Methyl iodide → HCID 86721227, compound

HRID 1750386Notes

Reaction equation

HRID 1750386 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20]I>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH3:20])[N:10]=[CH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178469915HCID 178469915, compound

Product 1

HCID 86721227HCID 86721227, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-fluorophenyl)-1H-pyrazole-4-carboxylate (15.0 g, 64.0 mmol) in THF was added sodium hydride (55 wt % paraffin oil, 3.35 g, 77.0 mmol) at room temperature and methyl iodide (8.01 mL, 128 mmol) was successively added at room temperature. After stirring at room temperature for 15 min, the reaction mixture was poured into ice water. The mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent; 33% ethyl acetate/hexane) to give a mixture (1:1 (mol/mol), 14.2 g, 90%) of ethyl 5-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carboxylate and ethyl 3-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carboxylate as a brown oil.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent; 33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c1553e038b6a4bfb9932cc40ca47fd27
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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