Potassium Carbonate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(5-methoxypyridin-3-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

The reaction mixture of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy) phenyl)benzo[d]thiazol-6-yl)ethyl pivalate (20 mg, 0.029 mmol), 3-methoxypyridine-5-boronic acid pinacol ester (10 mg, 0.043 mmol), 2N K2CO3 (70 μL), Pd(PPh3)4 (3.3 mg, 0.0029 mmol) in dioxane (1 mL) was heated at 120° C. in sealed tube for 2 hours. After the reaction finished, the reaction was cooled down, to the reaction mixture was added MeOH (1 mL), 2N NaOH (500 μL) and heated at 45° C. for 3 hours. Then reaction mixture was washed by sat. NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product (10 mg, 62%). LCMS-ESI+: calc'd for C32H31ClN2O3S: 559.2 (M+H+); Found: 559.2 (M+H+).

Provenance & Evidence