Sodium hydride → 7-(5-Bromo-2-chloropyrimidin-4-yloxy)quinoline

HRID 449860Notes

Reaction equation

HRID 449860 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:14][C:15]1[C:16](Cl)=[N:17][C:18]([Cl:21])=[N:19][CH:20]=1>CN(C)C=O.ClCCl.CO>[Br:14][C:15]1[C:16]([O:11][C:8]2[CH:9]=[C:10]3[C:5]([CH:4]=[CH:3][CH:2]=[N:1]3)=[CH:6][CH:7]=2)=[N:17][C:18]([Cl:21])=[N:19][CH:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 1354268667-Hydroxyquinoline

Product 1

HCID 866481627-(5-Bromo-2-chloropyrimidin-4-yloxy)quinoline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

In a 4 mL vial was charged with quinolin-7-ol (0.200 g, 1.378 mmol) and sodium hydride (0.066 g, 1.653 mmol) in N,N-dimethylformamide (13.78 ml) to give a brown solution. The reaction was stirred at room temperature for 30 minutes and then 5-bromo-2,4-dichloropyrimidine (0.176 mL, 1.378 mmol) was added. The mixture was stirred at room temperature overnight. Diluted with 9:1 dichloromethane/methanol; washed with water and brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure to afford a tan residue. (ESI(+)) m/e 337.7 (M+H)+.

Workup

  1. customto give a brown solution
  2. stirringThe mixture was stirred at room temperature overnight
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customto afford a tan residue

Sources & evidence

ORD record
ord-39bd615cf9064c51b243086498594065
Source dataset
uspto-grants-2013_07
Patent number
US08486933B2

Reaction notes

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