Potassium Carbonate → HCID 86684912, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence