Some common heterocyclic compound, 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, molecular formula is C11H12N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C11H12N2O3
To a solution of methyl 2-ethoxy-lH-benzo[d]imidazole-7-carboxylate (1.00 g, 4.54 mmol) in 2-propanol (15 ml) was added potassium carbonate (1.26 g, 9.08 mmol) and this was stirred at 30°C for 5 minutes. To this mixture were added 2-(4- (bromomethyl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.44 g, 4.77 mmol) and tetrabutylammonium iodide (0.084 g, 0.227 mmol) and the temperature was increased to 45°C. After stirring for 2.5 hours, another portion of 2-(4-(bromomethyl)phenyl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (0.250 g, 0.842 mmol) was added and the reaction was stirred for an additional 18 hours. The reaction was cooled to RT and diluted with EtOAc (200 ml), and 0 (50 ml) was added. The layers were separated and the organic layer was washed with brine (50 ml), then dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The residue was dissolved in DCM (10 ml) and injected on a 40-gram ISCO-type silica gel column pre-equilibrated with hexane and the title compound was purified by elution using a 0 to 60percent EtOAc/hexane gradient to provide the title compound as a yellow solid. (1.44 g, 3.31 mmol, 72percent yield). LC-MS (Method H): 1.42 min, [M + H]+= 437.2; H NMR (400 MHz, CDC13) delta ppm 7.73 (dd, 7=8.0, 1.0 Hz, 1 H) 7.67 (m, 7=8.2 Hz, 2 H) 7.53 (dd, 7=7.8, 1.2 Hz, 1 H) 7.16 (t, 7=7.8 Hz, 1 H) 6.96 (m, 7=8.2 Hz, 2 H) 5.63 (s, 2 H) 4.65 (q, 7=7.0 Hz, 2 H) 3.72 (s, 3 H) 1.46 (t, 7=7.0 Hz, 3 H) 1.31 (s, 12 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150058-27-8, its application will become more common.
Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
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