N-Iodosuccinimide → HCID 178497685, compound

HRID 272018Notes

Reaction equation

HRID 272018 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([O:15][CH3:16])=[O:14])[CH:9]=[C:4]2[CH:3]=[N:2]1.C1C(=O)N([I:27])C(=O)C1>ClC(Cl)C>[I:27][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([O:15][CH3:16])=[O:14])[CH:9]=2)[NH:1][N:2]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 59836056methyl 3-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate

Product 1

HCID 178497685HCID 178497685, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate (1.65 g, 6.52 mmol) in dichloroethane (40 mL) was added NIS (1.81 g, 8.04 mmol) and the mixture was stirred at 70° C. for 6 hours. The solvent was removed by reduced pressure and the crude product was purified by silica gel chromatography to afforded methyl 3-(3-iodo-1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate (9) (988 mg, 40% yield). MS: m/z 379.9 (M+H+).

Workup

  1. customThe solvent was removed by reduced pressure
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-45b0a74bb47d45bc825f3e32df467c9f
Source dataset
uspto-grants-2008_11
Patent number
US07452993B2

Reaction notes

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