Methyl iodide → 2-Benzyl-5,1',5'-trimethyl-2'-phenyl-1',2'-dihydro-2H-[3,4']bipyrazolyl-3'-one

HRID 555643Notes

Reaction equation

HRID 555643 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[C:17]([CH3:18])=[N:16][N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]=2[OH:25])=[CH:11][C:10]([CH3:26])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]([C:13]2[C:14](=[O:25])[N:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:16]([CH3:27])[C:17]=2[CH3:18])=[CH:11][C:10]([CH3:26])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178422852HCID 178422852, compound

Product 1

HCID 669880082-Benzyl-5,1',5'-trimethyl-2'-phenyl-1',2'-dihydro-2H-[3,4']bipyrazolyl-3'-oneYield 21.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-benzyl-5,5′-dimethyl-2′-phenyl-2H,2′H-[3,4′]bipyrazolyl-3′-ol (Example 36, 0.200 g, 0.58 mmol) in DMF add cesium carbonate (0.944 g, 2.90 mmol), and then iodomethane (0.823 g, 5.8 mmol). Stir this mixture at room temperature overnight. Dilute the reaction mixture with ethyl acetate, wash with water (25 ml×5) and dry (sodium sulfate). Chromatograph on silica gel, eluting with 50-100% ethyl acetate/heptane to provide 0.045 g of the title compound.

Workup

  1. washwash with water (25 ml×5)
  2. dry with materialdry (sodium sulfate)
  3. washChromatograph on silica gel, eluting with 50-100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-72360ac46d4a4bbabb79c895c893f901
Source dataset
uspto-grants-2011_11
Patent number
US08053458B2

Reaction notes

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