HCID 19712410, compound → HCID 67459825, compound

HRID 2366490Notes

Reaction equation

HRID 2366490 reaction equation
[Br-:1].[Br-:2].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][C:23]1([CH3:33])[CH2:31][C:30]2[NH:29][N:28]=[CH:27][C:26]=2[C:25](=[O:32])[CH2:24]1>C(O)(=O)C>[Br:1][C:24]1([Br:2])[C:23]([CH3:33])([CH3:22])[CH2:31][C:30]2[NH:29][N:28]=[CH:27][C:26]=2[C:25]1=[O:32]

Participants

4

Reactant 2

HCID 19712410HCID 19712410, compoundHCID 21124087Pyridiniumtribromide

Product 1

HCID 67459825HCID 67459825, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

According to Scheme 2 Step 3: Pyridinium tribromide (15.2 mmol, 4.87 g) was added to a solution of 6,6-dimethyl-6,7-dihydro-1H-indazol-4(5H)-one (6.09 mmol, 1.00 g) in acetic acid (9 mL) and the reaction mixture was heated under reflux for 3 hours. After evaporation of the solvent, the crude residue was partitioned between DCM and a saturated solution of Na2CO3. The organic phase was washed with water, was dried over Na2SO4 and concentrated to yield 5,5-dibromo-6,6-dimethyl-6,7-dihydro-1H-indazol-4(5H)-one (6.09 mmol, 1.96 g, 100%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter evaporation of the solvent
  4. customthe crude residue was partitioned between DCM
  5. washThe organic phase was washed with water
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bc06dbaa5bb94ab0a01e5c1d588a4567
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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