Benzophenone imine → (R)-N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-(diphenylmethyleneamino)-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (intermediate A8A) (1.2 mmol) in toluene (15 ml) was added subsequently at 22° C. and under a argon atmosphere benzophenone imine (2.4 mmol), sodium tert-butoxide (3.6 mmol) and 2-di-t-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.12 mmol). To the mixture was added tris(dibenzylideneacetone) dipalladium chloroform adduct (0.036 mmol), the tube was sealed and heated to 105° C. for 3 h. The mixture was cooled to 22° C., partitioned between saturated aqueous NaHCO3 and ethyl acetate, the organic layer was dried and evaporated to give the crude (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-(diphenylmethyleneamino)-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (A9A) as a yellow oil. MS (ISN): m/z=738.5 [M−H]−.

Provenance & Evidence