Methyl iodide → HCID 67130206, compound

HRID 1488139Notes

Reaction equation

HRID 1488139 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([OH:13])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC.[C:16]([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([N:8]1[CH:12]=[C:11]([O:13][CH3:16])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 6422181-benzyl-1H-pyrazol-4-ol2×

Product 1

HCID 67130206HCID 67130206, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 1-benzyl-1H-pyrazol-4-ol (compound 244.2, 1.40 g, 8.04 mmol) in N,N-dimethylformamide (20 mL). Iodomethane (703 μL, 11.3 mmol) and Cs2CO3 (3.68 g, 11.3 mmol,) were added and the resulting mixture was stirred for 3 h at room temperature. The mixture was concentrated under reduced pressure, then diluted with EtOAc (200 mL). The mixture was washed with brine (3×80 mL), and the organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the title compound as a yellow oil (1.30 g, 86%).

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with EtOAc (200 mL)
  4. washThe mixture was washed with brine (3×80 mL)
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30bb9d456b5d49d1a5c40c622adca1c2
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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