Electric Literature of 959616-64-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 959616-64-9 as follows.
[00672] Intermediate 73c: methyl 5-fluoro-6-methoxy-pyridine-3-carboxylate[00673] Triethylamine (1 .62mL, 11.61 mmol), tetrakis(triphenylphosphine)palladium(0) (0.45g, 0.3gmmol) and formic acid (0.44mL, 11 .61 mmol) were added to a flask containing a stirring solutionof methyl 2-chloro-5-fluoro-6-methoxy-pyridine-3-carboxylate (1 .7g, 7.74mmol) in DMF (1 7mL). The reaction mixture was then heated to 100 C and left to stir for 4 hours. The reaction mixture was left to cool before being filtered through celite and the solvent removed in vacuo. The residue was taken up in EtOAc (5OmL), water (5OmL) added and the organics extracted with further EtOAc (3 x 5OmL). The organic layers were combined, dried over Na2504, filtered and concentrated in vacuo. Theresidue was purified by column chromatography using an eluent of 0-50% EtOAc in heptane) toafford the desired product methyl 5-fluoro-6-methoxy-pyridine-3-carboxylate (590mg, 3.1 9mmol,41% yield) as a white solid.1H NMR (CDCI3,400MHz) O/ppm: 8.61 (1H, d, J= 1.9Hz), 7.88 (1H, dd, J= 10.4Hz, 1.9Hz), 4.09(3H, 5), 3.92 (3H, 5),MS Method 3: RT: 5.10 mm, 186.1 m/z [M+H]
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,959616-64-9, its application will become more common.
Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
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