Triacetoxyperiodinane → HCID 86691838, compound

HRID 1616225Notes

Reaction equation

HRID 1616225 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[N:6]([CH3:23])[C:5]1=[O:24].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[N:6]([CH3:23])[C:5]1=[O:24]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86691839HCID 86691839, compound

Product 1

HCID 86691838HCID 86691838, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a microwave vial, 2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-(hydroxymethyl)benzonitrile (15-3) (300 mg, 0.86 mmol) and Dess-Martinperiodinane (545 mg, 1.28 mmol) was added under nitrogen and dissolved in DCM (4.3 ml). After stirring for 2 hours, the reaction was diluted with sodium thiosulfate, washed with DCM (3×), and then washed the combined organic layer with brine, dried over sodium sulfate, filtered and concentrated. The mixture was diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-formylbenzonitrile (30-1). MS (M+H)+: observed=349.2, calculated=349.4.

Workup

  1. washwashed with DCM (3×)
  2. washwashed the combined organic layer with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe mixture was diluted with methanol
  7. custompassed through a syringe
  8. filtrationfilter
  9. customThe solution was purified
  10. customthe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9436f5ae3d324d77b72c3c674c46c592
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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