Adding a certain compound to certain chemical reactions, such as: 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 14062-25-0, Application In Synthesis of Ethyl 2-(4-bromophenyl)acetate
To a solution of 6-(((2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)-1 ,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile (for a preparation see Intermediate 5) (1 .67 g, 3.86 mmol), ethyl 2-(4-bromophenyl)acetate (1.127 g, 4.64 mmol) and potassium carbonate (1.602 g, 1 1 .59 mmol) in toluene (10 mL) and ethanol (10.0 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.446 g, 0.386 mmol) under nitrogen. The reaction mixture heated at 100 C for 1 h, then partitioned between EtOAc and water. The layers were separated and the aqueous phase was extracted with EtOAc (x3). The combined organic layers were washed with brine, dried (MgS04), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25g), eluting with an EtOAc / cyclohexane gradient (10 to 80%). The appropriate fractions were combined and concentrated in vacuo to give ethyl 2-(4-((2S,4/?)-1-acetyl-4- ((5-cyanopyridin-2-yl)amino)-2-methyl-1 ,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate (752 mg, 42%) as a viscous colourless oil. LCMS (Formate, 2min), Rt=1 .10min, MH+ = 469.
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Reference:
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; DEMONT, Emmanuel Hubert; MITCHELL, Darren Jason; WATSON, Robert J; WO2012/143413; (2012); A1;,
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