Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Chloro-3-fluoroisonicotinic acid
Step A: A mixture of 2-chloro-3-fluoroisonicotinic acid (2.0 g, 10.0 mmol) in thionyl chloride (42 mL) was heated to 80 0C. The homogenous solution was stirred for 2 hours, concentrated under reduced pressure, and pumped dry on high vacuum overnight to give crude 2-chloro-3-fluoroisonicotinoyl chloride. Crude 2-chloro-3-fluoroisonicotinoyl chloride (1.04 g, 5.4 mmol) was added to a stirred solution of JV-(3-amino-2-chloro-4-fluorophenyl)-7V-(4- methoxybenzyl)propane-l -sulfonamide (2.08 g, 5.4 mmol) in anhydrous CHCl3 (15 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched by adding sat. aqueous NaHCO3 solution, followed by extraction with DCM (3X). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified using flash chromatography (gradient elution, solvent: 0-50% ethyl acetate in heptanes) to afford 2-chloro- LambdaL(2-chloro-6-fluoro-3-(N-(4-methoxybenzyl)propylsulfonamido)phenyl)-3- fluoroisonicotinamide (2.75 g, 94%). 1H NMR (500 MHz, DMSO-^6) delta 10.67 (s, IH), 8.44 (d, IH), 7.71 (t, IH), 7.35 (m, 2H), 7.13 (t, 2H), 6.82 (dd, 2H), 4.81 (d, IH), 4.63 (d, IH), 3.70 (s, 3H), 3.37 – 3.20 (m, 2H), 1.80 (d, 2H), 1.01 (dt, 3H). LC/MS: m/z 544.1 [M+l].
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Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25938; (2011); A2;,
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