Potassium Carbonate → HCID 86684912, compound

Temperature

88 °C

To a stirred suspension of 4-fluoro-3-(trifluoromethyl)phenylboronic acid (42.6 g, 205 mmol) in toluene (200 mL) were added 4-bromo-2-methylpyridine (34.4 g, 200 mmol) and 2 M aqueous potassium carbonate (200 mL). After the addition of 1,1′-bis(diphenylphosphino)-ferrocene-palladium(II)dichloride dichloromethane complex (81.7 mg, 0.1 mmol), the two-phase, yellowish reaction mixture was stirred under reflux at 88° C. for 23 h. The resultant brownish reaction mixture was cooled to room temperature and extracted with toluene (200 mL). After washing with 10% brine (200 mL), the toluene layer was dried with Na2SO4 (50 g) and then treated under stirring with charcoal (2 g) for 30 min. Filtration and evaporation (50° C./≧10 mbar) afforded the crude title product (50.7 g, 99.4%) as an off-white, crystalline residue which was used without purification in the next step. 1H NMR (CDCl3, 400 MHz) δ 2.64 (s, 3H), 7.25-7.36 (m, 3H), 7.76-7.82 (m, 1H), 7.84 (dd, J1=6.7 Hz, J2=2.4 Hz, 1H), 8.58 (d, J=5.0 Hz, 1H). ESI-MS (m/z) [M+H]+256.3 (100).

1. additionAfter the addition of 1,1′-bis(diphenylphosphino)-ferrocene-palladium(II)dichloride dichloromethane complex (81.7 mg, 0.1 mmol)
2. customthe two-phase, yellowish reaction mixture
3. customThe resultant brownish reaction mixture
4. temperaturewas cooled to room temperature
5. extractionextracted with toluene (200 mL)
6. washAfter washing with 10% brine (200 mL)
7. dry with materialthe toluene layer was dried with Na2SO4 (50 g)
8. additiontreated
9. stirringunder stirring with charcoal (2 g) for 30 min
10. filtrationFiltration and evaporation (50° C./≧10 mbar)

ORD record

ord-8dcfa69fd251473ebba118102e21298a

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796471B2