Sodium Carbonate → HCID 69087704, compound

Participants

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), methyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (49 mg, 0.18 mmol), Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (6 mg, 0.009 mmol), and 2M Na2CO3 aq. (0.090 mL, 0.18 mmol) in DMF (3 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 (41 mg, 73%) as a yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.16 (dd, J=8.0 Hz and 2.3 Hz, 1H), 8.00-7.99 (m, 1H), 7.53 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 7.30 (td, J=8.0 Hz and 2.9 Hz, 2H), 7.16-7.13 (m, 3H), 6.94 (d, J=8.0 Hz, 1H), 6.81-6.77 (m, 1H), 6.59 (dd, J=8.0, 4.6 Hz, 1H), 6.57-6.54 (m, 1H), 6.24-6.22 (m, 1H), 5.18-5.00 (m, 1H), 3.77 (s, 3H), 2.57-2.48 (m, 4H), 2.19-2.10 (m, 1H), 1.93-1.87 (m, 1H), 1.39 (br s, 9H). LCMS: 629 [M+H].

Provenance & Evidence