Methyl vinyl ketone → HCID 178467735, compound

Participants

Reaction Steps

A solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example No. 5 (1.0 g), Pd(OAc)2 (9 mg), P(o-tolyl)3 (45.7 mg), methyl vinyl ketone (0.23 mL), and Et3N (0.78 mL) in 5.28 mL anhydrous DMF is heated in a sealed tube at 100° C. overnight. The reaction mixture is cooled to room temperature and then cooled in an ice bath. The cooled reaction mixture is poured into 20 mL ice cold 1N HCl. A brown solid precipitated and is collected. The crude product is adsorbed onto silica and chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 453.4 mg (52%) of the title compound as a yellow solid.

Provenance & Evidence