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

Participants

Reaction Conditions

Reaction Steps

(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (500 mg, 1.01 mmol), tetrakis(triphenylphosphine)palladium(0) (174 mg, 0.15 mmol), lithium chloride (128 mg, 3.02 mmol), and copper(I) iodide (58 mg, 0.3 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added 2-(tributylstannyl)-4-chloropyrimidine (447 mg, 1.11 mmol) in dioxane (12 mL) and the resulting mixture was stirred at 90° C. for 18 h. The reaction mixture was 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 C26H26Cl2N3O3S (M+H+): 530.1; Found: 530.0 (M+H+).

Provenance & Evidence