Acetate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(3,4-dimethoxyphenyl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

Preparation of (S)-ethyl 2-tert-butoxy-247-(4-chlorophenyl)-2-(2-(3,4-dimethoxyphenyl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate: (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (50.0 mg, 0.094 mmol), 3,4-dimethoxyphenylboronic acid (20.6 mg, 0.113 mmol), tetrakis(triphenylphosphine)palladium(0) (16.4 mg, 0.014 mmol), and K2CO3 (39.2 mg, 0.283 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed 1,4-dioxane (1 mL) and degassed water (0.25 mL). The reaction mixture was stirred at 110° C. for 1.5 h, 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 C34H35ClN3O5S (M+H+): 632.2; Found: 632.2 (M+H+).

Provenance & Evidence