Water → tert-butyl {1-[4-(9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

Participants

Reaction Steps

A mixture of 3-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine (1.48 g, 4.7 mmol), tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutyl}carbamate (2.12 g, 5.7 mmol), sat.NaHCO3 (4 mL), and tetrakis(triphenylphosphine)palladium(0) (0.55 g, 0.47 mmol) in toluene-ethanol (1/1, 40 mL) was heated to refluxed temperature for 15 hours. After cooling to room temperature the reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration the solvent was evaporated in vacuo. The crude product was purified by silica gel chromatography (hexane/ethyl acetate) to give a yellow solid (quant.). 1HNMR (CDCl3) 400 MHz δ: 8.09-8.06 (m, 2H), 7.39 (s, 1H), 7.37(d, J=8.0 Hz, 2H), 7.30 (td, J=7.6, 1.5 Hz, 1H), 7.15 (d, J=8.0 Hz, 2H), 7.16-7.10 (m, 1H), 6.98 (dd, J=8.0, 1.2 Hz, 1H), 6.95 (d, J=8.0 Hz, 1H), 6.70 (dd, J=7.7, 4.9 Hz, 1H), 6.27 (s, 1H), 5.08 (s, 1H), 2.57-2.39 (m, 4H), 2.18-2.07 (m, 1H), 1.93-1.84 (m, 1H), 1.48-1.19 (brs, 9H); LC/MS [M+H]: 480.

Provenance & Evidence