Potassium Cyanide → 1H-pyrazolo[3,4-b]pyridine-4-carbonitrile

HRID 888127Notes

Reaction equation

HRID 888127 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.C1(C)C=CC(S(O)=O)=CC=1.[Na].[C-:22]#[N:23].[K+]>CS(C)=O.O>[NH:8]1[C:4]2[N:5]=[CH:6][CH:7]=[C:2]([C:22]#[N:23])[C:3]=2[CH:10]=[N:9]1

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 10818p-Toluenesulfinic acidHCID 5360545SodiumHCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 694345511H-pyrazolo[3,4-b]pyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4-Iodo-1H-pyrazolo[3,4-b]pyridine (802 mg, 3.27 mmol) was dissolved in DMSO (10 mL) then added p-toluenesulfinic acid, sodium salt (583 mg, 3.27 mmol) and KCN (319 mg, 4.90 mmol). The reaction was heated at 100° C. for 18 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4 to yield 1H-pyrazolo[3,4-b]pyridine-4-carbonitrile as a light orange solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-10ad59d1faea44eea63578b42f319edf
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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