3-(Biphenyl-2-ylmethyl)-5,7-dichloro-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one (0.192 g, 0.469 mmol), N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pivalamide (0.214 g, 0.703 mmol, 1.2 eq), Palladium (II) acetate (0.2 eq), triphenyl phosphine (0.2 eq) and cesium carbonate (2 eq) were heated at 100° C. in DMF (3 mL) under an atmosphere of nitrogen in a sealed tube for 1.5 h. The mixture was cooled then diluted with ethyl acetate and water (2:1) then filtered through a pad of celite. The layers were separated and the organic phase was washed with brine then dried over sodium sulfate. Chromatography eluting with 1:1 ethyl acetate in hexanes gave an oil which was dissolved in a 2:1 mixture of acetonitrile and water and freeze-dried to give product as an off-white solid (0.096 g, 37% yield). 1H-NMR (300 MHz, CDCl3) δ 8.29-8.22 (m, 2H), 8.09 (s, 1H), 7.71 (dd, 1H), 7.51-7.47 (m, 2H), 7.32-7.28 (m, 2H), 7.20-7.12 (m, 8H), 3.69-3.55 (m, 2H), 3.41-3.36 (m, 1H), 3.31 (s, 3H), 1.33 (s, 9H). MS (APCI) m/z 551 (M+1).
