Application of 618-89-3,Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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.
Example 18(a)Methyl 3-{[5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-yl]amino}benzoate 5-Fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-amine (obtained from Example 1(b)) (99 mg, 0.42 mmol), methyl 3-bromobenzoate (97 mg, 0.45 mmol) and Cs2CO3 (230 mg, 0.71 mmol) were mixed in anhydrous 1,4-dioxane and the mixture was flushed with argon for 10 minutes before Pd2(dba)3 (23 mg, 0.025 mmol) and X-Phos (24 mg, 0.050 mmol) were added. The mixture was flushed with argon, then heated in a sealed tube at +90-100 C. until the reaction was complete. The reaction mixture was diluted with CH2Cl2, filtered and evaporated. The residue was taken up in CH2Cl2 and the organic phase was washed with H2O. Residual water was removed from the organic phase by treatment with Na2SO4. The crude of the base product was purified using preparative HPLC to give the title compound (97 mg, 62%) as a solid.1H NMR (400 MHz, DMSO-d6) delta ppm 9.73 (s, 1H) 8.57 (d, 1H) 8.19 (t, 1H) 8.04-7.95 (m, 1H) 7.59-7.52 (m, 1H) 7.43 (t, 1H) 7.37 (d, 1H) 5.44-5.31 (m, 1H) 3.84 (s, 3H) 2.51 (s, 3H) 1.42 (d, 3H) 1.40 (d, 3H); MS (ESI) m/z 370 (M+1).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-bromobenzoate, its application will become more common.
Reference:
Patent; AstraZeneca AB; US2008/214560; (2008); A1;,
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