4-Aminocarbonylphenylboronic acid → HCID 68084725, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl]phenyl trifluoromethanesulfonate (30 mg, 0.043 mmol) in toluene (1 mL) and EtOH (1 mL) was added saturated 1M-K3PO4aq, 4-aminocarbonylphenylboronic acid (21 mg, 0.13 mmol) and Pd (PPh3)4 (5 mg, 0.0043 mmol). The reaction was degassed for 2 minutes and then heated at 100° C., 2.5 h. The reaction mixture was cooled to room temperature, then was diluted with EtOAc (15 mL) and washed with brine. The organic phase was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (SiO2, 20% to 50% to 100% EtOAc in hexane) gave the title compound as a white solid (22 mg, 76%); LCMS: 675 [M+H].

Provenance & Evidence