Triethylamine → HCID 59475105, compound

Participants

Reaction Conditions

Reaction Steps

In a sulfonation flask a mixture containing of 240 mg (0.58 mmol) 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid[2-(5-bromo-3-chlorothiophen-2-yl)-1-methylethyl]amide, 80 mg (1.15 mmol) cyclopropyacetylene, 10 mg copper(I)iodide, 36 mg (0.05 mmol) bistriphenylphosphine palladium dichloride and 30 ml triethylamine is stirred at 60° C. for 2 days. Then another 80 mg of cyclopropylacetylene is added and stirring continued for 24 hours. After cooling to ambient temperature ethylacetate and water is added and the organic layer separated and washed again twice with water. After drying (sodium sulphate) and distilling off the solvent in a water jet vacuum, the crude product is obtained. Purification is achieved by column chromatography over silicagel (eluent: ethylacetate/heptane 1:1). Yield: 90 mg (23% of theory) of a slightly brown resin (1H-NMR: 0.8/m/2H, 0.9/m/2H, 1.22/d/3H, 1.45/m/1H, 3.01/d/2H, 3.9/s/3H, 4.40/m/1H, 6.28/s (broad)/1H, 6.88/t/1H—CF2H, 6.89/s/1H, 7.85/s/1H).

Provenance & Evidence