Methyl iodide → HCID 89648818, compound

HRID 1774536Notes

Reaction equation

HRID 1774536 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]([OH:10])=[CH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6]1.IC.[C:22](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]([O:10][CH3:22])=[CH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469362HCID 178469362, compound

Product 1

HCID 89648818HCID 89648818, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21.58 g of ethyl 1-(2-fluorobenzyl)-5-hydroxy-1H-pyrazole-3-carboxylate 1-1-2 (81.66 mmol, 1.0 eq) were dissolved in dry acetone. Then 10.17 mL of iodomethane (163.3 mmol, 2.0 eq) and 40.63 g of potassium carbonate (294 mmol, 3.6 eq) were added. The precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was partitioned between DCM and water, the aqueous layer was separated and extracted with DCM twice. The combined organic layers were dried over magnesium sulfate, filtered off and concentrated in vacuo to give 14.74 g (52.96 mmol, 65%) of the crude target compound that was used for the next transformation without further purification.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between DCM and water
  4. customthe aqueous layer was separated
  5. extractionextracted with DCM twice
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuo
  9. customto give 14.74 g (52.96 mmol, 65%) of the crude target compound that
  10. customwas used for the next transformation without further purification

Sources & evidence

ORD record
ord-d0673e4ecd334a3d934b145c1728a509
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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