N-Iodosuccinimide → HCID 178419453, compound

HRID 1943868Notes

Reaction equation

HRID 1943868 reaction equation
[I:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]2[CH:18]=[N:17][NH:16][C:13]2=[N:14][CH:15]=1>ClC(Cl)C.C1COCC1>[Br:9][C:10]1[CH:11]=[C:12]2[C:18]([I:1])=[N:17][NH:16][C:13]2=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Product 1

HCID 178419453HCID 178419453, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Iodosuccinimide (8.1 g, 34.1 mmol) was added to a solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine (4.5 g, 22.7 mmol) in dichloroethane (100 mL), and the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and diluted with THF (300 mL). The organic layers were washed with saturated Na2S2O3 (100 mL) and brine (100 mL). The organic layers were dried, filtered and concentrated to a solid. The crude product was triturated with DCM and ethyl acetate to give 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine (5.5 g, 75%) as a solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. washThe organic layers were washed with saturated Na2S2O3 (100 mL) and brine (100 mL)
  4. customThe organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. customThe crude product was triturated with DCM and ethyl acetate

Sources & evidence

ORD record
ord-710d01e85c8c4d39a3d2fa6b6d3baaaa
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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