Category: pyridine-derivatives

Reference of 13534-98-0, 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 13534-98-0, name is 4-Amino-3-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 3-Prop-1-ynyl-pyridin-4-ylamine (LXXIII). To a solution of LXXII (1.5 g, 8.67 mmol) in N,N-dimethyl formamide (20 mL) was added solid sodium acetate (2.1 g, 0.02106 mol). The resulting mixture was degassed for 10 min and then [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.31 g, 0.430 mmol), followed by tributyl(prop-1-yn-1-yl)stannane (3.7g, 11.3 mmol), were added. The reaction mixture 25 was heated at 100 C in a sealed tube for 12 h, before being allowed to cool to room temperature. The reaction mixture was poured in to water and the mixture was extracted 157 of 363 {//– DRAFT –//4069/3020WO/00228726/v2} 4069.3020 WO with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The crude product mixture was purified by column chromatography on (100-200 mesh) silica, using 3% methanol in dichloromethane as the eluant to afford LXXIII (1 g, 87%) as a semi solid.1H NMR (400 MHz, CDCl3) delta 8.29 5 (s, 1H), 8.08 (d, 2H, J= 5.7 Hz), 6.50 (d, 2H, J= 5.6 Hz), 4.61 (brs, 2H), 2.11 (s, 3H); MS (ESI, positive mode) m/z 133 (MH+).

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 13534-98-0, 4-Amino-3-bromopyridine.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; CULLEN, Matthew; HAUCK, Sheila; GENG, Bolin; FOLEY, Megan; BASTOS, Cecilia, M.; MUNOZ, Benito; HAEBERLEIN, Markus; WO2015/73528; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53014-84-9, 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.53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, molecular weight is 121.1366, as common compound, the synthetic route is as follows.

154. (+)-2- 3,4-trans)-4-methyl-l-g6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- f] ri,2,41triazin-4(3H)-one [1113] To a stirred solution of (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (150 mg, 0.49 mmol) in MeOH (10 mL) was added 6-methylnicotinaldehyde (71 mg, 0.59 mmol) at room temperature and stirred for 2 h under argon atmosphere. To the resulting solution was added NaCNBH3 (93 mg, 1.48 mmol) and stirring was continued for another 8 h at room temperature. The volatiles were evaporated under reduced pressure. The residue was diluted with water and extracted with CH2CI2 (2 x 20 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-((6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5, 1 -f [ 1 ,2,4]triazin- 4(3H)-one (43 mg, 21%) as an off-white solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.38 (s, 1H), 7.67 (s, 1H), 7.58 (d, 1H), 7.21 (d, 1H), 3.97-3.91 (m, 2H), 3.64-3.59 (m, 2H), 3.52-3.49 (m, 1H), 2.94-2.92 (m, 1H), 2.87-2.84 (m, 2H), 2.79-2.71 (m, 2H), 2.67-2.61 (m, 2H), 2.42 (s, 3H), 2.24-2.21 (m, 1H), 1.87-1.82 (m, 4H), 1.09 (d, 3H); Mass (ESI): 409.3 [M++l]; LC-MS: 96.82%; 409.4 (M++l); (column; Eclipse XDB C-18, (150×4.6 mm, 5.0mu); RT 5.58 min. 0.05% TFA (Aq): ACN; 1.0 ml/min); UPLC (purity): 98.45%; (column; Acquity UPLC HSS-T3, 100×2.1 mm, 1.8mu; RT 2.83 min. 0.025% TFA (Aq): ACN; 0.30 ml/min; Chiral HPLC: 99.61%, R,= 9.69 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) 0.1% DEA in n-Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D20: + 18.96 (c = 0.25, DCM). TLC: 5% MeOH/DCM (Rf: 0.3).

The chemical industry reduces the impact on the environment during synthesis 53014-84-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67515-76-8, 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. 67515-76-8, name is Methyl 5-aminopicolinate, molecular formula is C7H8N2O2, 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 62 Preparation of methyl 5-fluoropicolinate STR225 The methyl 5-aminopicolinate (2.2 g) is dissolved in 5.5 ml 48% fluoroboric acid and 20 ml 95% ethanol. This mixture is cooled, with stirring, to -3 C. and then 1.81 g n-butyl nitrite added dropwise. After a further one-half hour at -3 C., 0.5 ml n-butyl nitrite is added slowly and stirring continued for one-half hour at 0 C. After adding 20 ml ether carefully, the mixture is rapidly filtered, and the solid washed twice with cold hexane. The solid is suspended in 100 ml heptane, and the suspension slowly heated with stirring. At about 60 C., a vigorous exothermic reaction occurs. Heating is then continued to 80 C. A red oil separates on the sides of the flask. The heptane solution is filtered, and the filtrate concentrated to give the desired product. The red oil is dissolved in water, excess sodium bicarbonate solution added, and the solution extracted with ethyl acetate. The ethyl acetate extract is washed with saturated brine, dried and concentrated. The residue is chromatographed on silica gel and the product, methyl 5-fluoropicolinate, eluted with 1:1-ether:hexane. This material is used directly for the preparation of the picolinic 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 67515-76-8, Methyl 5-aminopicolinate.

Reference:
Patent; American Cyanamid Company; US4638068; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1104455-41-5, name is Methyl 4-chloro-5-methylpicolinate. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

To a stirred solution of methyl 4-chloro-5-methylpicolinate (220 mg, 1.2 mmol) in DMSO (10 mL) purged and maintained under an inert atmosphere of N2, was added Cu504.5H20 (15 mg, 0.06 mmol.), KOH (336 mg, 6 mmol) and a solution of 1,2-ethanedithiol (226 mg, 2.4 mmol) in water (1 mL). The resulting solution was heated to 90 oC overnight, cooled to 25 oC and concentrated to afford the crude title compound. MS (ES) m/z 170 (M+H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1104455-41-5, Methyl 4-chloro-5-methylpicolinate.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; HUDSON, Ryan; BEAUSOLEIL, Anne-Marie; (616 pag.)WO2018/89261; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 96166-00-6 ,Some common heterocyclic compound, 96166-00-6, molecular formula is C12H12N2O, 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.

A toluene solution (331 g) of the obtained 2-amino-5-benzyloxypyridine,Ethanol (217 g) and 10% Pd / C (2.28 g, moisture content 53%) were charged in an autoclave and reacted at 25 C. for 4 hours while being introduced at 0.2 MPa (absolute pressure) in a hydrogen atmosphere.After completion of the reaction, Pd / C was filtered and the residue was washed with ethanol (76 g).The filtrate was dried under reduced pressure to obtain 2-amino-5-hydroxypyridine (25.6 g, 0.23 mol) (yield 92%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 96166-00-6, 5-(Benzyloxy)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KOEI CHEMICAL COMPANY LIMITED; TAKAHASHI, SATOSHI; NIHEI, YURI; (24 pag.)JP2017/48131; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1003-68-5, 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 1003-68-5 as follows.

A mixture of Cul (0.19 g, 1 mmol), Cs2C03(6.85 g, 20 mmol) and ethyl 2-oxocyclohexanecarboxylate (0.34 g, 2 mmol) in DMSO (10 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 5-methylpyridone (1.09 g, 10 mmol) and 4-(2-fluoro-4-iodobenzyl) morpholine (3.21 g, 10 mmol) in DMSO (12 mL) via syringe. The reaction mixture was heated at 100 C overnight, cooled to rt and filtered. The filtrate diluted with H20 (50 mL) was extracted with CH2C12(50 mL x 3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE / EtOAc (V / V) = 10 : 1) to give the title compound as a white solid (0.70 g, 23%). The compound was characterized by the following spectroscopic data:MS (ESI, pos.ion) m/z: 303.2 (M+l);-NMR (400 MHz, CDC13): delta 2.06 (s, 3 H), 3.16-3.32 (m, 4 H), 3.86-3.97 (m, 4 H), 4.44 (s, 2 H), 6.47 (d, 1 H, J = 9.6 Hz), 7.39-7.44 (m, 2 H), 7.48 (s, 1 H), 7.52-7.55 (m, 1 H), 7.99 (t, 1 H, J= 8.2 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; WANG, Xiaojun; LIN, Runfeng; CAO, Shengtian; WANG, Zhaohe; LI, Jing; WO2014/12360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 941294-57-1, 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.941294-57-1, name is 5-Bromo-2-iodo-4-methylpyridine, molecular formula is C6H5BrIN, molecular weight is 297.92, as common compound, the synthetic route is as follows.

To a suspension of 5-bromo-2-iodo-4-methylpyridine(1g, 3.36 mmol) in NMP (6mL) with an inert atmosphere of argon, KF (0.585 g, 10.07 mmol), Cul (1.92 g, 10.08 mmol) and CF3SiMe3 (2.49 mL, 15.07 mmol) were added. The resulting solution was stirred overnight at 60C. After cooling, the mixture was poured into 12% aqueous ammonia, and then extracted with Et2O. The organic solutions were combined, dried over MgSO4, filtered and concentrated. Purification of the crude residue by normal phase chromatography (0% to 100%, hexane – diethyl ether) afforded the desired product (23% yield) as a yellow oil.

Statistics shows that 941294-57-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-iodo-4-methylpyridine.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Gonzalez Rodriguez, Jacob; Gual Roig, Silvia; Esteve Trias, Cristina; Vidal Gispert, Laura; EP2738172; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 13362-78-2, name is (E)-1,2-Di(pyridin-4-yl)ethene, molecular formula is C12H10N2, 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. COA of Formula: C12H10N2

General procedure: Equimolar amounts of 1,10-diiodoperfluorodecane (1e) and dipyridyl 2a or its ethylene analogue 2b were dissolved in a vial containing chloroform at room temperature and in a vial. The open vial was closed in a cylindrical bottle containing paraffin oil. Chloroform was allowed to diffuse at room temperature and after two days 1e·2a,b were isolated as white crystals, washed with n-pentane, and characterized.

With the rapid development of chemical substances, we look forward to future research findings about 13362-78-2.

Reference:
Article; Catalano, Luca; Metrangolo, Pierangelo; Pilati, Tullio; Resnati, Giuseppe; Terraneo, Giancarlo; Ursini, Maurizio; Journal of Fluorine Chemistry; vol. 196; (2017); p. 32 – 36;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19437-26-4, 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 19437-26-4 as follows.

General procedure: Two drops of glacial acetic acid as a catalyst were added to themixtures of thiosemicarbazides (0.5 mmol) and di(2-pyridyl) ketone,2-pyridinecarboxaldehyde, 2-quinolinecarboxaldehyde, 8-hydroxy-2-quinolinecarboxaldehyde or 2-quinoxalinecarbaldehyde (0.5 mmol) in ethanol (5 ml). The glasstubes were sealed and placed into a microwave reactor at 83 C for20 min (the reactor power did not exceed 50W). The final productswere crystallized from dry methanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19437-26-4, its application will become more common.

Reference:
Article; Mrozek-Wilczkiewicz, Anna; Malarz, Katarzyna; Rejmund, Marta; Polanski, Jaroslaw; Musiol, Robert; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 180 – 194;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 98400-69-2, 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. 98400-69-2, name is 4-(Boc-Amino)pyridine. A new synthetic method of this compound is introduced below.

8.1 1,1-Dimethylethyl (3,5-dibromopyrid-4-yl)carbamate A mixture of 1,1-dimethylethyl 4-pyridinecarbamate (11.0 g; 57.0 mmol) and N-bromosuccinimide (25.6 g; 142.0 mmol) in acetonitrile (50 ml) is heated for 12 hours at 55° C. The reaction mixture is concentrated under reduced pressure. The residue obtained is taken up in ether (400 ml), washed with saturated aqueous potassium bicarbonate solution (2*200 ml), dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue is chromatographed on a column of silica, eluding with an ethyl acetate/cylohexane gradient of from 0 to 10percent ethyl acetate. 8.2 g of 1,1-dimethylethyl (3,5-dibromopyrid-4-yl)carbamate are isolated in the form of a white solid. Yield (percent)=41

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98400-69-2, its application will become more common.

Reference:
Patent; Altenburger, Jean-Michel; Cremer, Gerard; Lassalle, Gilbert; Matrougui, Mostafa; US2003/207920; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem