Triethylamine → 2-(3-Chlorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine

HRID 354253Notes

Reaction equation

HRID 354253 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:20]O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.CS(Cl)(=O)=O.C(N(CC)CC)C>COCCOC>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]3[N:20]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86590215HCID 86590215, compound

Product 1

HCID 99440482-(3-Chlorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridineYield 91.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

To a suspension of 1-(3-chlorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone oxime (17 g, 54 mmol) in DME (170 ml) at −5° C. was added dropwise methanesulfonyl chloride (4.5 m, 6.0 mmol) and the mixture stirred for 15 mins. Triethylamine (16.5 ml, 120 mmol) in DME (7 ml) was then added dropwise over 15 min. After the addition was complete, the mixture was then warmed to 35° C. for 45 minutes. This was then cooled and filtered, washing with DME (20 ml). To the filtrate was added iron (II) chloride (75 mg) and the mixture heated to 70° C. for 1 hour and then allowed to cool. The reaction was concentrated to half the original volume and water (100 ml) was added. The resulting solid was removed by filtration, washed with water and dried. The solid was dissolved in ethyl acetate and washed with water and brine and then dried over magnesium sulfate. Filtering and evaporation to dryness under vacuum afforded 14.6 g (91%) of the title compound.

Workup

  1. additionAfter the addition
  2. temperatureThis was then cooled
  3. filtrationfiltered
  4. washwashing with DME (20 ml)
  5. additionTo the filtrate was added iron (II) chloride (75 mg)
  6. temperaturethe mixture heated to 70° C. for 1 hour
  7. temperatureto cool
  8. concentrationThe reaction was concentrated to half the original volume and water (100 ml)
  9. additionwas added
  10. customThe resulting solid was removed by filtration
  11. washwashed with water
  12. customdried
  13. dissolutionThe solid was dissolved in ethyl acetate
  14. washwashed with water and brine
  15. dry with materialdried over magnesium sulfate
  16. filtrationFiltering
  17. customevaporation to dryness under vacuum

Sources & evidence

ORD record
ord-6adf5b0b5a6146cf8921746adc5c2ce5
Source dataset
uspto-grants-2004_06
Patent number
US06756498B2

Reaction notes

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