Lithium Chloride → (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (S)-methyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (496.3 mg, 1.03 mmol), tetrakis(triphenylphosphine)palladium(0) (178.2 mg, 0.15 mmol), lithium chloride (43.6 mg, 1.03 mmol), and copper(I) iodide (58.7 mg, 0.31 mmol) and the vial was evacuated and backfilled with argon (3×). To this mixture was added 2-chloro-4-(tributyl)stannyl pyrimidine (456.3 mg, 1.13 mmol) in 1,4-dioxane (10 mL). The reaction mixture was heated at 90° C. overnight, then cooled, filtered through Celite (ethyl acetate eluent), and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+ calc'd for C25H23Cl2N3O3S (M+H+): 516.1; Found: 516.2 (M+H+).

Provenance & Evidence