Cesium carbonate → 1-[6-Fluoro-4-(oxetan-3-yl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine

HRID 57970

Reaktionsgleichung

Reaktionsgleichung von HRID 57970
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][NH:16][C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.[F:17][C:18]1[CH:23]=[C:22]([CH:24]2[CH2:27][O:26][CH2:25]2)[CH:21]=[C:20](F)[N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:17][C:18]1[N:19]=[C:20]([N:16]2[C:10]3[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[N:13]=[CH:12][C:11]=3[CH:14]=[N:15]2)[CH:21]=[C:22]([CH:24]2[CH2:27][O:26][CH2:25]2)[CH:23]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 867070806-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridineHCID 867071522,6-Difluoro-4-(oxetan-3-yl)pyridine

Produkt 1

HCID 867071531-[6-Fluoro-4-(oxetan-3-yl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridineAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.468 mmol; 98.9 mg) and 2,6-difluoro-4-(oxetan-3-yl)pyridine (0.468 mmol; 80.1 mg) in DMF (5 mL) was added Cesium carbonate (0.562 mmol; 183 mg). The resulting mixture was stirred at room temperature. The mixture was filtered. The filtrate was partitioned between EtOAc and water. The organic layer was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford 1-[6-fluoro-4-(oxetan-3-yl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine as a white solid (63.2 mg, 31%).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customThe filtrate was partitioned between EtOAc and water
  3. concentrationThe organic layer was concentrated
  4. customThe residue was purified on silica
  5. washeluted with 0 to 6% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-06e3421f661e4e9c99726d3e1ba1be4a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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