Bromide ion → HCID 135458024, compound

HRID 229731

Reaction equation

HRID 229731 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]=[N:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:6][C:5]=2[C:4](=[O:22])[CH2:3]1.[Br-].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[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

Participants

5

Reactant 3

HCID 259Bromide ionHCID 516892Sodium BicarbonateHCID 100180127-methyl-3-(3-trifluoromethylphenyl)-7,8-dihydro-6H-cinnolin-5-one

Product 1

HCID 135458024HCID 135458024, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To an ethyl acetate solution (1 mL) of 7-methyl-3-(3-trifluoromethylphenyl)-7,8-dihydro-6H-cinnolin-5-one (306 mg, 1.0 mmol) obtained in Example 66 was added cupuric bromide (446 mg, 2.0 mmol), followed by reaction under heating and refluxing for 8 hours, adding saturated sodium bicarbonate aqueous solution (2 mL) to the reaction liquid and extraction with ethyl acetate. To residue obtained after concentration of an organic layer under reduced pressure was added ethyl acetate (1 mL) and filtered off solid obtained to get an objective product (17 mg, 5.5%) as yellow solid.

Workup

  1. customfollowed by reaction
  2. temperatureunder heating
  3. temperaturerefluxing for 8 hours
  4. customTo residue obtained after concentration of an organic layer under reduced pressure
  5. filtrationfiltered off solid
  6. customobtained

Sources & evidence

ORD record
ord-ff26126a4628438c9be7a02cf30b4270
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Linked notes

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