Sodium Carbonate → Methyl 4-[3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl]benzoate

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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 (30 mg, 0.058 mmol), [4-(methoxy carbonyl)phenyl]boronic acid (21 mg, 0.12 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (4 mg, 0.006 mmol), and 2M Na2CO3 aq. (0.058 mL, 0.12 mmol) in DMF (1 mL) was heated in microwave oven at 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 (28 mg, 78%) as a white solid. 1HNMR (CDCl3) 400 MHz δ: 8.17 (dd, J=8.0 Hz and 1.7 Hz, 1H), 8.02 (d, J=4.0 Hz, 1H), 7.93 (d, J=8.6 Hz, 2H), 7.65 (d, J=8.0 Hz, 2H), 7.38 (d, J=8.0 Hz, 2H), 7.32 (td, J=7.4, 1.1 Hz, 1H), 7.18-7.15 (m, 2H), 6.95 (d, J=8.0 Hz, 1H), 6.80 (d, J=7.4 Hz, 1H), 6.60 (dd, J=8.0 Hz and 4.6 Hz, 1H), 6.25 (s, 1H), 5.13 (br s, 1H), 3.90 (s, 3H), 2.58-2.41 (m, 4H), 2.20-2.11 (m, 1H), 1.95-1.87 (m, 1H), 1.40 (br s, 9H). LCMS: 614 [M+H].

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