Reaction #2056623

Reaction equation

ethyl 5-fluoro-1-[4-(4-iodo-1H-pyrazol-1-yl)benzyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate

potassium vinyltrifluoroborate

cesium carbonate

→

title compound

Ethyl 5-fluoro-4-oxo-1-[4-(4-vinyl-1H-pyrazol-1-yl)benzyl]-1,4-dihydroquinoline-3-carboxylate

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Concentrationconcentrated in vacuo

Procedure

To a solution of ethyl 5-fluoro-1-[4-(4-iodo-1H-pyrazol-1-yl)benzyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.080 g, 0.15 mmol), potassium vinyltrifluoroborate (0.013 g, 0.19 mmol), and 1 N cesium carbonate (0.31 mL, 0.31 mmol) in 2 mL of acetonitrile under nitrogen was added bis(tri-tert-butylphosphoranyl)palladium (10 mol %). The reaction mixture was stirred at 100° C. for 14 hours, cooled to room temperature, and concentrated in vacuo to provide the title compound (crude) which gave a mass ion (ES+) of 417.9 for M+H+. This compound could be further hydrolyzed to the corresponding carboxylic acid, as described in Example 1.

Source