Sodium Thiosulfate → HCID 178520051, compound

HRID 1943923Notes

Reaction equation

HRID 1943923 reaction equation
[CH:1]1([CH:4]([C:6]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][N:7]=2)[OH:5])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(=O)(O)[O-]>[CH:1]1([C:4]([C:6]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][N:7]=2)=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 178520052cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanol

Product 1

HCID 178520051HCID 178520051, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 6344DichloromethaneSolvent

Procedure

Cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanol (200 mg, 1.06 mmol) was taken up in DCM (8 mL). Dess-Martin (0.448 g, 1.06 mmol) was added to this solution, which was stirred at room temperature for 10 minutes. A solution of 10% sodium thiosulfate in saturated aqueous bicarbonate was added and resulted in a biphasic solution, which was vigorously stirred for 30 minutes. The organic layers were extracted with DCM (3×10 mL), dried over sodium sulfate and concentrated. Chromatography (EtOAc) afforded cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanone (100 mg, 50.5%) as an oil, which crystallized upon standing.

Workup

  1. customresulted in a biphasic solution, which
  2. stirringwas vigorously stirred for 30 minutes
  3. extractionThe organic layers were extracted with DCM (3×10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-80856d4f76304506a8e205b906e91963
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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