Hydrochloric Acid → HCID 178510923, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example 5 (0.76 g), Pd(OAc)2 (0.0070 g), P(o-tolyl)3 (0.033 g), acrylonitrile (0.14 mL), NEt3 (0.59 mL), and DMF (4 mL). The tube was capped tightly and heated at 100° C. overnight behind a blast shield. The reaction was cooled to room temperature and poured into 20 mL 1N HCl. The resulting solid was filtered, dissolved in hot EtOH, and adsorbed onto silica. Chromatography on a Biotage Flash 40S column (eluent 1.5% MeOH:CH2Cl2 (2 L) followed by 2.5% MeOH:CH2Cl2 (1 L) and 3% MeOH:CH2Cl2 (1 L)) afforded the desired product as a tan solid (0.47 g, 74%).

Provenance & Evidence