17100-63-9, A common compound: 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
To a solution of methyl 4-iodo-3-methoxybenzoate (9) (0.5 g, 1.71 mmol) and tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate(0.70 g, 2.05 mmol) in 1,4-dioxane (10.0 mL) was added 2.0 mL of water. The reaction mixture was degassed with argon for about30 min. After that Pd(dppf)Cl2.DCM (0.069 g, 0.085 mmol) andNa2CO3 (0.36 g, 3.42 mmol) were added to the reaction mixture andagain degassed with argon for another 20 min. The reactionmixturewas stirred under reflux for 3 h. After cooled down to roomtemperature, the mixture was extracted with EtOAc, washed withbrine, dried over Na2SO4, and concentrated under reduced pressure.The crude product was purified by column chromatography(Hexane/EtOAc 4:6) to afford 10 as a yellow solid (0.52 g, 79.7%).1H NMR (500 MHz, CDCl3) delta 8.15 (d, J 5.0 Hz, 1H), 7.85 (s, 1H), 7.65(d, J 10.0 Hz, 2H), 7.56 (d, J 10.0 Hz, 2H), 7.32 (d, J 10.0 Hz, 1H),7.28 (s, 1H), 3.86 (s, 3H), 3.82 (s, 3H), 1.62 (s, 9H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-bromo-3-methoxybenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Naik, Ravi; Valentine, Heather; Hall, Andrew; Mathews, William B.; Harris, James C.; Carter, C. Sue; Dannals, Robert F.; Wong, Dean F.; Horti, Andrew G.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 644 – 656;,
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