Toluene → HCID 86712807, compound

Participants

Reaction Conditions

Reaction Steps

Under argon in a sealed tube were added to a solution of (S)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-4-(5-bromo-2-fluorophenyl)-4-(difluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (intermediate E7.1) (725 mg, 1.16 mmol) in toluene (15 ml) sodium tert-butoxide (334 mg, 3.48 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (73.8 mg, 174 μmol) and tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (60.0 mg, 58.0 μmol) and benzophenone imine (420 mg, 389 μl, 2.32 mmol), the tube was sealed under argon and the mixture was stirred at 105° C. for 4 h. The brown solution was extracted with ethyl acetate/water. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated to give a brown oil. The residue was chromatographed on 20 g silica gel with ethyl acetate 0-50% to give (S)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-4-(difluoromethyl)-4-(5-(diphenylmethyleneamino)-2-fluorophenyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (525 mg, 723 μmol, 62.4% yield) as a yellow oil. MS (ISP): m/z=726.8 [M+H]+.

Provenance & Evidence