Reaction Steps
A mixture of tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.097 mmol), 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]morpholine (59 mg, 0.20 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (7 mg, 0.1 mmol), and 2M Na2CO3 aq. (0.097 mL, 0.20 mmol) in DMF (1.5 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 twice by preparative thin-layer chromatography (CH2Cl2/MeOH=10:1×2) and (AcOEt/MeOH=10:1) to afford the desired product (28 mg, 44%) as a yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.17 (dd, J=8.0 Hz and 1.7 Hz, 1H), 8.00 (d, J=4.6 Hz, 1H), 7.54 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 7.30 (td, J=8.0 Hz and 1.7 Hz, 1H), 7.22 (d, J=8.0 Hz, 1H), 7.17-7.13 (m, 3H), 6.94 (d, J=8.0 Hz, 1H), 6.80 (d, J=6.9 Hz, 1H), 6.59 (dd, J=8.0 Hz and 5.2 Hz, 1H), 6.24 (s, 1H), 5.10 (br s, 1H), 3.70 (t, J=4.6 Hz, 4H), 3.47 (s, 2H), 2.57-2.50 (m, 2H), 2.45-2.42 (m, 4H), 2.19-2.10 (m, 2H), 1.93-1.85 (m, 2H), 1.39 (br s, 9H). LCMS: 655 [M+H].
