Triphenylphosphine → 2-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-{2-(4-quinolinyloxy)ethyl}-6H-dipyrido[3,2-b:2',3'-e] [1,4]diazepin-6-one

Participants

Reaction Steps

Diethyl azodicarboxylate (DEAD) (83 μL, 0.53 mmol) was added drop-wise to a solution of 2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (125 mg, 0.38 mmol), 4-hydroxyquinoline (76.3 mg, 0.53 mmol) and Ph3P (138 mg, 0.53 mmol) in THF (2.5 mL) at room temperature. The mixture was stirred at room temperature for 3 h then was concentrated under reduced pressure. The residue was dissolved in EtOAc (60 mL) and the solution was successively washed with 1 N aqueous NaOH (3×10 mL) and brine (15 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:MeOH, 9:1) to give the title compound (52 mg, 30% yield) as a white solid: MS (ESI) m/z 460/462 (MH)+.

Provenance & Evidence