Triethylamine → HCID 67504131, compound

Participants

Reaction Conditions

Reaction Steps

tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (100 mg, 0.179 mmol), triethylamine (0.5 mL), bis(triphenylphosphine)dichloropalladium(II) (38 mg, 0.054 mmol) were dissolved in DMF (3 mL) and MeOH (3 mL). Atmosphere of the mixture was exchanged to CO gas, then heated to 100° C. for 88 hours. 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=1:2×3) to afford the desired product (36 mg, 37%) as a colorless oil. 1HNMR (CDCl3) 400 MHz δ: 8.13 (dd, J=8.0 Hz and 1.7 Hz, 1H), 8.02 (d, J=4.0 Hz, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.33 (td, J=7.4 Hz and 1.7 Hz, 2H), 7.30-7.24 (m, 4H), 7.14 (td, J=7.4 Hz and 1.1 Hz, 1H), 6.95 (d, J=7.4 Hz, 1H), 6.82-6.78 (m, 1H), 6.59 (dd, J=8.0 Hz and 4.6 Hz, 1H), 6.24 (s, 1H), 5.11 (br s, 1H), 3.88 (s, 3H), 2.57-2.42 (m, 4H), 2.17-2.08 (m, 1H), 1.91-1.83 (m, 1H), 1.39 (br s, 9H). LCMS: 538 [M+H].

Provenance & Evidence