Iodoethane → HCID 69155754, compound

HRID 750226Notes

Reaction equation

HRID 750226 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[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(=O)([O-])[O-].[K+].[K+].[CH2:37](I)[CH3:38]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:37][CH3:38])=[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 6340IodoethaneHCID 11430Potassium CarbonateHCID 69156619HCID 69156619, compound

Product 1

HCID 69155754HCID 69155754, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-bromo-2-(4-hydroxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (200 mg), potassium carbonate (89 mg) and DMF (4.0 ml) was added ethyl iodide (41 μl) at room temperature with stirring, and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1) to give the title compound (110 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1)

Sources & evidence

ORD record
ord-6a3ba70d0f6a4e1fbecb88af21c8b713
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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