Triacetoxyperiodinane → HCID 69507078, compound

HRID 1623134Notes

Reaction equation

HRID 1623134 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:25]=[CH:26][C:27]2[C:28]3[N:36]([CH2:37][CH2:38][CH2:39][CH:40]([OH:42])[CH3:41])[C:35]([CH2:43][CH2:44][CH3:45])=[N:34][C:29]=3[CH:30]=[N:31][C:32]=2[CH:33]=1>ClCCl.S([O-])([O-])=S.[Na+].[Na+]>[Br:23][C:24]1[CH:25]=[CH:26][C:27]2[C:28]3[N:36]([CH2:37][CH2:38][CH2:39][C:40](=[O:42])[CH3:41])[C:35]([CH2:43][CH2:44][CH3:45])=[N:34][C:29]=3[CH:30]=[N:31][C:32]=2[CH:33]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69507061HCID 69507061, compound

Product 1

HCID 69507078HCID 69507078, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15847209sodium thiosulfite anhydrousSolvent

Procedure

Dess-Martin periodinan (3.51 g, 8.29 mmol) was added to a solution of 5-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-ol (2.6 g, 6.9 mmol) in dichloromethane and stirred overnight at ambient temperature. The reaction mixture was diluted with sodium thiosulfite (2×50 mL) and the layers were separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate (twice) and brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford 2.50 g of 5-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with saturated aqueous sodium bicarbonate (twice) and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7672ea6959344e5a8c48ca9be60cab1b
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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