Methyl iodide → 5-Methoxy-7-methyl-3-(3-trifluoromethylphenyl)cinnoline

HRID 229732Notes

Reaction equation

HRID 229732 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:22])[C:5]2[CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[N:8]=[N:9][C:10]=2[CH:11]=1.CI.[C:25](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:25][O:22][C:4]1[CH:3]=[C:2]([CH3:1])[CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[N:8]=[N:9]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1354580247-Methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol

Product 1

HCID 230867125-Methoxy-7-methyl-3-(3-trifluoromethylphenyl)cinnolineYield 15.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an acetone solution (5 mL) of 7-methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol (30.4 mg, 0.1 mmol) obtained in Example 70 were added methyl iodide (0.006 mL, 0.11 mmol) and potassium carbonate (13.8 mg, 0.11 mmol), followed by reaction at room temperature over night. To residue obtained by concentration of the reaction liquid under reduced pressure was added distilled water (1 mL) and extracted with ethyl acetate. Residue obtained after concentration of an organic layer under reduced pressure was purified with silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain an objective compound (5 mg, 15%) as white solid.

Workup

  1. customfollowed by reaction at room temperature over night
  2. customTo residue obtained by concentration of the reaction liquid under reduced pressure
  3. additionwas added
  4. distillationdistilled water (1 mL)
  5. extractionextracted with ethyl acetate
  6. customResidue obtained after concentration of an organic layer under reduced pressure
  7. customwas purified with silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-71d04ee12efc4282aab2c31c6b5e221b
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Reaction notes

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