Sodium Carbonate → HCID 69083492, compound

Participants

Reaction Steps

To a 15 mL round bottom flask was added 5-bromo-2-fluoropyridin-3-ylboronic acid (400 mg, 1.820 mmol), SODIUM CARBONATE (386 mg, 3.64 mmol) and 1-(trifluoromethyl)-4-vinylbenzene (407 mg, 2.366 mmol) in dimethylformamide (6 mL). The solution was stirred at room temperature and the flask was purged with oxygen for 3 min. To the purged flask was quickly added palladium(II) acetate (40.9 mg, 0.182 mmol) and the reaction flask was again sealed and purged with oxygen for 15 min. The reaction mixture was then stirred at room temperature overnight and monitored by TLC to determine when the reaction was complete. The next day the reaction was complete by LC/MS. There was no boronic acid left so the reaction was quenched with water and diluted with ethylacetate. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated in vacuo. The crude oil was puried by silica gel chromatography eluting with 0% EtOAc/100% hexanes to 15% EtOAc/85% hexanes affording (E)-5-bromo-2-fluoro-3-(4-(trifluoromethyl)styryl)pyridine (177 mg, 0.511 mmol, 28.1% yield) as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 8.19 (s, 1H), 8.12 (dd, J=8.0, 4.0, 1H), 7.66 (m, 4H), 7.29 (d, J=16.0, 1H), 7.17 (d, J=16.0, 1H).

Provenance & Evidence