Cesium carbonate → HCID 58188118, compound

Temperature

80 °C

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).

1. customThe resulting reaction mixture
2. customAfter completion of the reaction
3. temperaturethe reaction mixture was cooled to room temperature
4. extractionextracted with CH2Cl2
5. dry with materialThe organic layer was dried over anhydrous Na2SO4
6. customthe solvents were evaporated in vacuo
7. customThe residue was purified by column chromatography (SiO2, 5% Et2O/pentane)

ORD record

ord-f50d6c4d00384738bba4b19d79b6b6c3

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946439B2