Methyl iodide → Methyl 5-iodo-1-methyl-1H-pyrazole-3-carboxylate

HRID 1046090Notes

Reaction equation

HRID 1046090 reaction equation
[I:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10]C)=[O:8])[NH:4][N:3]=1.[C:12]([O-])([O-])=O.[K+].[K+].[CH3:18][I:19]>CC#N>[I:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:12])[N:3]=1.[I:19][C:18]1[N:3]([CH3:2])[N:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469149HCID 178469149, compound

Product 2

HCID 46835547Methyl 5-iodo-1-methyl-1H-pyrazole-3-carboxylateHCID 58485356HCID 58485356, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-iodo-1H-pyrazole-5-carboxylate (600 mg, 2.56 mmol) and K2CO3 (609 mg, 4.51 mmol) in dry CH3CN (10 mL) was added MeI (974 mg, 6.77 mmol). The mixture was stirred at room temperature overnight under N2. After TLC showed that starting material had disappeared, the solid was filtered. Solvent was removed and the residue was purified to give methyl 3-iodo-1-methyl-1H-pyrazole-5-carboxylate and methyl 5-iodo-1-methyl-1H-pyrazole-3-carboxylate.

Workup

  1. filtrationthe solid was filtered
  2. customSolvent was removed
  3. customthe residue was purified

Sources & evidence

ORD record
ord-5c4af730fc4c4038948decb4ea30eda5
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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