Imidazole → 5-(1H-imidazol-1-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine

HRID 1774981Notes

Reaction equation

HRID 1774981 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:8](C3CCCCO3)[C:5]2=[CH:6][N:7]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu]I>[N:23]1([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 866766845-bromo-3-phenyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712537055-(1H-imidazol-1-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 100.0 mg (0.2791 mmol) of 5-bromo-3-phenyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine, 47.51 mg (0.6979 mmol) of 1H-Imidazole, 53.16 mg (0.2791 mmol) of Copper(I) iodide, 30.04 uL (0.2791 mmol) of N,N′-dimethylethylenediamine and 363.8 mg (1.116 mmol) of Cesium Carbonate in 3 ml of N,N-Dimethylformamide was heated at 120° C. for 48 hours. The mixture was filtered, the filtrate concentrated in high vacuum and the residue partitioned between ethyl acetate and water. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated in vacuum. The residue was purified on 4 g of silica gel column, eluting 5-(1H-imidazol-1-yl)-3-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine with a gradient of ethyl acetate in heptane. Yield 67 mg (69%). ESI MS m/z 346.1 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated in high vacuum
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic extracts were washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified on 4 g of silica gel column
  8. washeluting 5-(1H-imidazol-1-yl)-3-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine with a gradient of ethyl acetate in heptane

Sources & evidence

ORD record
ord-744d7fd5dc9f42d7aed65407c2cee6cf
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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