Dimethylformamide → HCID 67494898, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried Schlenk tube was flame-dried and backfilled with argon (3×). The tube was then charged with 6-chloro-4-ethoxy-3-(2-fluoro-4-(4-(trifluoromethoxy)phenoxy)phenyl)-7-methoxy-2-methylquinoline (0.3 g, 0.8 mmol), Pd(PPh3)4 (0.08 g, 10 mol %), and 2-fluoro-4-(4-(trifluoromethoxy)phenoxy)phenylboronic acid (0.375 g, 1.2 mmol). A rubber septum was then placed on the tube and 2M Na2CO3 (3 mL), DMF (15 mL), were added. The tube was then purged of air by argon for about 1 minute, while stirring and then heated at 90° C. until completion by HPLC analysis ˜3 h. After completion, reaction was boiled with 1:1 MeOH/CHCl3, and filtered over celite. The celite was then rinsed with boiling hot DMF. The filtrate was then evaporated on silica gel purified via flash chromatography (33% EtOAc in Hexane). The resulting amorphous solid (0.48 g, 52%) was then dissolved in 4.8 mL of AcOH and 4.8 mL of HBr. This solution was refluxed for 1.5 h. The reaction was poured onto ice and water. The resulting solid was filtered via filtration and recrystallized from DMF twice (0.2 g, 44%).

Provenance & Evidence