Iodine → HCID 178477913, compound

HRID 879650Notes

Reaction equation

HRID 879650 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[K+].[I:13]I>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([I:13])=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 202548685-Chloro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 178477913HCID 178477913, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-chloro-1H-pyrazolo[4,3-b]pyridine (100 mg, 0.65 mmol) in DMF (5 mL), was added KOH (91 mg, 1.63 mmol), I2 (247 mg, 0.98 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 5 min and then stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and water. The organic phase was washed by sat. NaHSO3, dried over MgSO4, filtered, concentrated, and purified by silica gel column, eluting by 0-70% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C6H3ClIN3: 279.9 (M+H+); Found: 279.3 (M+H+).

Workup

  1. stirringstirred at room temperature overnight
  2. washThe organic phase was washed by sat. NaHSO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column
  7. washeluting by 0-70% EtOAc in hexanes
  8. customto give the product

Sources & evidence

ORD record
ord-b3919bc976f44551b307bbbd4ecfe39c
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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