3-(2-Acetamidyl)phenylboronic acid pinacol ester synthesis

Yield:843646-72-0 78%

Reaction Conditions:

with potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;1,1'-bis(diphenylphosphino)ferrocene in 1,4-dioxane at 90; for 18 h;Inert atmosphere;

Steps:

16

In a Schlenk tube, a mixture of 2-(3-bromophenyl)acetamide (1.0 g, 4.67 mmol), bis(pinacolato)diboron (2.37 g, 9.34 mmol) and potassium acetate (1.38 g, 14 mmol) was dissolved in dioxane (40ml). The mixture was purged (vacuum-argon three times) and [1,1-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloromethane complex (0.19 g, 0.23 mmol) and 1,1'-bis(diphenylphospheno)ferrocene (0.13 g, 0.23 mmol) were added. The mixture was purged again (vacuum-argon three times) and stirred at 90 °C for 18 h. The suspension was filtered off and the filtrated diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, and dried over anhydrous sodium sulphate. Solvent was removed in vacuum and the residue was purified by the SP1 automated purification system to give 0.95 g (3.64 mmol) of the desired compound. Yield = 78% HPLC/MS (15 min) retention time 6.28 min. LRMS: m/z 262 (M+1)

References:

EP2196465,2010,A1 Location in patent:Page/Page column 30