1021918-86-4

1. tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate (10.2 mmol), pinacol ester of bis(boronic acid) (11.2 mmol), palladium(II) acetate (1.02 mmol), dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (1.02 mmol), and potassium acetate (30.4 mmol) were mixed in a mixed solution of 1,4-dioxane ( 50 mL) and triethylamine (2 mL) were mixed.2. The reaction mixture was heated at 110 °C overnight.3. Upon completion of the reaction, the mixture was concentrated under vacuum.4. The residue was purified by fast chromatography (eluent: 10% ethyl acetate/petroleum ether) to afford the target product 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1H-1H-1 . radical)-1H-benzo[d]imidazole-1-carboxylic acid tert-butyl ester as solid in 42% yield.

[1] Patent: WO2011/66211, 2011, A1. Location in patent: Page/Page column 71
[2] Patent: WO2009/7751, 2009, A2. Location in patent: Page/Page column 120-121
[3] Patent: WO2008/51493, 2008, A2. Location in patent: Page/Page column 151
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6793 - 6799
[5] Patent: WO2013/28445, 2013, A1. Location in patent: Page/Page column 56; 57