A solution of 3-bromo-2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine (0.25 g, 0.9 mmol) and p-fluorophenyl-boronic acid (0.15 g, 1.04 mmol), in DME (10 mL) is purged with argon. The solution is treated with NaOH (0.07 g, 1.7 mmol) and (PPh3)4Pd (0.05 g, 0.04 mmol) then heated at reflux overnight. The reaction is then cooled, diluted in EtOAc, and washed with water and brine. The organic solution is dried over MgSO4 and the solvent removed in vacuo. The residue is purified by silica gel column chromatography using a mixture of hexanes/EtOAc to afford 0.164 g (62%) of desired product as a white solid. UV (95% EtOH) λmax 248 nm (ε 20386). TOF MS ES+ exact mass calculated for C19H14FN3 (p+1): m/z=304.1250. Found: 304.1249. Anal. Calcd for C19H14FN3: C, 75.23; H, 4.65; N, 13.85. Found: C, 75.10; H, 4.76; N, 13.70.
