Pyridine-derivatives

Synthetic Route of 824-52-2, 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.824-52-2, name is 5-Methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H8N2, molecular weight is 132.16, as common compound, the synthetic route is as follows.

Reference Example 2041,3-dimethyl-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-1-yl)-1H-pyrazole-4-carbaldehydeTo a solution of 5-methyl-1H-pyrrolo[2,3-b]pyridine (1.70 g) in N,N-dimethylformamide (30 mL), which was cooled at 0 C. in an ice bath, was added 60% sodium hydride (in oil, 561 mg) with stirring, and the mixture was stirred at 0 C. for 30 min. 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (1.85 g) was added to this reaction mixture at 0 C., and the reaction mixture was stirred at 80 C. for 6 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography (hexane-ethyl acetate 70:30, v/v), and crystallized from hexane-ethyl acetate to give the title compound (1.42 g, yield 48%) as colorless crystals.1H-NMR (300 MHz, CDCl3) delta:2.46 (s, 3H), 2.54 (s, 3H), 3.68 (s, 3H), 6.69 (d, J=3.6 Hz, 1H), 7.25-7.29 (m, 1H), 7.80-7.83 (m, 1H), 8.19 (d, J=2.1 Hz, 1H), 9.57 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 824-52-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tawaraishi, Taisuke; Imoto, Hiroshi; Cho, Nobuo; US2008/194617; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 824-51-1, 6-Methyl-1H-pyrrolo[2,3-b]pyridine, 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, 824-51-1, blongs to pyridine-derivatives compound. Recommanded Product: 6-Methyl-1H-pyrrolo[2,3-b]pyridine

A mixture of 5-bromoJ-inethyI-2-((2(trimethylsiiyi)ethoxy)methyi)-2H4ndazole(Intennectiate 13, 0.25 rnL, 0.76 rnmoi), 6-methyF-1Hpyrrolo2,3-b]pyridine (100mg, 076 rnrnoi), IPd(ll) cinnamy1)Cl]2 (24 mg, 0.045 mmol), BippyPhos (47 mg, 0091 mmol), and sodium tertbutoxide (105 mg, 1 06 mmoi) in I ,4-dioxane (5 mL) was heated in a microwave reactor at 180 C for 2.0 minutes. The reaction mixture was diluted with 1-120 and extracted with EtOAc (5 mL x 3). The organic layer was dried (Na2SO4) and concentrated in vaeuo. Purification FCC, Si02, 0:100 to20:80. EtOAc:Hex) afforded the title compound (251 rng, 85%). MS (ESI): mass calcd. for C22H28NOSi, 392.2; mz found, 393.2 [M+Hi.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,824-51-1, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 934279-60-4, 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. 934279-60-4, name is 2-Chloro-5-(trifluoromethyl)nicotinaldehyde. A new synthetic method of this compound is introduced below.

To a stirred solution of 427 2-chloro-5-(trifluoromethyl)nicotinaldehyde (780 mg, 3.72 mmol) in 139 MeOH (5 mL) was added 100 NaBH4 (141 mg, 3.72 mmol) at 0 C. and the reaction was stirred at 0 C. for 1 h. The reaction mixture was quenched with sat. 101 NH4Cl (5 mL), then extracted with EtOAc (5 mL×2). The organic layers were collected, washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash silica gel chromatography to give the 429 title compound as an oil. MS (ESI) m/z: 212.0 [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,934279-60-4, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59020-10-9, 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. 59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, 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.

34a. 5-(3-Pyridinyl)-6-chloro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine (from Example 23a, 500 mg, 1.28 mmol) in toluene (10.0 mL) was added 3-pyridinyltributyltin (564 mg, 1.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.039 mmol). After being refluxed overnight, the resulting mixture was cooled to room temperature. Solvent was removed and the residue was chromatographed on a silica gel column, eluding with hexane/EtOAc 2:1 and 1:1 to afford an oil (428 mg, 86%). MS (CI/NH3) m/z 390 (M+H)+. 1 H NMR (CDCl3, 300 MHz) delta1.24-1.67 (m, 2H), 1.44 (s, 9H), 1.86-2.10 (m, 2H), 3.32-3.45 (m, 2H), 3.95-4.27 (m, 3H), 7.28-7.44 (m, 2H), 7.81-7.86 (m, 1H), 8.14-8.17 (m, 1H), 8.65-8.73 (m, 2H).

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 59020-10-9, 3-(Tributylstannyl)pyridine.

Reference:
Patent; Abbott Laboratories; US5629325; (1997); A;; ; Patent; Abbott Laboratories; US6127386; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19235-89-3, 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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile, molecular formula is C6H3ClN2, 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 A15 A teflon capped vial was charged with 4-amino-3-fluorophenol (0.291 g, 2.29 mmol) and anhydrous DMF (2.3 mL). The resultant solution was de-gassed in vacuo and backfilled with argon (3*). The vial was treated with sodium tert-butoxide (0.27 g, 2.41 mmol) under argon and quickly capped. The reaction mixture was stirred at RT for 1 h. After addition of 4-chloropicolinonitrile (0.317 g, 2.29 mmol) and K2CO3 (0.174 g, 1.26 mmol), the vial was de-gassed again and heated in a 90 C. oil bath overnight. The reaction mixture was diluted with EtOAc (60 mL) and washed with brine (25 mL). The aqueous phase was back-extracted with EtOAc (50 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography to afford 4-(4-amino-3-fluorophenoxy)picolinonitrile (0.162 g, 31% yield) as a colorless oil. 1H NMR (DMSO-d6) delta 8.56 (d, J=5.6 Hz, 1H), 7.62 (d, J=2.0 Hz, 1H), 7.14 (dd, J=6.0, 2.8 Hz, 1H), 7.03 (dd, J=11.6, 2.4 Hz, 1H), 6.88-6.77 (m, 2H), 5.25 (s, 2H); MS (ESI) m/z: 230.0 (M+H+).

According to the analysis of related databases, 19235-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; US2008/90856; (2008); 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. 39856-57-0, name is 2,6-Dibromopyridin-3-amine, molecular formula is C5H4Br2N2, 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: C5H4Br2N2

Sodium methoxide (176.2 g, 3.26 mol) was added in portions to a sol. of 3-amino-2,6- dibromopyridine (100 g, 939 mmol) in 1,4-dioxane (1 1) and the r.m. was stirred under reflux for 3 h. After cooling, the r.m. was poured onto a sat. aq. NH4C1 aq. sol (1 1). Additional NH4CI (150 g) and H20 (1 1) were added and the r.m. was stirred at r.t. for 30 min. Et20 (2 1) was added and the r.m. was stirred for 30 min. The layers were separated and the aq. layer was diluted with H20 (1.5 1) and further extracted with Et20 (6 x 0.5 1). The combined o.l. were treated with brine (2 x 0.5 1), dried (MgS04) and cone, under reduced pressure to give a black residue. The residue was purified by flash chromatography over silicagel (glas filter, eluent DCM). The product fractions were combined and cone, under reduced pressure to afford an orange-brownish solid residue. Yield: 67.2 g of intermediate 24 (78.3 %).

With the rapid development of chemical substances, we look forward to future research findings about 39856-57-0.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; DE CLEYN, Michel, Anna, Jozef; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; WO2011/86098; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 348640-02-8, 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 348640-02-8 as follows.

A solution of 209-2 (50.0 g, 183.8 mmol) in dry THF cooled to -78 C. and n-BuLi (81 ml, 2.5 M in hexane) was added over 20 minutes. The resulted solution was maintained at -78 C. for 1 h, and then a solution of BrCl2CCCl2Br (71.0 g, 220.5 mmol) in dry THF was added. The mixture was stirred -78 C. for 30 min and allowed to warm slowly to room temperature. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic layer was dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography (5% ethyl acetate in petroleum ether to 20% ethyl acetate in petroleum ether as the eluent) to afford 209-3 (37 g, 58% yield). MS-ESI: m/z=351.0 [M+1]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,348640-02-8, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; US2009/318455; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 107351-82-6, name is 2-Bromo-5-phenylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 107351-82-6

General procedure: Intermediate M1 (43.6 g, 0.1 mol), iodobenzene (24.5 g, 0.12 mol), CuI (3.3 g, 17.1 mmol), K3PO4 (21.8 g, 102.9 mmol), ethylenediamine (2.3 ml, 34.3 mmol) and toluene (500 ml) were mixed.After stirring for 1 day under reflux, after the reaction was completed, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate (EA) and distilled under reduced pressure. the obtained distillation residue was subjected to column separation (eluent: EA/hexane), compound A1 (35.7 g, 70.1%) was obtained.

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, 107351-82-6, 2-Bromo-5-phenylpyridine.

Reference:
Patent; Wuhan Shengchengyu Technology Co., Ltd.; Huang Yupeng; Qin Wei; Gao Dewen; Tan Yao; (19 pag.)CN109096281; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.

A stirred mixture of 16-1 (170 mg, 459 mumol), 23-1 (124.8 mg 918 mumol) and Potassium phosphate (211 mg, 918 mumol) in Dioxane:water (6:1, 7 mL) was degassed with argon for 10 minutes. PdCl2dppf.DCM (38 mg, 45.9 mumol) was added and stirred the reaction was stirred at 110C for 16 hours, cooled to room temperature and then filtered through a short bed of celite. The filtrate was diluted with Ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-5% Ethyl acetate in Hexane) to afford 23-2 (160 mg, 419 mumol, 91%) as a sticky solid. LC MS: ES+ 382.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98139-15-2, 4-Aminopicolinonitrile, 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, COA of Formula: C6H5N3, blongs to pyridine-derivatives compound. COA of Formula: C6H5N3

Ethyl 4-chlorosulfonyl-3-fluoro-l-methyl-pyrrole-2-carboxylate (1500 mg, 5.56 mmol) was dissolved in dry pyridine (26.25 mL, 325.2 mmol). l-(trifluoromethyl)cyclopropan-l -amine (1392 mg, 11.1 mmol) was added and the mixture was stirred at 70C for 6 hours. The mixture was concentrated in vacuo. The obtained residue was purified by silica gel column (0877) chromatography using gradient elution from heptane to EtOAc (100:0 to 0: 100) yielding ethyl 3-fluoro- 1 -methyl-4-[[ 1 -(trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (1.21 g) as a beige powder. Ethyl 3-fluoro-l-methyl-4-[[l- (0878) (trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (0.15 g, 0.31 mmol) and (0879) 4-aminopyridine-2-carbonitrile (40.05 mg, 0.34 mmol) were dissolved in THF (3 mL) in a tube. The tube was flushed with nitrogen, capped with a septum and stirred at room temperature. To this was added lithium bis(trimethylsilyl)amide (0.76 mL, 1 M, 0.76 mmol) at once using a syringe. The obtained solution was stirred for 3 hours. Then ammonium chloride (aq. / sat. / 10 mL) was added and the layers where separated. Then it was extracted once using ethyl acetate (10 mL). The combined extracts were concentrated in vacuo and purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The obtained fractions were concentrated in vacuo and repurified by Prep HPLC on (RP SunFire Prep CI 8 OmicronBeta-10muetaiota,30chi150etaiotaetaiota). Mobile phase (0.25% NH4HCO3 solution in water, MeOH). The desired fractions were concentrated under reduced pressure and co-evaporated twice with methanol (2 X 20 mL) and dried in a vacuum oven at 55C for 18 hours resulting in compound 192 (51 mg) as a white powder. Method B: Rt: 0.90 min. m/z: 430.1 (M-H)” Exact mass: 431.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.14 – 1.30 (m, 4 H), 3.75 – 3.89 (m, 3 H), 7.57 (d, J=4.6 Hz, 1 H), 7.90 (dd, J=5.6, 2.1 Hz, 1 H), 8.21 (d, J=2.0 Hz, 1 H), 8.63 (d, J=5.7 Hz, 1 H), 9.15 (br. s., 1 H), 10.67 (br. s., 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem