Mesna → 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine

HRID 1500860Notes

Reaction equation

HRID 1500860 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(S)[CH2:12][S:13]([O-])(=O)=O.[Na+]>CS(C)=O.[Cu]I>[CH3:12][S:13][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 2

HCID 23662354MesnaHCID 178506573HCID 178506573, compound

Product 1

HCID 899242963-(methylthio)-1H-pyrazolo[3,4-c]pyridineYield 50%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-iodo-1H-pyrazolo[3,4-c]pyridine 3 (9.5 g, 38.8 mmol) in DMSO (20 mL) was added aq. MeSNa (wt. 20%, 40 mL, 116 mmol), followed by CuI (270 mg, 1.94 mmol). The mixture was degassed and refilled with nitrogen. The reaction was heated at 150° C. overnight. After cooled to RT, the volatiles were removed and the residue was purified by column (PE/EtOAc=2/1 to 1/1) to give 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (3.2 g, yield: 50%) as a yellow solid. MS obsd. (ESI+) [(M+H)+] 166.0.

Workup

  1. customThe mixture was degassed
  2. additionrefilled with nitrogen
  3. temperatureAfter cooled to RT
  4. customthe volatiles were removed
  5. customthe residue was purified by column (PE/EtOAc=2/1 to 1/1)

Sources & evidence

ORD record
ord-96a99c84e591466a9f8f22c80bb62121
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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