Application of 849758-12-9, A common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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.
To a solution of methyl 4-bromo-3-fluorobenzoate (526 mg, 2.26 mmol) in dioxane (10 mL) and H20 (2 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)- 1H-pyrazole- 1 -carboxylate (797 mg, 2.71 mmol), K3P04 (958 mg, 4.51 mmol) and XPhos-G2-Pd-preCat (35.5 mg, 0.045 mmol) at rt. The reaction was stirred under N2 at 60 C overnight. The reaction mixture was diluted with EtOAc,washed with H20 and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The crude product was purified by normal phase chromatography to give two products as white solids. Intermediate 151A (463 mg, 64%): ?H NMR (400MHz, CDC13) oe 8.51 (d,J=1.5 Hz, 1H), 8.10 (s, 1H), 7.84 (dd,J=8.1, 1.5 Hz, 1H), 7.79 (dd, J=11.4, 1.5 Hz, 1H), 7.63 (t,J=7.8 Hz, 1H), 3.92 (s, 3H), 1.68 (s, 9H). LC-MS(ESI) m/z:321.0 [M+H]. Intermediate 151B (175 mg, 35%): ?H NMR (400MHz, CDC13)oe 8.06(d, J=1.8 Hz, 2H), 7.85 (dd,J=8.1, 1.8 Hz, 1H), 7.80 (dd,J11.7, 1.5 Hz, 1H), 7.66 (t,J7.7 Hz, 1H), 3.94 (s, 3H). LC-MS(ESI) m/z: 221.0 [M+H].
The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
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