Water → HCID 64428749, compound

HRID 906854Notes

Reaction equation

HRID 906854 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Cl[C:10]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][N:11]=1.O>CN(C)C=O>[I:3][C:4]1[CH:5]=[N:6][N:7]([C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 770224-IodopyrazoleHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 64428749HCID 64428749, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 243 mg, 6.07 mmol) was suspended in 4 mL anhydrous N,N-dimethylformamide. To this solution was added 4-iodo-1H-pyrazole (982 mg, 5.06 mmol) in 4 mL anhydrous N,N-dimethylformamide at 0° C. under nitrogen. The mixture was stirred at 0° C. for 15 min, and then allowed to warm to ambient temperature and stirred at the same temperature for 2 hrs. After this period of time, a solution of 2-chloro-3-trifluoromethyl-pyridine (1.01 g, 5.56 mmol) in 4 mL N,N-dimethylformamide was added and the mixture was heated at 90° C. for 5 hrs. After cooling off, the mixture was poured into water and extracted with ethyl acetate three times. The combined extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo to give 2-(4-iodo-pyrazol-1-yl)-3-trifluoromethyl-pyridine as a white solid (1.406 g, 74% yield). The product was used for the next step without purification. 1H-NMR (400 MHz, CDCl3): δ 7.48 (dd, 1H, J=4.80, J=8.08), 7.79 (s, 1H), 8.21 (dd, 1H, J=1.52, J=8.08), 8.27 (s, 1H), 8.67 (dd, 1H, J=1.52, J=4.80).

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred at the same temperature for 2 hrs
  3. waitAfter this period of time
  4. temperaturethe mixture was heated at 90° C. for 5 hrs
  5. temperatureAfter cooling off
  6. extractionextracted with ethyl acetate three times
  7. extractionThe combined extract
  8. washwas washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1e03b96a9a847e286ef5a09503d7126
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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