Acetic Acid → 5-Bromo-1H-pyrazolo[3,4-c]pyridine

HRID 1774953Notes

Reaction equation

HRID 1774953 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.C(O)(=O)C.[N:14]([O-])=O.[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[CH:9]=[N:14][NH:8][C:5]2=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 199260946-Bromo-4-methylpyridin-3-amineHCID 23668193Sodium Nitrite

Product 1

HCID 457897785-Bromo-1H-pyrazolo[3,4-c]pyridineYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-bromo-4-methylpyridin-3-amine (7.76 g, 0.0415 mol) in acetic acid (412.8 mL, 7.260 mol) was added Sodium nitrite (2.87 g, 0.0416 mol) in 4.0 ml water (Bioorg. Med. Chem. 15 (2007) 2441-2452). The reaction was stirred for 15 min and allowed to stand at room temperature (rt) for 2 days (d). The reaction was concentrated and diluted EtOAc then washed with NaHCO3 and brine. The organic layer was dried Na2SO4, filtered and concentrated. The crude was purified by chromatography (DCM/MeOH) eluted at 5% MeOH) to give 5-bromo-1H-pyrazolo[3,4-c]pyridine (79.1% yield)

Workup

  1. customto stand at room temperature
  2. custom(rt)
  3. customfor 2 days
  4. concentrationThe reaction was concentrated
  5. washdiluted EtOAc then washed with NaHCO3 and brine
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by chromatography (DCM/MeOH)
  9. washeluted at 5% MeOH)

Sources & evidence

ORD record
ord-4f0689e3da4546f09317eb72e7745177
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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