A solution of N-(5-bromothiazolo[5,4-b]pyridin-2-yl)benzamide (reagent preparation 13) (0.14 g, 0.42 mmol), (4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)boronic acid (0.14 g, 0.35 mmol) and diisopropyethylamine (0.40 mL, 2.10 mmol) in 10% aqueous dimethylformamide (3 mL) was deoxygenated for five minutes by bubbling nitrogen gas, followed by the addition of 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) complex with dichloromethane (20 mg, 0.021 mmol). The reaction mixture was heated to 105° C. for 4 hours. On cooling to room temperature the mixture was diluted with ethyl acetate (50 mL) then it was filtered through a pad of Celite. The organic filtrate was washed with 10% aqueous citric acid (20 mL), brine, aqueous saturated sodium bicarbonate (20 mL) and brine then dried over anhydrous sodium sulfate, filtered and concentrated. Silica gel chromatography (chloroform/methanol 95:5 to 9:1) provided N-[5-(4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl]benzamide (86 mg. 41%). MS (EI) for C34H27FN6O2S: 603 (MH+).
