Sodium Hydroxide → HCID 178526791, compound

HRID 1943886Notes

Reaction equation

HRID 1943886 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4].[Br:15]Br>O1CCOCC1>[Br:15][C:14]1[C:8]2[C:9](=[N:10][CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=2)[NH:12][N:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 123527765-nitro-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178526791HCID 178526791, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4N NaOH (5.12 mL, 20.5 mmol) was added to a cold (0° C.) solution of 5-nitro-1H-pyrazolo[3,4-b]pyridine (0.84 g, 5.12 mmol) in dioxane (30 mL), followed by bromine (1.05 mL, 20.5 mmol). The cold bath was removed, and the reaction mixture was left at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and quenched with saturated Na2S2O3 (50 mL) The aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (9:1) to give 3-bromo-5-nitro-1H-pyrazolo[3,4-b]pyridine (1.10 g, 88%) as a solid.

Workup

  1. customThe cold bath was removed
  2. additionThe reaction mixture was diluted with ethyl acetate (100 mL)
  3. customquenched with saturated Na2S2O3 (50 mL) The aqueous layer
  4. extractionwas extracted with ethyl acetate (100 mL)
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography
  9. washeluting with hexanes/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-d257f01ec62249d69aa8daea52b29f83
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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