Benzophenone imine → HCID 90025426, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-bromo-2-fluorophenyl)-5-methyl-5,6-dihydro-2H-1,4-thiazin-3-amine (1.67 g, 2.76 mmol, Eq: 1.00), sodium tert-butoxide (795 mg, 8.27 mmol, Eq: 3), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (85.6 mg, 82.7 μmol, Eq: 0.03) and 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (117 mg, 276 μmol, Eq: 0.1) in toluene (22.0 ml) at 23° C. was added benzophenone imine (1.00 g, 926 μl, 5.52 mmol, Eq: 2) this reaction mixture was stirred under argon atmosphere at 105° C. for 5 hours. Extracted with water and ethyl acetate, dried the organic layer over Na2SO4, filtered off and evaporated totally. The crude material was purified by silica gel flash chromatography with n-heptane and ethyl acetate to give the (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-(diphenylmethyleneamino)-2-fluorophenyl)-5-methyl-5,6-dihydro-2H-1,4-thiazin-3-amine (1.59 g, 2.25 mmol, 81.7% yield) as a yellow oil. MS (ISP): m/z=706.3 [M+H]+.

Provenance & Evidence