Chlorosuccinimide → 2-(4-chloro-5-methyl-1H-pyrazol-3-yl)pyridine

HRID 1804827Notes

Reaction equation

HRID 1804827 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:3]=1.[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:3]1[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[N:5][NH:6][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 27555682-(5-methyl-1H-pyrazol-3-yl)pyridine

Product 1

HCID 578402932-(4-chloro-5-methyl-1H-pyrazol-3-yl)pyridineYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Preparation 2: A solution of 2-(5-methyl-1H-pyrazol-3-yl)pyridine (500 mg, 3.15 mmol) in acetonitrile (912 mL) was treated with N-chlorosuccinimide in 6 portions and the resulting mixture stirred at 70° C. for 14 h. The mixture was cooled and then concentrated in vacuo to yield a residue. The residue was partitioned between EtOAc (8 mL) and H2O (3 mL). The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to yield a residue. The residue was purified by flash chromatography on silica gel using 20-80% EtOAc in hexanes to give the title compound (300 mg, 53%).

Workup

  1. customPreparation 2
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customto yield a residue
  5. customThe residue was partitioned between EtOAc (8 mL) and H2O (3 mL)
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto yield a residue
  10. customThe residue was purified by flash chromatography on silica gel using 20-80% EtOAc in hexanes

Sources & evidence

ORD record
ord-2f746194448a418987a24597dc3e76c9
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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