Sodium Carbonate → HCID 69082787, compound

Participants

Reaction Steps

To a 15 mL round bottom flask was added 5-bromo-2-fluoropyridin-3-ylboronic acid (895 mg, 4.07 mmol), sodium carbonate (863 mg, 8.14 mmol) and 1-fluoro-4-vinylbenzene (647 mg, 5.29 mmol) in dimethylformamide (8 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 (91 mg, 0.407 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. The next day 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 purified by silica gel chromatography eluting with 0% EtOAc/100% hexanes to 15% EtOAc/85% hexanes affording (E)-5-bromo-2-fluoro-3-(4-fluorostyryl)pyridine (380 mg, 1.283 mmol, 31.5% yield) as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 8.15 (s, 1H), 8.09 (dd, J=8.0, 2.0, 1H), 7.55-7.52 (m, 2H), 7.22 (d, J=16.0, 1H), 7.13-7.09 (m, 2H), 7.00 (d, J=16.0, 1H), LC/Mass spec. (Analytical HPLC method 2): RT=2.31 min. Mass=296.08 (MH)+.

Provenance & Evidence