Triacetoxyperiodinane → HCID 117770350, compound

HRID 1526341Notes

Reaction equation

HRID 1526341 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13]([CH2:14][OH:15])=[CH:12][C:11]2[NH:16][N:17]=[C:18]([N:19]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])[C:10]=2[C:9]1=[O:30].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[NH:16][N:17]=[C:18]([N:19]3[C:20](=[O:29])[C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]3=[O:28])[C:10]=2[C:9]1=[O:30]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 117770562HCID 117770562, compound

Product 1

HCID 117770350HCID 117770350, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(5-(2-chlorophenyl)-6-(hydroxymethyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-1H-isoindole-1,3(2H)-dione obtained in Step I (317 mg), Dess-Martin periodinane (351 mg) and dichloromethane (7.53 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. to give the title compound (311 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59e75db8a8bc44bf8765ba449855ef48
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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