Bromine → HCID 178419491, compound

HRID 1943864Notes

Reaction equation

HRID 1943864 reaction equation
[Br:1]Br.[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[N:4]1>C(Cl)(Cl)Cl>[Br:1][C:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:3][N:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 27558501H-pyrazolo(3,4-b)pyridine

Product 1

HCID 178419491HCID 178419491, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (1.91 mL, 37.1 mmol) was added dropwise to a solution of 1H-pyrazolo[3,4-b]pyridine (2.6 g, 21.8 mmol) in CHCl3 (100 mL), and the reaction mixture was left at room temperature overnight. The reaction mixture was concentrated, and the resulting residue was taken up in ethyl acetate (200 mL) and saturated NaHCO3 (50 mL) The aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were dried, filtered and concentrated to give 3-bromo-1H-pyrazolo[3,4-b]pyridine (3.7 g, 86%) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionsaturated NaHCO3 (50 mL) The aqueous layer was extracted with ethyl acetate (50 mL)
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a1f657b8ba84ca3be9f67521c7a9bda
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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