Isopropyl iodide → HCID 19576656, compound

HRID 244617Notes

Reaction equation

HRID 244617 reaction equation
[NH:1]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:17]([CH3:19])[CH3:18]>C(#N)C>[CH3:18][CH:17]([N:1]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=[N:2]1)[CH3:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 565662Methyl 1H-pyrazole-3-carboxylate

Product 1

HCID 19576656HCID 19576656, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 1H-pyrazole-5-carboxylate (0.6 g) (available from Fluorochem), in acetonitrile (50 ml) was added cesium carbonate (1.55 g) followed by 2-iodopropane (0.476 ml) and the mixture stirred at 20° C. for 18 h. The solvent was removed in vacuo and the residue was partitioned between water (20 ml) and DCM (20 ml) and separated by hydrophobic frit. Purification by chromatography on silica gel (50 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane gave methyl 1-(1-methylethyl)-1H-pyrazole-5-carboxylate (0.24 g) as a colourless oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water (20 ml) and DCM (20 ml)
  3. customseparated by hydrophobic frit
  4. customPurification by chromatography on silica gel (50 g silica)
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-f3a23d5d3704484dbbcdf7f5ced38f3c
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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