Water → HCID 178504858, compound

HRID 1500861Notes

Reaction equation

HRID 1500861 reaction equation
[CH3:1][S:2][C:3]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[NH:5][N:4]=1.[OH:12]OS([O-])=O.[K+].[OH2:18]>CN(C=O)C>[CH3:1][S:2]([C:3]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[NH:5][N:4]=1)(=[O:12])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 899242963-(methylthio)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 178504858HCID 178504858, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (10 g, 60.6 mmol) in DMF (100 mL) was added oxone (37 g, 121.2 mmol.) in portions. The reaction mixture was stirred at RT. After the reaction completed, water (100 mL) was added. The reaction was quenched carefully by addition of Na2SO3 and Na2CO3. The solid was filtered off and washed with MeOH (300 mL). The filtrate was concentrated under vacuum and the residue was purified by chromatography on silica gel column (DCM/MeOH=20/1) to give 3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (10.7 g, yield: 90%) as a yellow solid. MS obsd. (ESI+) [(M+H)+] 198.0.

Workup

  1. customThe reaction was quenched carefully by addition of Na2SO3 and Na2CO3
  2. filtrationThe solid was filtered off
  3. washwashed with MeOH (300 mL)
  4. concentrationThe filtrate was concentrated under vacuum
  5. customthe residue was purified by chromatography on silica gel column (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-c09b0dfd6730461fa0fd6fd984cfbd7c
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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