Category: pyridine-derivatives

Electric Literature of 113293-71-3, 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.113293-71-3, name is (6-Aminopyridin-3-yl)methanol, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

To a stirring of (6-aminopyridin-3-yl)methanol (1.24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0 mmol) in EtOH (10 mL) at room temperature was added conc sulfuric acid (10.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C. overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1H NMR (400 MHz, d6-DMSO) delta 9.16 (d, J=6.8 Hz, 1H), 8.26 (s, 1H), 7.67 (s, 1H), 7.19 (dd, J=1.6, 6.8 Hz, 1H), 5.57 (t, J=6.4 Hz, 1H), 4.63 (d, J=6.0, 2H), 4.36 (q, J=7.2 Hz, 2H), 1.35 (t, J=6.8 Hz, 3H). MS m/z 221.1 (M+1)+.

Statistics shows that 113293-71-3 is playing an increasingly important role. we look forward to future research findings about (6-Aminopyridin-3-yl)methanol.

Reference:
Patent; MOLTENI, Valentina; PETRASSI, Hank Michael James; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; NABAKKA, Juliet; NGUYEN, Bao; YEH, Vince; US2013/59832; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 23056-33-9, name is 2-Chloro-4-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-4-methyl-5-nitropyridine

Zinc (15.97 g, 244.0 mmol) was suspended in acetic acid (240 ml) and cooled to 0C. Solid 2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylethenamine (5.56 g, 24.42 mmol) was added portion- wise over about 5 minutes and then the reaction mixture was placed under an atmosphere of argon. The reaction was stirred for 18 h, after which time LCMS analysis indicated that the reaction was complete. The mixture was filtered through Celite, washing with EtOAc. The filtrate was concentrated to give a brown oil. The reaction mixture was partitioned between EtOAc and IN NaOH. The aqueous layer was extracted with EtOAc (3x) and the combined organic layer was dried over Na2S04, filtered and concentrated. The residue was adsorbed onto silica gel and purified by flash column chromatography on silica gel, eluting with EtOAc/isohexane (0-100%) to give 2.79 g of an off-white solid, that is approximately a 10: 1 mixture of the title compound along with 5-methoxy-lH-pyrrolo[2,3-c]pyridine as a minor impurity. The mixture was taken forward into the next step as is. LRMS (ESI) calc’d for (C7H5C1N2) [M+H]+, 153; found 153

With the rapid development of chemical substances, we look forward to future research findings about 23056-33-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; FISCHER, Christian; KATZ, Jason, D.; WILLIAMS, Theresa, M.; ZHANG, Xu-Fang; ZHOU, Hua; WO2013/181075; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884495-14-1 ,Some common heterocyclic compound, 884495-14-1, molecular formula is C7H7BrN2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

DMF-DMA (600 mL) was slowly added to a stirred and heated (80 C) solution of 5-bromo-2- methoxy-4-methyl-3-nitropyridine (134 g, 0.54 mol) in DMF (1.1 L). After addition, the mixture was heated at 95 C for 5 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled to room temperature and poured into ice-cold water (3 L). The resulting red solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (167 g, 100% yield) as red solid. 1H NMR (400 MHz, DMSO-tM): delta 8.24 (s, 1 H), 7.05 (d, J= 13.6 Hz, 1 H), 7.05 (d, J= 13.6 Hz, 1 H), 4.80 (d, J= 13.2 Hz, 1 H), 3.88 (s, 3 H), 2.90 (s, 6 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-14-1, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HSIAO-WEI TSUI, Vickie; HEWITT, Michael, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F., Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (251 pag.)WO2016/77375; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 13466-38-1, name is 5-Bromopyridin-2-ol. A new synthetic method of this compound is introduced below.

Example 142 To a solution of 5-bromopyridin-2-ol (1.0 g, 5.75 mmol) in DMF (10 mL) at RT, potassium tert-butoxide (0.68 g, 6.07 mmol) was added and the mixture was stirred for 30 min. To this mixture, (bromomethyl)cyclopropane (1.03 g, 8.62 mmol) was added, and the resulting mixture was stirred at 70 C. for 2 h. The mixture was allowed to cool to RT, diluted with EtOAc (50 mL) and quenched with water (20 mL). The organic layer was washed with water (2*20 mL) and brine (20 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to afford 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one. 1-(Cyclopropylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one was prepared in analogous fashion to Example 140, except 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one was used in place of 5-bromo-1-ethylpyridin-2(1H)-one. Compound 232 was prepared from compound 8 in analogous fashion to Example 140, except 1-(cyclopropylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one was used in place of 1-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one. ESI-MS m/z: 530.3 [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,13466-38-1, its application will become more common.

Reference:
Patent; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 95727-86-9, name is 5-(Trifluoromethyl)picolinonitrile, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-(Trifluoromethyl)picolinonitrile

Preparation Example 6 The same procedure as in Preparation Example 5 was repeated except that 20 g of 2-cyano-5-trifluoromethylpyridine was used in place of 2-cyano-3-chloro-5-trifluoromethylpyridine, to obtain 15 g of 5-trifluoromethylpyridine-2-carboxylic acid.

The synthetic route of 95727-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ishihara Sangyo Kaisha, Ltd.; US4367336; (1983); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 96424-68-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 96424-68-9, name is 2-Bromo-3-chloropyridine. A new synthetic method of this compound is introduced below.

A mixture of 2-bromo-3-chloropyridine (203.8 g, 1.06 moles), sodium tert-amylate (147 g, 1.27 moles), tert-butyl (3R)-3-aminopiperidine-1-carboxylate (249.5 g, 1.25 moles) in toluene (2 L) was heated to 80 C. To this solution was added chloro(di-2-norbornylphosphino)(2-dimethylaminoferrocen-1-yl) palladium (II) (6.1 g, 10.06 mmol) followed by heating to 105 C. and holding for 3 h. The reaction mixture was cooled to room temperature, 1 L of water was added, then the biphasic mixture was filtered through Celite. After layer separation, the organic phase was washed with 1 L of water followed by treatment with 60 g of Darco G-60 at 50 C. The mixture was filtered through Celite, and concentrated to a final total volume 450 mL, resulting in the precipitation of solids. To the slurry of solids was added 1 L of heptane. The solids were collected via filtration and then dried to afford the title compound as a dull orange solid (240.9 g, 73% yield).1H NMR (CDCl3) delta 8.03 (m, 1H), 7.45 (m, 1H), 6.54 (m, 1H), 5.08 (br s, 1H), 4.14 (br s, 1H), 3.85-3.30 (m, 4H), 2.00-1.90 (m, 1H), 1.80-1.55 (m, 4H), 1.43 (br s, 9H).UPLC (UPLC-MS Method 1): tR=0.72 min.MS (ES+) 312.0 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96424-68-9, 2-Bromo-3-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; Darout, Etzer; Dullea, Robert; Hawkins, Julie Jia Li; Londregan, Allyn T.; Loria, Paula M.; Maguire, Bruce; McClure, Kim F.; Petersen, Donna N.; Piotrowski, David W.; US2014/315928; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58530-53-3, 2,4-Dibromopyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of 2,4-Dibromopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2,4-Dibromopyridine

Preparation of 4-bromo-2-phenylpyridine Into a 500 mL round-bottomed flask was placed 2,4-dibromopyridine (9.90 g, 41.8 mmol), phenylboronic acid (5.10 g, 41.8 mmol), and potassium carbonate (11.55 g, 84 mmol) in DME (100 mL). The reaction mixture was diluted with water (40 mL). This was degassed for 30 minutes and Pd(PPh3)4, (0.483 grams, 0.418 mmol) was added and the reaction was stiffed at reflux for 22 hours. The mixture was diluted with brine and ethyl acetate. The organic layer was washed with water, dried and adsorbed onto Celite and chromatographed on a 400 gram column eluted with 0-5% ethyl acetate in hexane giving the desired product (5.30 g, 54%) as clear colorless oil.

The synthetic route of 58530-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universal Display Corporation; Beers, Scott; Xia, Chuanjun; Layek, Suman; Wendt, Harvey; US2014/8617; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1000342-71-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1000342-71-1, name is 6-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below.

General procedure: To a stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine (1.5 g, 7.61 mmol) in DMF (15 mL), KOH (1.27 g, 11.42 mmol) was added at RT. The resulting solution was stirred for 30 min. Then, fert-butyl 3- (bGammaomomethyl)piperidine-1-caoxylate (3.17 g, 22.84 mmol) was added at 0 C, and stirred at RT for 16h. The reaction mixture was diluted with water (70 mL) and extracted with EtOAc (2 x 70 mL), the combined organic layers were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude compound was purified by flash column chromatography and eluted with 30% EtOAc/ pet ether to obtain the title compound (1.6 g, 54%) as an off white solid. LC-MS (method 1): Rt =2.47 min; m/z = 394.24 (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1000342-71-1, 6-Bromo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109-09-1, 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.109-09-1, name is 2-Chloropyridine, molecular formula is C5H4ClN, molecular weight is 113.54, as common compound, the synthetic route is as follows.

General procedure: 20 mL scintillation vial was charged with a solution of MnCl2THF1.6 (3 mol%, 3 mg, 0.012mmol) in 3 mL THF in a glove box. The corresponding electrophile (0.41 mmol, 1 equiv.) andinternal standard, mesitylene (0.41 mmol, 1equiv.), were added. After five minutes of stirring atroom temperature, the Grignard solution (1.2- 2.6 equiv.) was added dropwise and the reactionwas stirred at room temperature. The reaction mixture was removed from the glovebox andquenched with a saturated K2CO3 solution (3 mL) and EtOAc (3 mL). The organic layer wasextracted with EtOAc (3 x 3mL), and dried over MgSO4. The solution was then filtered andconcentrated. The crude product was purified via a silica plug.

The chemical industry reduces the impact on the environment during synthesis 109-09-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Petel, Brittney E.; Purak, Merjema; Matson, Ellen M.; Synlett; vol. 29; 13; (2018); p. 1700 – 1706;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77992-44-0, 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 77992-44-0 as follows.

INTERMEDIATE 1N-(5-Bromopyridin-2-yl)-2-[2-(difluoromethoxy)phenyllacetohydrazideTo a stirred solution of 2-(difluoromethoxy)phenylacetic acid (3.0 g, 14.85 mmol) in DCM (10 mL) at 0C was added triethylamine (4.4 g, 44.5 mmol), followed by EDCI (3.4 g, 21.90 mmol). The reaction mixture was stirred at 0C for 30 minutes. 5-Bromo-2- hydrazinopyridine (3.07 g, 16.4 mmol) was added and the reaction mixture was stirred at room temperature for 12 h, then diluted with DCM. The organic layer was washed with H20 and brine, then concentrated in vacuo. The crude material obtained was triturated with pentane and Et20 to give the title compound (3.90 g, 70%), which was used for the next reaction without any further purification. deltaEta (400 MHz, DMSO-d6) 10.09-9.90 (m, 1H), 8.67-8.44 (m, 1H), 8.12 (d, 1H, J2.4 Hz), 7.66 (dd, 1H, J 9.0, 2.4 Hz), 7.41 (dd, 1H, J7.6, 1.8 Hz), 7.37-7.26 (m, 1H), 7.26-7.09 (m, 3H), 6.58 (d, 1H, J 8.9 Hz), 3.58 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77992-44-0, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BROOKINGS, Daniel Christopher; JACKSON, Victoria Elizabeth; WO2015/86496; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem