To a suspension of 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9) in 1-propanol (0.1 M) was added [(E)-2-(4-fluorophenyl)vinyl]boronic acid (1.5 equiv), 2.0 M aqueous Na2CO3 solution (2.5 equiv), and a 3:1 mixture of Ph3P:Pd(OAc)2 (0.1 equiv). The mixture was degassed and then stirred at 100° C. for 2.5 h, and was then partitioned between EtOAc/THF and H2O. The organic layer was washed with H2O and brine, and was then dried (MgSO4), filtered, and evaporated. The crude material was purified by flash chromatography, eluting with 1:1 Et2O:hexanes. The product was stirred with 1:10 EtOAc:hexanes containing trace acetone to yield the title compound as a pale yellow solid after filtration.
