Methyl iodide → HCID 69156810, compound

HRID 750145Notes

Reaction equation

HRID 750145 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30](=[O:33])(=[O:32])[NH2:31])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].[C:34](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([S:30](=[O:33])(=[O:32])[NH:31][CH3:34])=[CH:28][CH:29]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10128635HCID 10128635, compound

Product 1

HCID 69156810HCID 69156810, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-2-(4-sulfamoylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (264 mg), potassium carbonate (152 mg), methyl iodide (34 μl) and dimethylformamide (DMF) (5 ml) was stirred at room temperature for 5 hrs. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative HPLC to give the title compound (83 mg, 31%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-575f939b148f4e18beaa8cc41e9dcd12
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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