Bromine → 4-(4-bromo-1H-pyrazol-1-yl)pyridine

HRID 2274761Notes

Reaction equation

HRID 2274761 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[Br:12]Br>C(O)(=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:12][C:4]1[CH:3]=[N:2][N:1]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 200417044-(1H-Pyrazol-1-yl)pyridine2×

Product 1

HCID 545954894-(4-bromo-1H-pyrazol-1-yl)pyridineYield 55%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of 4-(1H-pyrazol-1-yl)pyridine (Intermediate 7; 1.1 g; 7.5 mmol) in acetic acid (10 mL) was added a solution of bromine (6 mL) in acetic acid (10 mL) dropwise. The reaction mixture was stirred for 4 hours, diluted with saturated aqueous Na2S2O3 (20 mL), and extracted with DCM (10 mL×3). The combined organic layers were washed with saturated aqueous NaHCO3 (20 mL), water (20 mL), brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated to afford 936 mg (55%) of the title compound as a pink solid.

Workup

  1. extractionextracted with DCM (10 mL×3)
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3 (20 mL), water (20 mL), brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-17a3d2aa27e4443195c3eaf9e5d7dde5
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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