Ethyl Acetate → 3-(4-bromo-1H-pyrazol-1-yl)pyridine

HRID 2359914Notes

Reaction equation

HRID 2359914 reaction equation
[N:1]1([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[Br:34]N1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C>[Br:34][C:4]1[CH:3]=[N:2][N:1]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 9869224Ammonium cerium (IV) nitrateHCID 113785673-(1H-pyrazol-1-yl)pyridine

Product 1

HCID 126612093-(4-bromo-1H-pyrazol-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Pyrazol-1-ylpyridine (500 mg, 3.44 mmol) was dissolved in acetonitrile (15 ml), and ammonium cerium(IV) nitrate (944 mg, 1.72 mmol) was added (slightly exothermic). N-Bromosuccinimide (736 mg, 4.13 mmol) was added in portions (slightly exothermic) and the mixture was stirred at room temperature for 30 minutes (min) and then heated under reflux for 3 hours (h). After the mixture had cooled, ethyl acetate was added. The organic phase was washed with water, washed with a sodium sulphate solution and then dried over magnesium sulphate. The solvent was removed on a rotary evaporator under reduced pressure.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours (h)
  3. temperatureAfter the mixture had cooled
  4. washThe organic phase was washed with water
  5. washwashed with a sodium sulphate solution
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed on a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-301b39ec8fc0492ea3693caf5617d22d
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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