Methyl iodide → Methyl 5-methyl-2-(1-methyl-1H-pyrazol-3-yl)benzoate

HRID 60917Notes

Reaction equation

HRID 60917 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:16]=[CH:15][NH:14][N:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH3:19]I>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:16]=[CH:15][N:14]([CH3:19])[N:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178497697HCID 178497697, compound

Product 1

HCID 117727908Methyl 5-methyl-2-(1-methyl-1H-pyrazol-3-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-methyl-2-(1H-pyrazol-3-yl)benzoate (0.16 g, 0.744 mmol) in DMF (3 mL) at rt was added NaH (60%, 0.081 g, 2.02 mmol) under argon protection. The mixture was stirred atrt for 1 h, and then MeI (0.07 mL, 1.116 mmol) was added. The resulting mixture was stirred for another 1 h. The solvent was removed in vacuo. The crude was dissolved with EtOAc and washed with satd. NaHCO3, brine, and dried (MgSO4). The solvent was removed and the crude was purified by silica gel chromatography to obtain the faster eluting methyl 5-methyl-2-(1-methyl-1H-pyrazol-5-yl)benzoate as the minor product and the slower eluting methyl 5-methyl-2-(1-methyl-1H-pyrazol-3-yl)benzoate as the title compound and major product. ESI-MS (m/z): 231 [M+1]+.

Workup

  1. stirringThe resulting mixture was stirred for another 1 h
  2. customThe solvent was removed in vacuo
  3. dissolutionThe crude was dissolved with EtOAc
  4. washwashed with satd
  5. dry with materialNaHCO3, brine, and dried (MgSO4)
  6. customThe solvent was removed
  7. customthe crude was purified by silica gel chromatography
  8. customto obtain the
  9. washfaster eluting methyl 5-methyl-2-(1-methyl-1H-pyrazol-5-yl)benzoate as the minor product
  10. washthe slower eluting methyl 5-methyl-2-(1-methyl-1H-pyrazol-3-yl)benzoate as the title compound and major product

Sources & evidence

ORD record
ord-fe6d265140d64ddea057bdb57597920d
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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