Sodium Iodide → (4-(7-chloro-1-(2,6-difluorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetonitrile

HRID 2206151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2206151
[Cl:1][C:2]1[C:3]2[N:12]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[N:11]=[C:10]([C:21]3[CH:22]=[C:23]([CH2:26][C:27]#[N:28])[S:24][CH:25]=3)[C:4]=2[C:5]([O:8]C)=[N:6][CH:7]=1.[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:1][C:2]1[C:3]2[N:12]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[N:11]=[C:10]([C:21]3[CH:22]=[C:23]([CH2:26][C:27]#[N:28])[S:24][CH:25]=3)[C:4]=2[C:5](=[O:8])[NH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 117988466(4-(7-chloro-1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetonitrile

Produkt 1

HCID 137010632(4-(7-chloro-1-(2,6-difluorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetonitrileAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of (4-(7-chloro-1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetonitrile (70.2 mg) and sodium iodide (50.5 mg) in acetonitrile (3 mL) was added chloro(trimethyl)silane (0.108 mL) at room temperature, and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, methanol/ethyl acetate) to give the title compound (38.1 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (basic silica gel, methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e2e62e03683046dfa295c3faefd90c10
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371320B2

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