Isopropyl iodide → HCID 58356347, compound

HRID 244628Notes

Reaction equation

HRID 244628 reaction equation
[CH:1]([C:3]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[NH:5][N:4]=1)=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:22]([CH3:24])[CH3:23]>C(#N)C>[CH:1]([C:3]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:5]([CH:22]([CH3:24])[CH3:23])[N:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 10796Cesium carbonateHCID 178450738HCID 178450738, compound

Product 1

HCID 58356347HCID 58356347, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1-Dimethylethyl 3-formyl-1H-pyrazole-5-carboxylate (600 mg) and cesium carbonate (996 mg) were dissolved in acetonitrile (60 ml). 2-Iodopropane (0.305 ml) was added and the mixture was stirred at RT for 20 h. A further portion of 2-iodopropane (0.03 ml) was added and the mixture was stirred at RT for 16 h. The solvent was removed in vacuo. The reaction mixture was diluted with water (80 ml) and DCM (80 ml) and separated using a hydrophobic frit. The aqueous layer was extracted with a further quantity of DCM (2×50 ml) using a hydrophobic frit. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel (50 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound (377 mg), and a mixture (213 mg) of both isomers. The mixture was purified by flash chromatography on silica gel (20 g silica), eluting with a gradient of 0-50% ethyl acetate in cyclohexane to give another quantity (114 mg) of the title compound (114 mg) as a colourless oil.

Workup

  1. stirringthe mixture was stirred at RT for 16 h
  2. customThe solvent was removed in vacuo
  3. additionThe reaction mixture was diluted with water (80 ml) and DCM (80 ml)
  4. customseparated
  5. extractionThe aqueous layer was extracted with a further quantity of DCM (2×50 ml)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography on silica gel (50 g silica)
  8. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-4538af017d344996854846cbbbdb31c5
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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