Potassium Carbonate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(3-cyanophenyl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

Participants

Reaction Conditions

Reaction Steps

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate (19.7 mg, 0.034 mmol), 3-cyanophenylboronic acid (6.1 mg, 0.041 mmol), Pd(PPh3)4, and K2CO3 (14.3 mg, 0.103 mmol) were placed 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 (0.4 mL) and degassed water (0.1 mL). The reaction mixture was heated at 110° C. for 1.5 h, cooled, diluted with ethyl acetate, 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 C37H37ClN3O3S: 638.2 (M+H+); Found: 637.9 (M+H+).

Provenance & Evidence