Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate. A new synthetic method of this compound is introduced below., Safety of Methyl 6-bromo-5-fluoropicolinate
[0265] Pent-l-yne (0,524 g, 7,69 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.450 g, 0.64 mmol) was added to copper(I) iodide (0.122 g, 0,64 mmol), TEA (1.787 mL, 12.82 mmol) and methyl 6-bromo-5-fluoropicolinate (1.5 g, 6.41 mmol) in acetonitrile (20 mL) under nitrogen. The resulting mixture was stirred at 80 C for 3 hours. The solvent was removed under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford methyl 5-fluoro-6-(pent-l-yn-l-yl)picolinate (1.28 g, 90 %) as a orange solid. XH NMR (400 MHz, CDCb) delta ppm 8.20 – 8.06 (m, 2H), 7.52 (dd, J = 8.6, 8.0 Hz, 2H), 4.14 (q, J = 7.1 Hz, 1H), 4.01 (s, 7H), 2.50 (td, J = 7.1, 1.0 Hz, 4H), 2.07 (s, 1H), 1.71 (h, J = 7.3 Hz, 4H), 1.28 (t, J = 7.1 Hz, 1H), 1.09 (t, J = 7.4 Hz, 6H). LC-MS (Method A): m/z (ES+), [M+H]+ = 222.2; acid, HPLC tR = 1.140 min.
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Reference:
Patent; ASTRAZENECA AB; CUMMING, John, Graham; WU, Frank, Xinhe; EDMAN, Karl, Henrik; CHEN, Hongming; BROWN, Dean, Gordon; BURLI, Roland, Werner; JOHNSTONE, Shawn, Donald; BROWN, Giles, Albert; TEHAN, Benjamin, Gerald; TEOBALD, Barry, John; CONGREVE, Miles, Stuart; (187 pag.)WO2017/194716; (2017); A1;,
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