Triphenylphosphine → HCID 3010649, compound

Participants

Reaction Steps

Diisopropyl azodicarboxylate (DIAD) (131 μL, 0.66 mmol) was added drop-wise to a solution of 11-(cyclopropyl)-5,11-dihydro-2-fluoro-8-(2-hydroxyethyl)-4methyl-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (140 mg, 0.44 mmol), 4-hydroxyquinoline (96.4 mg, 0.66 mmol) and Ph3P (124 mg, 0.66 mmol) in THF (2.2 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 3 N aqueous NaOH (3×20 mL), aqueous saturated NH4Cl (20 mL) and brine (20 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was partially purified by flash chromatography (EtOAc:MeOH; 95:5). The solid was further purified by reverse phase HPLC (CombiPrep ADS-AQ 50×20 mm, 5 μ120 A, 5-100% MeCN+0.10% TFA/water+0.10% TFA in 25 min) to give the bifluoroacetic acid salt of the title compound (104 mg, 43% yield) as a white solid: MS (ESI) m/z 456 (MH)+.

Provenance & Evidence