These common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, its 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. 106614-28-2
To a 8 mL sealed tube was added (1S,4S,5R)-5-[[l-(2-chloro-6-methylphenyl)-4- cyclopropyl-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptane 8g (100 mg, 0.28 mmol, 1.00 equiv.), methyl 2,4-difluorobenzoate (72 mg, 0.42 mmol, 1.50 equiv.), CsF (0.134 g, 3.00 equiv.), and l-Ethyl-3-methylimidazolium dimethyl phosphate (1 mL). The resulting mixture was heated at 90 C overnight. After cooling to room temperature, the mixture was diluted with 20 mL of H2O, and extracted with ethyl acetate (100 mL x 2). The combined organic extracts were washed with brine (100 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 :2) to afford methyl 4-[(1S,4S,5R)-5-[[l-(2-chloro-6-methylphenyl)-4- cyclopropyl-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan-2-yl]-2-fluorobenzoate 8h (91 mg, 64%) as a red oil.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 106614-28-2.
Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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