Sodium Carbonate → HCID 57438770, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine, (Example #F.1.34, 0.25 g, 0.27 mmol), tris(dibenylideneacetone)dipalladium(0) (0.0306 g, 0.034 mmol), sodium carbonate (0.213 g, 2.0 mmol), and tri-t-butylphosphine tetrafluoroborate (Strem, 0.0194 g, 0.07 mmol) were combined in water (0.645 mL) and dioxane (3.35 mL). The reaction was degassed with nitrogen and vinylboronic acid pinacol ester (0.227 mL, 1.34 mmol) was added and the reaction heated at about 95° C. overnight. The reaction was poured onto a pad of silica gel and eluted with EtOAc. The EtOAc solution was washed with brine, dried over sodium sulfate, and concentrated. Ethanol (7.5 mL), EtOAc (7.5 mL), and 10% palladium on carbon (0.050 g) were added. The reaction was purged with hydrogen and stirred under a balloon of hydrogen for about 4 h. The reaction was filtered and concentrated. The residue was purified by FCC using 1:1 EtOAc/heptane and then triturated with heptane to provide the title compound (0.16 g, 65%) on drying: LC/MS (Table 1, Method b) Rt=2.52 min; MS m/z: 366.3 (M+H)+.

Provenance & Evidence