Triethylamine → 2-Cyano-4-[1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

HRID 1635503Notes

Reaction equation

HRID 1635503 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][N:22]=1)[CH2:13][C:14](=O)[CH2:15][C:16](=O)C)#[N:9].Cl.[F:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1>C(O)C>[C:8]([C:10]1[CH:11]=[C:12]([C:13]2[N:31]([C:28]3[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=3)[N:32]=[C:15]([CH3:16])[CH:14]=2)[CH:20]=[CH:21][N:22]=1)#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 544384121-(2-Cyanoisonicotinyl)-1,3-butanedione

Product 1

HCID 186761072-Cyano-4-[1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]pyridineYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (4.6 mL, 0.033 mol) was added dropwise to a mixture of 1-(2-cyanoisonicotinyl)-1,3-butanedione (6.0 g, 0.032 mol) and 4-fluorophenylhydrazine hydrochloride (5.37 g, 0.033 mol) in 100 mL of ethanol. The reaction mixture was heated at reflux overnight (about eighteen hours). The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by recrystallization from ether/hexane to give 4.7 g (53% yield) of product as a yellow solid: mp: 94-95° C.; Anal. Calc'd. for C16H11FN4: C, 69.06; H, 3.98; N, 20.13. Found: C, 68.52; H, 3.89; N, 19.73.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight (about eighteen hours)
  3. customThe solvent was removed
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by recrystallization from ether/hexane

Sources & evidence

ORD record
ord-3fb7bd549adb44e5af4125f1c000b86a
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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