Methyl iodide → HCID 57899237, compound

HRID 1802791Notes

Reaction equation

HRID 1802791 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:6]([CH3:17])=[N:7][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]=1[OH:10].[CH3:19][O:20][C:21](=[O:36])[CH2:22][CH:23]1[C:27](=[O:28])[N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:25]=[C:24]1[CH3:35].[C:37]([O-])([O-])=O.[K+].[K+].CI>C(#N)C.O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:6]([CH3:17])=[N:7][N:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:9]=1[O:10][CH3:19].[CH3:19][O:20][C:21](=[O:36])[CH2:22][C:23]1([CH3:37])[C:27](=[O:28])[N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:25]=[C:24]1[CH3:35].[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:7]([CH3:19])[C:6]=1[CH3:17]

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24217929HCID 24217929, compoundHCID 178499522HCID 178499522, compound

Product 3

HCID 57899229HCID 57899229, compoundYield 12%HCID 57899237HCID 57899237, compoundYield 58%HCID 57899248HCID 57899248, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of (5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-acetic acid methyl ester and (3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester (678 mg, 2.75 mmol), K2CO3 (pulverized, 1.45 g, 10.5 mmol), and methyl iodide (0.7 mL, 11 mmol) in acetonitrile 10 mL) was refluxed for 1 h and cooled to room temperature. The reaction mixture was diluted with water (40 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via silica gel column chromatography to give (5-methoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-acetic acid methyl ester (86.5 mg, 12%), (3,4-dimethyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester (161 mg, 22%) and (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester (417 mg, 58%). LCMS 261.2 (M+1).

Workup

  1. temperaturewas refluxed for 1 h
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-ac3eecd11bbb46889e1863f5d012f65b
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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