Methyl iodide → HCID 66643823, compound

HRID 1695386Notes

Reaction equation

HRID 1695386 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].[C:25](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:25])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 666438345-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 66643823HCID 66643823, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester (1.37 g, 4.1 mmol) in DMF (10 mL) at room temperature was added cesium carbonate (1.35 g, 4.1 mmol) and methyliodide (587 mg, 0.26 mL, 4.1 mmol) and the resulting mixture stirred for 30 min. The resulting mixture was then evaporated and extracted with ethyl acetate and water. The organic extract was then washed with water, brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=4:1 to 2:3) afforded the title compound (730 mg, 51%) which was obtained as a colorless oil. MS: m/e=346.1 [M+H]+.

Workup

  1. customThe resulting mixture was then evaporated
  2. extractionextracted with ethyl acetate and water
  3. extractionThe organic extract
  4. washwas then washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by chromatography (silica, heptane:ethyl acetate=4:1 to 2:3)

Sources & evidence

ORD record
ord-7f69dce5263e49978f2127da12604b7d
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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