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

HRID 1778796Notes

Reaction equation

HRID 1778796 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]N1C(=O)CCC1=O>CN(C)C=O>[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

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

Product 1

HCID 1784778336-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridineYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (0.3 g, 2 mmol) (Frontier Cat. No. Z13659) and N-iodosuccinimide (0.53 g, 2.3 mmol) in N,N-dimethylformamide (2 mL) was stirred at 80° C. for 1 h. After cooling it was concentrated and the residue was treated with methanol. The white solid was collected by filtration to afford the desired product (0.5 g). LCMS (M+H)+=279.9.

Workup

  1. temperatureAfter cooling it
  2. concentrationwas concentrated
  3. additionthe residue was treated with methanol
  4. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-12f482c3b7c94b11b72b6c1d15d442df
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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