Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(4-(1,5-dimethyl-1H-pyrazol-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

(S)-ethyl 2-(2-(4-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (50.0 mg, 0.087 mmol), 1,5-Dimethyl-1H-pyrazole-4-boronic acid, pinacol ester (24.7 mg, 0.105 mmol), tetrakis(triphenylphosphine)palladium(0) (15.1 mg, 0.013 mmol), and K2CO3 (36.2 mg, 0.262 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 (0.8 mL) and degassed water (0.2 mL). The reaction mixture was stirred at 100° C. for 2.5 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 C33H35ClN3O3S (M+H+): 588.2; Found: 588.3 (M+H+).

Provenance & Evidence