Réaction #2028892

ord-6f1cf560ed8e450d9d3713ae1c50e0ce

Équation de réaction

NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(CBr)c2-c2ccccc2)cc1
compound
NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(CBr)c2-c2ccccc2)cc1
4-[4-bromomethyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
Cc1cc(C)nc(C)c1
collidine
CS(C)=O
dimethyl sulfoxide
NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(C=O)c2-c2ccccc2)cc1
desired product
Rendement 66.0%
NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(C=O)c2-c2ccccc2)cc1
4-[4-formyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
Rendement 66.0%

Conditions de réaction

Température
120°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe reaction solution was partitioned between ethyl acetate and water
  2. 2
    Lavagethe organic solution was washed with water
  3. 3
    Autredried
  4. 4
    Concentrationconcentrated
  5. 5
    AutreThe residue was chromatographed (1:1 hexane:ethyl acetate)

Mode opératoire

To a solution of the compound prepared in Step 1 (362 mg, 0.79 mmol) in dimethyl sulfoxide (7 mL) was added collidine (0.14 mL, 1.0 mmol). The solution was heated at 120° C. for 3 hours and then kept at overnight at room temperature. The reaction solution was partitioned between ethyl acetate and water and the organic solution was washed with water, dried and concentrated. The residue was chromatographed (1:1 hexane:ethyl acetate) to give the desired product (205 mg, 66%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE044048E1uspto-grants-2013_03