Methyl iodide → 2-(2-Methyl-5-phenyl-pyrazol-3-yl)isoindoline-1,3-dione

HRID 588638Notes

Reaction equation

HRID 588638 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:13]=[C:12]([N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])[NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:25]I>CN(C=O)C.O>[CH3:25][N:11]1[C:12]([N:14]2[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])=[CH:13][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:10]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178514955HCID 178514955, compound

Product 1

HCID 867173302-(2-Methyl-5-phenyl-pyrazol-3-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (830 mg, 0.02 mol) was added portionwise to a mixture of 2-(3-phenyl-1H-pyrazol-5-yl)isoindoline-1,3-dione (5 g, 0.0173 mol) and methyl iodide (1.5 mL, 0.024 mol) in DMF (80 mL) at 10° C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water and the aqueous phase was extracted with ethyl acetate twice. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:19 to 2:8) yielding a mixture of the title compound and the regioisomer 2-(2-methyl-5-phenyl-pyrazol-3-yl)isoindoline-1,3-dione (850 mg, 5:1).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate twice
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:19 to 2:8)
  6. customyielding

Sources & evidence

ORD record
ord-9471b3d236d64294881d709b7e704f0d
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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