p-Fluoronitrobenzene → 1-(4-Nitrophenyl)-3-(3-pyridinyl)-5-ethylpyrazole

HRID 1634126Notes

Reaction equation

HRID 1634126 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:11]=[C:10]([CH2:12][CH3:13])[NH:9][N:8]=2)[CH:2]=1.CC([O-])(C)C.[K+].F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1>CS(C)=O>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([N:9]2[C:10]([CH2:12][CH3:13])=[CH:11][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:8]2)=[CH:22][CH:23]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 158808993-(5-Ethyl-1H-pyrazol-3-YL)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 158808931-(4-Nitrophenyl)-3-(3-pyridinyl)-5-ethylpyrazoleYield 83.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(3-pyridinyl)-5-ethylpyrazole (13.2 g, 75.6 mmol) in DMSO (70 mL) was added t-BuOK (9.3 g, 83.2 mmol), and then 4-fluoronitrobenzene (8.8 mL, 83.2 mmol). The mixture was heated to 80° C. for 1 hr. After being cooled to room temperature, the mixture was quenched with water (300 mL). The resulting slurry was stirred for 30 min and filtered. The cake was washed with water and dried in oven under house vacuum at 40° C. overnight. The solid was then treated with a 1:2 mixture of ethyl acetate and hexane (150 mL) and the slurry was filtered. The solid was washed with the same solvent system and dried in an oven under house vacuum to give 1-(4-nitrophenyl)-3-(3-pyridinyl)-5-ethylpyrazole (18.5 g, 82%). 1H NMR (CDCl3, 400 MHz) 9.09 (s, 1H), 8.60 (d, J=4.0 Hz, 1H), 8.38, 7.76 (ABq, J=9.04 Hz, 4H), 8.17(m, 1H), 7.36 (m, 1H), 6.67 (s, 1H), 2.84 (q, J=7.5Hz, 2H), 1.36 (t, J=7.5 Hz, 3H).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customthe mixture was quenched with water (300 mL)
  3. filtrationfiltered
  4. washThe cake was washed with water
  5. customdried in oven under house vacuum at 40° C. overnight
  6. additionThe solid was then treated with a 1:2 mixture of ethyl acetate and hexane (150 mL)
  7. filtrationthe slurry was filtered
  8. washThe solid was washed with the same solvent system
  9. customdried in an oven under house vacuum

Sources & evidence

ORD record
ord-e65c6e7a09d34485a0f9d980e94f9209
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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