Ethyl Acetate → 4-(4-Aminophenoxy)-6-cyano-7-((2R)-oxiran-2-yl)methoxyquinoline

HRID 1433722Notes

Reaction equation

HRID 1433722 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:35][C@H:36]2[CH2:38][O:37]2)(=O)=O)=CC=1.C(OCC)(=O)C>CN(C)C=O.O>[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:35][C@H:36]4[CH2:38][O:37]4)=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 154187Glycidyl tosylate, (R)-HCID 1358293904-(4-Aminophenoxy)-6-cyano-7-hydroxyquinoline

Product 1

HCID 865914804-(4-Aminophenoxy)-6-cyano-7-((2R)-oxiran-2-yl)methoxyquinolineYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After dissolving 4-(4-aminophenoxy)-6-cyano-7-hydroxyquinoline (277 mg, 1.00 mmol) in dimethylformamide (3.0 ml), sodium hydride (40 mg, 1.00 mmol, 60% in oil) was added at room temperature and the mixture was stirred. There was then added (2R)-oxiran-2-ylmethyl 4-methyl-1-benzenesulfonate (228 mg, 1.00 mmol), and the mixture was heated and stirred at 60° C. for 5 hours. After cooling to room temperature, the reaction solution was distributed between ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the title compound (322 mg, 0.97 mmol, 97%) as a yellow solid.

Workup

  1. additionwas added at room temperature
  2. stirringstirred at 60° C. for 5 hours
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-7b0ae9c2e48d4cb2a6f6a9d3a00c8d41
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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