Propargyl bromide → HCID 19025378, compound

Participants

Reaction Steps

These compounds were prepared in a manner analogous to that of Step I of Example 1, using 1.0 gram (0.002 mole) of 3-(6-fluoro-3-trifluoromethylquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil, 0.7 gram (0.005 mole) of 80% 3-bromopropyne, and 0.7 gram (0.005 mole) of potassium carbonate in 40 mL of N,N-dimethylformamide. The crude reaction product was subjected to column chromatography on silica gel. Elution was accomplished using 1:4 ethyl acetate-hexane and 1:1 ethyl acetatehexane. The appropriate product-containing fractions were combined and concentrated under reduced pressure, yielding 0.8 gram of 3-[1-(2-propyn-1-yl)-3-trifluoromethyl-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 42), mp 248°-250° C. Other product-containing fractions were combined and concentrated under reduced pressure, yielding 0.1 gram of the O-alkylated product, 3-[2-(2-propyn-1-yloxy)-3-trifluoromethyl-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 26A). The NMR spectra were consistent with the proposed structures.

Provenance & Evidence