1454682-74-6

Method A: 2-Fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamic acid prop-1-en-2-yl ester (6.67 g, 19.90 mmol) was dissolved in dioxane (60 mL) and 3,3-dimethylbutan-1-amine (2.42 g, 23.9 mmol) and 1-methyl pyrrolidine (0.169 g, 1.99 mmol). The reaction mixture was stirred at 75°C overnight. Upon completion of the reaction, the mixture was cooled to room temperature, and the precipitated solid was collected by filtration and washed with ether to afford the target product 1-(3,3-dimethylbutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (6.62 g, 88% yield, two-step total yield). Mass spectrometry (MS) analysis showed m/z: 379.2 ([M+H]+).

[1] Patent: WO2013/134243, 2013, A1. Location in patent: Page/Page column 14
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179