Cesium carbonate → HCID 58188118, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of potassium vinyltrifluoroborate (3.32 g, 24.8 mmol), PdCl2 (0.1 g, 0.56 mmol) and PPh3 (0.45 g, 1.71 mmol) in 60 mL of THF—H2O (9:1) were added Cs2CO3 (20.2 g, 62 mmol) and 5-bromo-2-(difluoromethyl)pyridine (4.3 g, 20.7 mmol). The resulting reaction mixture was heated to 80° C. and stirred for 16 h. After completion of the reaction, the reaction mixture was cooled to room temperature, treated with water and extracted with CH2Cl2. The organic layer was dried over anhydrous Na2SO4 and the solvents were evaporated in vacuo. The residue was purified by column chromatography (SiO2, 5% Et2O/pentane) to afford the title compound (2.46 g, 75% yield). MS: 156 [M+1]+; 1H-NMR (300 MHz, CDCl3): δ 8.64 (s, 1H), 7.86 (d, 1H, J=8.3 Hz), 7.60 (d, 1H, J=8.3 Hz), 6.74 (dd, 1H, J=18, 11.2 Hz), 6.63 (t, 1H, J=55.6 Hz), 5.91 (d, 1H, J=18 Hz), 5.48 (d, 1H, J=11.2 Hz).

Provenance & Evidence