Iodine → HCID 178506573, compound

HRID 1527288Notes

Reaction equation

HRID 1527288 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1.[I:10]I.[OH-].[K+]>CN(C=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+].O>[I:10][C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:1][N:2]=1

Participants

7

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 64514411H-Pyrazolo[3,4-c]pyridine

Product 1

HCID 178506573HCID 178506573, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of 1H-pyrazolo[3,4-c]pyridine [27]-47-6] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3×) with EtOAc. The combined organic extracts were washed with brine, then dried (Phase separator) and concentrated under vacuum. MS (LC/MS): 246.0 [M+H]+; tR (HPLC conditions k): 0.48 min.

Workup

  1. extractionextracted (3×) with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. customdried (Phase separator)
  4. concentrationconcentrated under vacuum
  5. custom0.48 min.

Sources & evidence

ORD record
ord-f49aefaa68e24ca3afbfdffe5c0573bd
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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