Methyl iodide → HCID 67130206, compound

HRID 2174542Notes

Reaction equation

HRID 2174542 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.[C:14]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.CCOC(C)=O>[CH3:14][O:13][C:11]1[CH:10]=[N:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=1

Participants

6

Reactant 3

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

Product 1

HCID 67130206HCID 67130206, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-1H-pyrazol-4-ol (Intermediate 4) (3.5 g, 20.1 mmol) and Cs2CO3 (8 g, 24.6 mmol) in DMF (100 mL) was added MeI (2 mL, 32 mmol). After stirring at room temperature for 2 h, the reaction mixture was diluted with EtOAc, washed with ice/brine. The aqueous was extracted with EtOAc, the combined organic solvents were removed under reduced pressure and the residue was purified by flash chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 60:40 as eluant) to give the title compound 4-(methyloxy)-1-(phenylmethyl)-1H-pyrazole (2.5 g, 13.3 mmol, 63% yield) as a yellow oil. LCMS: (M+H)+=189; Rt=0.81 min.

Workup

  1. washwashed with ice/brine
  2. extractionThe aqueous was extracted with EtOAc
  3. customthe combined organic solvents were removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 60:40 as eluant)

Sources & evidence

ORD record
ord-32f93af7bf6f4ab594733f772c945480
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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