N-Iodosuccinimide → 6-(3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-b]pyridine

HRID 1778767Notes

Reaction equation

HRID 1778767 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[NH:19][N:18]=[CH:17][C:14]3=[N:15][CH:16]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[I:20]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[CH:12]=[C:13]3[NH:19][N:18]=[C:17]([I:20])[C:14]3=[N:15][CH:16]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 867228626-(3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1784934406-(3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-b]pyridineYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At r.t. to a solution of 6-(3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-b]pyridine (0.38 g, 1.5 mmol) in methylene chloride (5 mL) was added N-iodosuccinimide (0.352 g, 1.56 mmol) with stirring. The mixture was stirred at r.t. overnight. Then the solvent was removed, the residue was treated with methanol. The solid was collected by filtration to afford the desired product (0.54 g) which was directly used in next step reaction without further purification. LCMS (M+H)+=382.1.

Workup

  1. stirringThe mixture was stirred at r.t. overnight
  2. customThen the solvent was removed
  3. additionthe residue was treated with methanol
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-6f1f007be5fa4717a6fb2430a0f2221c
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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