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

HRID 853587Notes

Reaction equation

HRID 853587 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-b4d4286e3e2c49a3acfce4b63cc98300
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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