Water → HCID 178516986, compound

HRID 1017631Notes

Reaction equation

HRID 1017631 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]2=[N:15][C:16]([OH:19])=[CH:17][CH:18]=[C:13]2[N:12]=[N:11]1.O>C(O)(=O)C>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]2=[N:15][C:16]([OH:19])=[C:17]([Br:1])[CH:18]=[C:13]2[N:12]=[N:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 178515799HCID 178515799, compound

Product 1

HCID 178516986HCID 178516986, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.10 ml, 2 mmol) was added to a stirred solution of 3-(2-fluorophenyl)-5-hydroxy-1,2,3-triazolo[4,5-b]pyridine (0.23 g, 1.0 mmol) in glacial acetic acid (5 ml) at room temperature. After 4 h the solution was poured into water (150 ml). The precipitate was collected, dissolved in 10% methanol-dichloromethane (100 ml), dried (Na2SO4), filtered and concentrated to give 3-(2-fluorophenyl)-5-hydroxy-6-bromo-1,2,3-triazolo[4,5-b]pyridine (0.282 g, 91%) as a beige solid. δH (360 MHz; CDCl3) 7.42-7.47 (2H, m), 7.60-7.71 (2H, m) and 8.48 (1H, s); m/z (ES+) 309, 311 (M+H+).

Workup

  1. customThe precipitate was collected
  2. dissolutiondissolved in 10% methanol-dichloromethane (100 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6fd1dbd0336747c7895cca6759c96932
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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