Iodine → 6-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine

HRID 588092Notes

Reaction equation

HRID 588092 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.[I:11]I.[OH-].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([I:11])=[N:9][NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 14797Potassium Hydroxide2×HCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

Product 1

HCID 1784778336-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A flask was charged with 6-chloro-1H-pyrazolo[4,3-c]pyridine (3.0 g, 19.54 mmol), iodine (13.11 g, 51.7 mmol), KOH (3.29 g, 58.6 mmol), and DMF (60 mL). The mixture was heated at 40° C. for 16 h and then additional iodine (7.8 g, 30.7 mmol) and KOH (1.6 g, 28.4 mmol) were added. The mixture was heated at 70° C. for 3 h then quenched with 1 N Na2S2O3 and extracted with EtOAc. The organic phase was washed with water, brine, and dried over Na2SO4. After evaporation of volatiles DCM was added. A solid precipitated and was collected by filtration to yield 6-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, which was carried onto the next step without further purification. MS ESI calc'd. for C6H4ClIN3 [M+1]+ 280. found 280.

Workup

  1. temperatureThe mixture was heated at 70° C. for 3 h
  2. customthen quenched with 1 N Na2S2O3
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of volatiles DCM
  7. additionwas added
  8. customA solid precipitated
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a8a699e356cb4f83bcfa6cda1d61b21b
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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