Reaction Steps
A mixture of tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.090 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-benzofuran-1(3H)-one (80 mg, ca.0.267 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (6 mg, 0.09 mmol), and 2M Na2CO3 aq. (0.090 mL, 0.18 mmol) in DMF (2.5 mL) was treated with microwave (160° C. for 1 hour). The mixture was diluted with AcOEt, washed with water(×3), brine, dried over Na2SO4, then filtrated through Celite pad. The filtrate was concentrated and the residue was purified by preparative thin-layer chromatography (n-hexane/AcOEt=1:2) to afford the desired product (39 mg, 71%) as a white solid. 1HNMR (CDCl3) 400 MHz δ: 8.15 (dd, J=8.0 Hz and 1.7 Hz, 1H), 8.03 (d, J=4.0 Hz, 1H), 7.87-7.83 (m, 2H), 7.74-7.72 (m, 1H), 7.65-7.59 (m, 2H), 7.41 (d, J=8.6 Hz, 1H), 7.34 (td, J=7.4 Hz and 1.7 Hz, 1H), 7.19-7.16 (m, 2H), 6.97 (d, J=7.4 Hz, 1H), 6.80 (d, J=7.4 Hz, 1H), 6.61 (dd, J=8.0 Hz and 4.6 Hz, 1H), 6.26 (s, 1H), 5.27 (s, 2H), 5.15 (br s, 1H), 2.59-2.52 (m, 2H), 2.50-2.40 (m, 2H), 2.21-2.12 (m, 1H), 1.96-1.87 (m, 1H), 1.39 (br s, 9H). LCMS: 612 [M+H].
