Benzophenone imine → HCID 58562976, compound

Participants

Reaction Conditions

Reaction Steps

Under argon in a sealed tube was added to a solution of (S)-5-(5-bromo-2-fluoro-phenyl)-5,7,7-trimethyl-[1,4]oxazepan-3-one (intermediate A16A) (1.0 g, 3.0 mmol) in toluene (20 ml), sodium tert-butoxide (NaOBut) (865 mg, 9.0 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (t-Bu X-phos) (127 mg, 10 mol %) and tris(dibenzylideneacetone)dipalladium chloroform complex (Pd2(dba)3.CHCl3) (93 mg, 3 mol %) followed by benzophenone imine (1.07 mL, 6.0 mmol). The tube was sealed under argon and the mixture was stirred at 105° C. for 18 h to 2.5 days. The mixture was cooled to 23° C., poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over sodium sulphate. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the (S)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-one (1.15 g, 88%) as light yellow foam. MS (ISP): m/z=431.3 [(M+H)+].

Provenance & Evidence