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), 2-quinolin-6-ylboronic acid (31 mg, 0.18 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=1:4) to afford the desired product (53 mg, 98%) as a pale yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.85 (dd, J=4.0 Hz and 1.7 Hz, 1H), 8.22 (dd, J=8.0 Hz and 1.7 Hz, 1H), 8.19-8.14 (m, 1H), 8.08 (d, J=7.4 Hz, 1H), 8.03 (d, J=3.4 Hz, 1H), 7.94-7.92 (m, 1H), 7.87-7.79 (m, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.36-7.31 (m, 2H), 7.21-7.17 (m, 3H), 6.97 (d, J=7.4 Hz, 1H), 6.84 (d, J=7.4 Hz, 1H), 6.62 (dd, J=8.0 Hz and 4.6 Hz, 1H), 6.29 (s, 1H), 5.15 (br s, 1H), 2.58-2.53 (m, 2H), 2.50-2.40 (m, 2H), 2.20-2.12 (m, 1H), 1.95-1.87 (m, 1H), 1.40 (br s, 9H). LCMS: 607 [M+H].
