Category: 903522-29-2

Reference of 903522-29-2, 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.903522-29-2, name is 3,5-Difluoroisonicotinic acid, molecular formula is C6H3F2NO2, molecular weight is 159.09, as common compound, the synthetic route is as follows.

3,5-Difluoropyridine-4-carboxylic acid (0.510 g, 3.14 mmol) was added to anoven dried 250 mL round bottom flask. The flask was sealed with a septum, purged with nitrogen, and anhydrous THF (50mL) was added. Next, triethylamine (0.542 mL, 3.77 mmol) was added via syringe. The solution was sonicated until itbecame homogeneous, then ethyl chloroformate (0.372 mL, 3.77 mmol) was added. The reaction was stirred for 30 min.before being filtered through a short pad of Celite into a separate oven dried 250 mL round bottom flask. NaBH4 (0.261 g,6.91 mmol) was added followed by MeOH (5 mL). The reaction was stirred for 45 min. at room temperature. A samplealiquot was taken from the reaction, dissolved in HPLC grade MeCN (1 mL), and analyzed with LC-MS to confirm thecompletion of the reaction. The reaction was quenched with sat. ammonium chloride and diluted with EtOAc (150 mL).The organic layer was washed with DI water (50 mL) and brine, then dried over sodium sulfate and condensed to give a yellow oil. The oil was dissolved in DCM and purified by flash chromatography (5 g SiO2 cartridge, 0-12% MeOH/DCMgradient) to give the title compound as a clear semisolid (0.285 g, 63%). This compound has been previously reported andcharacterized (CAS 924649-16-1). 1H NMR (300 MHz, CDCl3) d = 4.81 (s, 2H), 8.28 (s, 2H) 8.30 (s, 2 H).

Statistics shows that 903522-29-2 is playing an increasingly important role. we look forward to future research findings about 3,5-Difluoroisonicotinic acid.

Reference:
Article; Porter, Jacob D.; Vivas, Oscar; Weaver, C. David; Alsafran, Abdulmohsen; DiMilo, Elliot; Arnold, Leggy A.; Dickson, Eamonn J.; Dockendorff, Chris; Bioorganic and Medicinal Chemistry Letters; vol. 29; 23; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.903522-29-2, name is 3,5-Difluoroisonicotinic acid, molecular formula is C6H3F2NO2, molecular weight is 159.09, as common compound, the synthetic route is as follows.COA of Formula: C6H3F2NO2

Synthesis of 3-Butyl-5-fluoro-isonicotinic acid [A067] 3,5-Difluoro-isonicotinic acid (0.557 g, 3.5 mmol) was suspended in anhydrous THF (8 mL) at 0C, under an atmosphere of nitrogen. To this was added butyl magnesium chloride (2.0 M in diethyl ether, 5.25 mL, 10.5 mmol) dropwise over 10 minutes. The suspension slowly changed form during the slow addition with preliminary agglomeration of solid then the solid started to dissolve slowly, achieving full solution around completion of addition of reagent. The reaction mixture was allowed to warm to room temperature and stirred over 72 hours to form a thick yellow suspension. Diluted with water and transferred into a single neck flask and concentrated in vacuo. The yellow solid was diluted with water (10 mL) and EtOAc (10 mL). The pH was adjusted pH~2, by dropwise addition of HC1 (cone.) and extracted with EtOAc (x3 – some of the yellow colour goes into organics). Combined organics were washed with brine (xl), dried (MgSC^) and concentrated in vacuo to yield the title compound [A067] as an orange gum/solid (0.402g) that solidifies slowly: NMR: (1H, 300MHz, d6-dmso); 8.52 (1H, s), 8.42 (1H, s), 2.67 (2H, t), 1.58-1.48 (2H, m), 1.35-1.22 (2H, m), 0.87 (3H, t); LCMS method: 1, RT: 1.22 min, MI 198 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,903522-29-2, 3,5-Difluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; CEPHALON, INC.; CANCER RESEARCH TECHNOLOGY LIMITED; BRESLIN, Henry, J.; DORSEY, Bruce, D.; DUGAN, Benjamin, J.; FOWLER, Katherine, M.; HUDKINS, Robert, L.; MESAROS, Eugen, F.; MONCK, Nathaniel, JT; MORRIS, Emma, L.; OLOWOYE, Ikeoluwa; OTT, Gregory, R.; PAVE, Gregoire, A.; ROFFEY, Jonathan, R. A.; SOUDY, Christelle, N.; TAO, Ming; ZIFICSAK, Craig, A.; ZULLI, Allison, L.; WO2014/52699; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.903522-29-2, name is 3,5-Difluoroisonicotinic acid, molecular formula is C6H3F2NO2, molecular weight is 159.09, as common compound, the synthetic route is as follows.Recommanded Product: 903522-29-2

General procedure: DMF (10 mg, 0.137 mmol) was added to a mixture of 3-fluoropicolinic acid (162 mg, 1.15 mmol) in anhydrous CH2Cl2 (3 mL). The mixture was cooled in an ice bath and then treated with oxalyl chloride (0.1 mL, 1.14 mmol) dropwise. The reaction mixture was warmed to r.t. overnight. A mixture of 3-chloro-N1-methyl-4-nitrobenzene-1,2-diamine (Intermediate 2, 208 mg, 1.03 mmol) and triethylamine (0.16 mL, 1.15 mmol) in anhydrous CH2Cl2 (3 mL) was then added, and the mixture was stirred at r.t. for 2 hrs. The solvent was concentrated under vacuum, and the residue was dissolved in DMSO (2 mL) and stirred at 60 C. for 3 hrs. After cooling to r.t., water was added and the solid precipitate was collected via filtration, washed with water, and air dried. The crude product obtained was used directly in the next step without further purification.; This compound was prepared according to a modified procedure described for Intermediate 3, using 3,5-difluoroisonicotinic acid instead of 3-fluoropicolinic acid as starting material. Following the addition of DMSO, concentrated HCl (1 mL) was added and the mixture was stirred at 80 C. for 3 hrs. LCMS calculated for C13H8ClF2N4O2 (M+H)+: m/z=325.0; Found: 324.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,903522-29-2, 3,5-Difluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Nguyen, Minh; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Qinda; Yao, Wenqing; (72 pag.)US2019/315717; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem