

Produkt 1

HCID 58086504Propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]-pyridin-3-yl)-hydroxy-methyl]-2-fluoro-phenyl}-amideAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 5-bromo-7-azaindole 67 (312 mg, 1.58 mmol) in methanol (28 mL) were added propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide (503, 370 mg, 1.5 mmol) and potassium hydroxide (422.8 mg, 7.5 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the desired compound as white solid (504, 300 mg, 45.0%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-3eb88908fb134cca852eff5c94fb7bf6
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143271B2

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