Sodium Iodide → 4-((7-oxo-3-phenyl-6,7-dihydro-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamide

HRID 2206012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2206012
C[O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][N:9]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[C:8]=12.[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[O:2]=[C:3]1[C:8]2[N:9]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][NH:4]1

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 1179880834-((7-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamide

Produkt 1

HCID 1179880844-((7-oxo-3-phenyl-6,7-dihydro-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamideAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-((7-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamide (155 mg) in acetonitrile (30 mL) were added sodium iodide (118 mg) and chloro(trimethyl)silane (342 mg), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate). To the obtained residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate and hexane to give the title compound (147 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
  3. additionTo the obtained residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-b7d7ba020830409e93758fa78ed0972f
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371320B2

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