With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.128071-77-2, name is 4-Bromo-2-fluoronicotinaldehyde, molecular formula is C6H3BrFNO, molecular weight is 204, as common compound, the synthetic route is as follows.Safety of 4-Bromo-2-fluoronicotinaldehyde
To a solution of ethyl prop-2-ynoate (2.92 g, 29.8 mmol) in THF (100 mL) at -78 C under N2was added LDA (14.9 mL of a 2M solution in THF/heptane/ethylbenzene, 29.8 mmol) dropwise. The mixture was stirred at -78 C for 20 minutes and a solution of 4-bromo-2-fluoro-pyridine-3-carbaldehyde (5.79 g, 28.38 mmol) in THF was added. The mixture was stirred at -78 C for 1 h and the reaction was quenched by the addition of saturated aqueous NH4C1 (100 mL). The mixture was extracted with EtOAc (3 x 100 mL) and the combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound (1.47 g, 4.87 mmol, 17% yield) as a red oil. LCMS m/z = 302.0 [M+Hf ?H NMR (400 MHz, CDC13):oe ppm 1.32 (t, J = 7.2 Hz, 3 H), 3.08 (dd, J = 9.2, 2.8 Hz, 1H), 4.26 (q, J = 7.2 Hz, 2H), 6.04 (dd, J =9.1, 1.9 Hz, 1H), 7.49-7.44 (m, 1H), 8.05 (dd, J = 5.3, 0.8 Hz, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,128071-77-2, 4-Bromo-2-fluoronicotinaldehyde, and friends who are interested can also refer to it.
Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; REN, Albert S.; SCHRADER, Thomas O.; KASEM, Michelle; ZHU, Xiuwen; (182 pag.)WO2018/35477; (2018); A1;,
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