Sodium Carbonate → HCID 68067214, compound

Participants

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 (30 mg, 0.058 mmol), m-acetylphenyl boronic acid (19 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 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=1:1×2) to afford the desired product (27 mg, 77%) as a yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.17 (dd, J=7.7, 1.4 Hz, 1H), 8.02 (d, J=4.6 Hz, 1H), 7.86 (d, J=8.6 Hz, 2H), 7.68 (d, J=8.6 Hz, 2H), 7.40 (d, J=8.0 Hz, 2H), 7.32 (td, J=8.0, 1.7 Hz, 1H), 7.18-7.15 (m, 2H), 6.96 (d, J=8.0 Hz, 1H), 6.80 (d, J=7.4 Hz, 1H), 6.60 (dd, J=8.0, 5.2 Hz, 1H), 6.25 (s, 1H), 5.13 (br s, 2H), 2.59-2.53 (m, 5H), 2.50-2.42 (m, 2H), 2.21-2.12 (m, 1H), 1.95-1.87 (m, 1H), 1.40 (br s, 9H). LCMS: 598 [M+H].

Provenance & Evidence