Isopropanol → 3-Bromo-2-methyl-7-(2,4,6-trimethylphenyl)-2,4,5,7-tetrahydro-pyrazolo[3,4-b]pyridin-6-one

HRID 2113806Notes

Reaction equation

HRID 2113806 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Br:7][C:8]1[N:9]([CH3:26])[N:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][CH2:13][N:12]2[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25].C([OH:30])(C)C>O.C(Cl)(Cl)(Cl)Cl.O.[Ru](=O)=O>[Br:7][C:8]1[N:9]([CH3:26])[N:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][C:13](=[O:30])[N:12]2[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25]

Participants

7

Reactant 3

HCID 3776IsopropanolHCID 11232898HCID 11232898, compoundHCID 23667635Sodium periodate

Product 1

HCID 598115213-Bromo-2-methyl-7-(2,4,6-trimethylphenyl)-2,4,5,7-tetrahydro-pyrazolo[3,4-b]pyridin-6-one

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

Ruthenium(IV) oxide hydrate (22 mg) was dissolved in 35 mL water and sodium periodate (684 mg) was added. This mixture was rapidly stirred while 3-bromo-2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (1-3; 505 mg) in 25 mL carbon tetrachloride was added dropwise. After the mixture had stirred at room temperature over night, isopropanol was added and the mixture was stirred for an additional hour. The mixture was then filtered through diatomaceous earth and extracted with dichloromethane. The organic extracts were dried with magnesium sulfate and concentrated. The residue was chromatographed on silica gel to afford 54.4 mg of 3-bromo-2-methyl-7-(2,4,6-trimethylphenyl)-2,4,5,7-tetrahydro-pyrazolo[3,4-b]pyridin-6-one (9-4).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred for an additional hour
  3. filtrationThe mixture was then filtered through diatomaceous earth
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic extracts were dried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-7794c2062a0a4b7895b1b465a9c60919
Source dataset
uspto-grants-2008_10
Patent number
US07432283B2

Reaction notes

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