Chloromethyl Methyl Ether → HCID 69155538, compound

HRID 750227Notes

Reaction equation

HRID 750227 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+].[CH3:37][O:38][CH2:39]Cl>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][O:38][CH3:39])=[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 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 69156619HCID 69156619, compound

Product 1

HCID 69155538HCID 69155538, 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 methoxymethylchloride (39 μl) at room temperature with stirring, and the mixture was stirred at 50° C. for 12 hrs. After cooling the reaction mixture, the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water, and 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 (75 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 50° C. for 12 hrs
  2. temperatureAfter cooling the reaction mixture
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1)

Sources & evidence

ORD record
ord-6a6eecb26cc941d5b8164c3d76a94241
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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