Potassium Carbonate → N-[4-Chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-ethenyl-1H-pyrazol-5-carboxamide

Participants

Reaction Steps

In succession, 18.5 mg (0.016 mmol) of tetrakis(triphenylphosphine)palladium, 0.044 g (0.320 mmol) of potassium carbonate in 1 ml of water, and 0.077 g (320 μmol of 2,4,6-trivinylcyclotriboroxane pyridine complex are added to a solution of 180 mg (0.32 mmol) of N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-iodo-1H-pyrazole-5-carboxamide from Example Ik-4 in 3 ml of dimethoxyethane, and the reaction mixture is heated under reflux for 20 hours. The solvent is completely distilled off at reduced pressure on a rotary evaporator and the residue is purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate; gradient: 2 hours, from 0% to 100% ethyl acetate). This gives 0.107 g of N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-ethenyl-1H-pyrazole-5-carboxamide (70%) as an oil.

Provenance & Evidence