Methyl iodide → 7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester

HRID 2427510Notes

Reaction equation

HRID 2427510 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]([OH:26])=[O:25])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[C:27](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C>[CH3:27][O:25][C:24]([C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=1)[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=1)[CH2:7]2)=[O:26]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53311336HCID 53311336, compound

Product 1

HCID 579494347-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Methyl-1-oxo-2-(4-trifluoromethoxybenzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid (170.00 mg, 0.465 mmol) was mixed with potassium carbonate (193.0 mg, 1.40 mmol) and methyl iodide (199.0 mg, 1.40 mmol) in DMF (2.0 mL) over a weekend. The reaction mixture was diluted with ethyl acetate, and washed with water, brine, dried over sodium sulfate, filtered and concentrated to provide the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e76787b2d72b4e93aa6a2531743506b0
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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