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

Participants

Reaction Steps

Diethyl azodicarboxylate (DEAD) (77 μL, 0.49 mmol) was added drop wise to a solution of 2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)4methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (125 mg, 0.38 mmol), 5-hydroxyquinoline (70.9 mg, 0.49 mmol) and Ph3P (128 mg, 0.49 mmol) in THF (2.5 mL) at room temperature. After 1.5 h, additional amounts of DEAD (35 μL, 0.22 mmol) and PPh3 (59 mg, 0.22 mmol) were added to the mixture. The mixture was stirred at room temperature for 1 h then was diluted in EtOAc (50 mL) and the solution was successively washed with aqueous 1 N NaOH (4×10 mL) and brine (15 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2:acetone, 85:15). The resulting solid was triturated with Et2O to give the title compound (38 mg, 22% yield) as a white solid: MS (ESI) m/z 460/462 (MH)+.

Provenance & Evidence