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-(4-methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (84 mg, 0.27 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=1:1) to afford the desired product (61 mg, quant) as a yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.79 (d, J=2.3 Hz, 1H), 8.17 (dd, J=7.4 Hz and 1.7 Hz, 1H), 8.06-8.00 (m, 2H), 7.95 (d, J=8.6 Hz, 2H), 7.63 (d, J=8.6 Hz, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.32 (td, J=7.4 Hz and 1.7 Hz, 1H), 7.20 (d, J=8.0 Hz, 1H), 7.17 (td, J=8.0 Hz and 1.7 Hz, 1H), 7.00-6.95 (m, 3H), 6.83-6.78 (m, 1H), 6.61 (dd, J=8.0 Hz and 4.6 Hz, 1H), 6.26 (s, 1H), 5.12 (br s, 1H), 3.86 (s, 3H), 2.58-2.42 (m, 4H), 2.18-2.11 (m, 1H), 1.94-1.87 (m, 1H), 1.40 (br s, 9H). LCMS: 663 [M+H].
