2-Bromopyridine → HCID 66977380, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pivalamide (23.4 g, 72.97 mmol) in acetonitrile (280 mL) was added 2-bromopyridine (16.14 g, 102.12 mmol) and aqueous solution of K2CO3 (50.40 g, 364.90 mmol). The reaction mixture was degassed by purging N2 for 15 min followed by addition of tetrakis(triphenylphosphine)palladium(0) (8.40 g, 7.30 mmol). The mixture was again degassed for 10-15 min then heated up to 80° C. for 8 h. After completion of reaction (by TLC), the mixture was poured into 100 mL of ice-cold water and extracted with EtOAc (3×250 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 2.0% EtOAc:hexane to obtain the desired product as a colourless liquid (19.0 g, 96% yield).

Provenance & Evidence