942473-59-8 | Pyridine-derivatives

The origin of a common compound about 2,5-Dibromoisonicotinic acid

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 942473-59-8, 2,5-Dibromoisonicotinic acid.

Application of 942473-59-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 942473-59-8, name is 2,5-Dibromoisonicotinic acid, molecular formula is C6H3Br2NO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 1; ethyl 2,5-dibromoisonicotinate (1-2)A solution of 2,5-dibromoisonicotinic acid (KL, 5 g, 17.80 mmol) and sulfuric acid (1.23 mL, 23.1 mmol)in ethanol (100 mL) was heated to reflux overnight. After reducing the volume of ethanol by rotary evaporation to approximately 1A of it’s original volume, the crude reaction mixture was partitioned between 2M sodium carbonate solution and EtOAc, separating layers and washing the organic layer with saturated sodium bicarbonate solution and brine. This solution was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase column chromatography (O to 50% EtOAc in hexanes) to afford the product (I1T) as a dark oil. ESI+ MS [M]+ C8H7Br2NO2 = 308.0.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BERGMAN, Jeffrey, M.; COLEMAN, Paul, J.; MATTERN, Mamio Christa; MERCER, Swati, P.; REGER, Thomas, S.; ROECKER, Anthony, J.; WO2010/51236; (2010); A1;,
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Pyridine | C5H5N – PubChem

The origin of a common compound about 2,5-Dibromoisonicotinic acid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942473-59-8, its application will become more common.

Application of 942473-59-8, 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 942473-59-8 as follows.

2,5-Dibromopyridine-4-carboxylic acid (25.0 g) is dissolved in MeOH (400 ml.) and cone, sulfuric acid (5 ml.) is added dropwise at ambient temperature. The reaction is heated to reflux and stirred for 16 h. After cooling to ambient temperature the solution is concentrated under reduced pressure and partitioned between EtOAc and aq. sat. NaHCO-3. The organic phase is washed with aq. sat. NaHCO-3, dried over Na2S04, solid parts are removed by filtration and concentrated under reduced pressure. Column chromatography of the resulting crude product (ISCO-CombiFlash Rf, cyclohexane/EtOAc) yields the title compound (23.8 g, yield 91 %) as a colorless oil. (2134) H NMR (400 MHz, DMSO-c 6): delta = 8.77 (s, 1 H), 8.01 (s, 1 H), 3.91 (s, 3H) ppm; MS (ESI) m/z 295.9 [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,942473-59-8, its application will become more common.

Reference:
Patent; BASF SE; VOGT, Florian; WITSCHEL, Matthias; SEISER, Tobias; LOPEZ CARRILLO, Veronica; SEITZ, Thomas; KRAEMER, Gerd; KREUZ, Klaus; NEWTON, Trevor William; REINHARD, Klaus; SCHACHTSCHABEL, Doreen; TRESCH, Stefan; (109 pag.)WO2018/19758; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New downstream synthetic route of 2,5-Dibromoisonicotinic acid

Statistics shows that 942473-59-8 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromoisonicotinic acid.

Reference of 942473-59-8, 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.942473-59-8, name is 2,5-Dibromoisonicotinic acid, molecular formula is C6H3Br2NO2, molecular weight is 280.9, as common compound, the synthetic route is as follows.

A 20-L 4-necked round-bottom flask purged and maintained under a N2 atmosphere was charged with 2,5-dibromoisonicotinic acid (1.030 Kg, 3.67 mol, 1.00 equiv), TEA (484 g, 4.78 mol, 1.30 equiv), tert-butanol (10 L) followed by the addition of DPPA (1215 g, 4.41 mol, 1.20 equiv). The resulting solution was stirred overnight at 80 C. This reaction was repeated for 5 times. The resulting mixture was concentrated in vacuo, diluted with 20 L of water and extracted with 3×15 L of EtOAc. The organic layers were combined, washed with 2×15 L of brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with an EtOAc/petroleum ether gradient (1:30 to 1:15) to afford 3.2 Kg (41%) of tert-butyl 2,5-dibromopyridine-4-ylcarbamate (A-3) as a white solid

Statistics shows that 942473-59-8 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromoisonicotinic acid.

Reference:
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem