Benzophenone imine → HCID 86670223, compound

Participants

Reaction Conditions

Reaction Steps

In a tube under an atmosphere of argon a solution of [bis-(4-methoxy-phenyl)-phenyl-methyl]-[(S)-5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-yl]-amine (356 mg, 518 μmol) in toluene (5 ml) was treated successively with sodium tert-butoxide (149 mg, 1.55 mmol), 2-di-tertbutylphosphino-2′,4′,6′-triisopropylbiphenyl (33 mg, 77.7 μmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (26.8 mg, 26 μmol), and benzophenonimine (188 mg, 1.04 mmol). The tube was sealed and the mixture was heated at 105° C. under stirring for 4 hours. For the workup, the brown solution was extracted with ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and evaporated at reduced pressure. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate 100:0 to 50:50 as the eluent. The {(S)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-yl}-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine (207 mg, 51% yield) was obtained as a light yellow foam. MS (ISN): m/z=786.5 [M−H]−.

Provenance & Evidence