Methyl iodide → HCID 68498888, compound

HRID 1594106Notes

Reaction equation

HRID 1594106 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[N:7]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[N:8]=[CH:9][CH:10]=1)[CH3:2].CI.[C:19](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:6]1[N:7]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[N:8]=[CH:9][CH:10]=1)[CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 68497561HCID 68497561, compound

Product 1

HCID 68498888HCID 68498888, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2-thiazol-2-yl-2H-pyrazol-3-yl)-acetic acid ethyl ester (100 mg, 0.42 mmol), methyl iodide (66 mg, 0.46 mmol) and cesium carbonate (151 mg, 0.46 mmol) in DMF (6 mL) is stirred at room temperature overnight. The reaction is quenched with NH4Cl (aq.) (6 mL) and ethyl acetate (30 mL). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (3×30 mL). The combined organic layers are dried and the solvent removed. The crude is purified by PTLC (hexane/ethyl acetate 3:1) to give 2-(2-thiazol-2-yl-2H-pyrazol-3-yl)-propionic acid ethyl ester as an oil.

Workup

  1. customThe reaction is quenched with NH4Cl (aq.) (6 mL) and ethyl acetate (30 mL)
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (3×30 mL)
  4. customThe combined organic layers are dried
  5. customthe solvent removed
  6. customThe crude is purified by PTLC (hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-c714fec7a5c84d2b815cd0f6b53f4bab
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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