Acetone → HCID 23086737, compound

HRID 229734Notes

Reaction equation

HRID 229734 reaction equation
CC(C)=O.[CH3:5][C:6]1[CH:7]=[C:8]([OH:26])[C:9]2[CH:10]=[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[N:12]=[N:13][C:14]=2[CH:15]=1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC.C(OCC)(=O)C>[CH2:27]([O:26][C:8]1[CH:7]=[C:6]([CH3:5])[CH:15]=[C:14]2[C:9]=1[CH:10]=[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[N:12]=[N:13]2)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7498Benzyl Bromide2×HCID 11430Potassium Carbonate2×HCID 1354580247-Methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol

Product 1

HCID 23086737HCID 23086737, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To an acetone solution (5 mL) of 7-methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol (69 mg, 0.2 mmol) obtained in Example 70 were added benzyl bromide (0.024 mL) and potassium carbonate (28 mg, 0.2 mmol), followed by stirring at room temperature over night and refluxing under heating for 3 hours. The reaction liquid was further added with benzyl bromide (0.024 mL) and potassium carbonate (28 mg, 0.2 mmol), followed by stirring at room temperature over night, concentration of the reaction liquid under reduced pressure, adding distilled water (1 mL), extraction with ethyl acetate and purification of residue obtained after concentration of an organic layer under reduced pressure, with HPLC column chromatography (hexane/ethyl acetate=3/1) to obtain an objective compound (8 mg, 10%).

Workup

  1. temperaturerefluxing
  2. temperatureunder heating for 3 hours
  3. customThe reaction liquid
  4. stirringby stirring at room temperature over night
  5. customconcentration of the reaction liquid under reduced pressure
  6. additionadding
  7. distillationdistilled
  8. extractionwater (1 mL), extraction
  9. customwith ethyl acetate and purification of residue
  10. customobtained after concentration of an organic layer under reduced pressure

Sources & evidence

ORD record
ord-9276c096a003408dbfcfd4dc29f5f592
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Reaction notes

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