Pyrazole → 5-Bromo-2-(1H-pyrazol-1-yl)pyridine

HRID 1166096Notes

Reaction equation

HRID 1166096 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].Br[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1>CN(C=O)C>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 226311445-Bromo-2-(1H-pyrazol-1-yl)pyridineYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyrazole (2.05 g, 30.11 mol) was added in portions to sodium hydride (60% in oil, 1.20 g, 30.00 mmol) in DMF (40 mL) and the resulting mixture was stirred for 1 h at RT. 2,5-Dibromopyridine (4.75 g, 20.05 mmol) was added and the mixture was heated to 100° C. for 2 h. Ice-water (100 mL) was added to the cooled reaction mixture and the precipitated solids were removed by filtration and allowed to air-dry. Recrystallization from hexane provided 3.31 g (74%) of the title compound as a tan solid. MS 224 (M+H)+.

Workup

  1. temperaturethe mixture was heated to 100° C. for 2 h
  2. customthe precipitated solids were removed by filtration
  3. customto air-dry
  4. customRecrystallization from hexane

Sources & evidence

ORD record
ord-d42a361bbd204cae93b28e0687e6bc81
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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