Sodium Carbonate → HCID 68084994, 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 (50 mg, 0.097 mmol), [4-(hydroxymethyl)phenyl]boronic acid (30 mg, 0.20 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (7 mg, 0.01 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 by preparative thin-layer chromatography (n-hexane/AcOEt=1:2) to afford the desired product (15 mg, 26%) as a pale yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.17 (dd, J=8.0 Hz and 1.1 Hz, 1H), 8.01 (d, J=4.0 Hz, 1H), 7.58 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 7.31 (td, J=7.4 Hz and 1.7 Hz, 1H), 7.28-7.24 (m, 2H), 7.16-7.13 (m, 3H), 6.95 (d, J=7.4 Hz, 1H), 6.80 (d, J=7.4 Hz, 1H), 6.60 (dd, J=8.0 Hz and 5.2 Hz, 1H), 6.24 (s, 1H), 5.11 (br s, 1H), 4.68 (d, J=5.7 Hz, 2H), 3.49 (d, J=5.7 Hz, 1H), 2.57-2.51 (m, 4H), 2.19-2.10 (m, 1H), 1.94-1.85 (m, 1H), 1.39 (br s, 9H). LCMS: 586 [M+H].

Provenance & Evidence