Water → HCID 57756607, compound

HRID 229063Notes

Reaction equation

HRID 229063 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([C:23]2[CH:24]=[N:25][NH:26][CH:27]=2)=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1.[H-].[Na+].[CH3:30]I.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([C:23]2[CH:24]=[N:25][N:26]([CH3:30])[CH:27]=2)=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57756374HCID 57756374, compound2×

Product 1

HCID 57756607HCID 57756607, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-[6-methyl-2-(1H-pyrazol-4-yl)-pyridin-3-yloxy]-quinoline (compound 434) (30 mg) was suspended in N,N-dimethylformamide (1 ml), 60% sodium hydride (9.9 mg) was added to the suspension, and the mixture was then stirred for 30 min. Methyl iodide (18 mg) was added to the reaction solution, and the mixture was stirred for one hr. Water was added to the reaction solution to stop the reaction, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using hexane-acetone to give the title compound (23 mg, yield 73%).

Workup

  1. stirringthe mixture was stirred for one hr
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-bb9dc3db671348bfb79e6be0488bcfca
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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