Bromine → 5-Bromo-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

HRID 1263489Notes

Reaction equation

HRID 1263489 reaction equation
[Br:1]Br.[C:3]1([N:9]2[C:13]3[NH:14][C:15](=[O:18])[CH:16]=[CH:17][C:12]=3[CH:11]=[N:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(=O)C.O>[Br:1][C:16]1[C:15](=[O:18])[NH:14][C:13]2[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:10]=[CH:11][C:12]=2[CH:17]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 1358542821-phenyl-7H-pyrazolo[5,4-b]pyridin-6-one

Product 1

HCID 1358542805-Bromo-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-oneYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Bromine (76 μl, 1.47 mmol) was added to a solution of 1-phenyl-1,7-dihydropyrazolo[3,4-b]pyridin-6-one (0.31 g, 1.47 mmol) in acetic acid (7 ml) and the mixture was stirred for 30 min. The suspension was diluted with water, stirred for 10 min and then the precipitate filtered off, washing with water. The product was dried in a desiccator at 40° C. under vacuum for 17 h to give 5-bromo-1,7-dihydro-1-phenylpyrazolo[3,4-b]pyridin-6-one (0.29 g, 68%) as a brown solid. δH (400 MHz; DMSO) 7.32-7.37 (1H, m), 7.52-7.58 (2H, m), 8.12-8.24 (3H, m), 8.50 (1H, s); m/z (ES+) 290 (M+H+), 292 (M+H+).

Workup

  1. stirringstirred for 10 min
  2. filtrationthe precipitate filtered off
  3. washwashing with water
  4. customThe product was dried in a desiccator at 40° C. under vacuum for 17 h

Sources & evidence

ORD record
ord-952c512eebfc4b449c4344bdad50592d
Source dataset
uspto-grants-2003_04
Patent number
US06541484B2

Reaction notes

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