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

HRID 57970

Reaction equation

HRID 57970 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 867071531-[6-Fluoro-4-(oxetan-3-yl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridineYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-06e3421f661e4e9c99726d3e1ba1be4a
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Linked notes

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