Category: pyridine-derivatives

Electric Literature of 832735-60-1, 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 832735-60-1 as follows.

Example 444 (1538) N-tert-Butyl-3?-fluoro-4?[1,2,4]triazolo[4,3-a]pyridin-7-ylbiphenyl-2-sulfonamide (1539) To a 20 mL vial were added N-(tert-butyl)-3?-fluoro-4?-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1?-biphenyl]-2-sulfonamide (45 mg, 0.10 mmol), 7-bromo-[1,2,4]triazolo[4,3-a]pyridine (21 mg, 0.10 mmol) K2CO3 (29 mg, 0.21 mmol), Pd(dppf)Cl2.CH2Cl2 (4 mg, 0.005 mmol), and a stir bar. The vial was sealed with a teflon lined cap and the vial sparged with N2. The vial was then charged with freshly sparged DMSO (2 mL) and stirred for 16 hours at 80 Celsius. The reaction mixture was then cooled to rt, filtered, and purified by HPLC to give the title compound (30 mg, 53%). MS (ESI): mass calcd. for C22H21FN4O2S, 424.14; m/z found, 425.1 [M+H]+. 1H NMR (400 MHz, CD3OD) delta 9.40 (s, 1H), 8.79 (s, 1H), 8.20-8.11 (m, 2H), 7.77 (m, 1H), 7.70-7.57 (m, 3H), 7.47-7.38 (m, 3H), 1.10 (5, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,832735-60-1, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Bacani, Genesis M.; Eccles, Wendy; Fitzgerald, Anne E.; Goldberg, Steven D.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Lee-Dutra, Alice; Liu, Jing; McClure, Kelly J.; Meduna, Steven P.; Pippel, Daniel J.; Rosen, Mark D.; Sales, Zachary S.; US2015/259357; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 144584-32-7 , The common heterocyclic compound, 144584-32-7, name is 3-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, 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.

Example 96 2-Chloro-3-bromo-4-(cis-4-phenylcyclohexylamino)-pyridine 2.27 g (10 mmol) of 2,4-dichloro-3-bromopyridine, 2.6 g (15 mmol) of cis-4-phenylcyclohexylamine and 0.1 g of ammonium chloride are heated at 120 C. for 10 hours in 10 ml of N-methylpyrrolidone. After cooling, saturated sodium hydrogencarbonate solution is added and the reaction product is extracted with ethyl acetate. Purification is carried out by column chromatography. Yield: 1.9 g (52%); m.p. 105 C. 1 H-NMR (CDCl3): delta: 7.96 (d, 1H), 7.18 to 7.36 (m, 5H), 6.42 (d, 1H), 5.36 (d, 1H), 3.85 (m, 1H), 2.65 (m, 1H), 1.5 to 2.2 (m, 8H) ppm.

The synthetic route of 144584-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Schering AgrEvo GmbH; US5723450; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 942189-65-3, 2-(6-Bromopyridin-3-yl)pyrimidine, 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, 942189-65-3, blongs to pyridine-derivatives compound. SDS of cas: 942189-65-3

Example 31 To a stirred solution of 10 (3.05g, 12.9 mmol) in DMF (30 mL) 1 (5.97 mL, 38.7 mmol) and DIPEA (8.5 mL, 51.7 mmol) was added. The clear mixture was heated at 80 C overnight before concentrated to a small volume and partitioned between ethyl acetate and brine. The separated organic layer was dried and concentrated to dryness. The resulting crude was purified on silica gel column (eluting with 15% to 30% ethyl acetate in hexanes) to yield 11 as a brown solid (4.5 g, 84%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942189-65-3, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; ZHU, Hugh, Y.; DESAI, Jagdish, A.; COOPER, Alan, B.; DOLL, Ronald, J.; WO2011/41152; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 957187-27-8, 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. 957187-27-8, name is 8-Bromo-6-chloroimidazo[1,2-a]pyridine, molecular formula is C7H4BrClN2, 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.

b) 8-(benzylthio)-6-chloroimidazo[1,2-a]pyridine A mixture of 8-bromo-6-chloroimidazo[1,2-a]pyridine (2.50 g), benzylmercaptan (1.40 mL), tris(dibenzylideneacetone)dipalladium(0) (248 mg), 1,1′-bis(diphenylphosphino)ferrocene (298 mg), DIPEA (3.8 mL) and toluene (20 mL) was stirred under a nitrogen atmosphere at 100 C. for 2 hr. The reaction mixture was filtered to remove an insoluble material and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.01 g). 1H NMR (300 MHz, DMSO-d6) delta 4.47 (2H, s), 7.13 (1H, d, J=1.8 Hz), 7.22-7.39 (3H, m), 7.39-7.47 (2H, m), 7.59 (1H, d, J=1.1 Hz), 7.93 (1H, d, J=1.2 Hz), 8.64 (1H, d, J=1.9 Hz).

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 957187-27-8, 8-Bromo-6-chloroimidazo[1,2-a]pyridine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3279-76-3, 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. 3279-76-3, name is 6-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, 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.

PREPARATION 133 2-Methoxy-6-methylpyridine Trimethyloxonium tetrafluoroborate (10.0 g, 67.6 mmol) was added portionwise to a suspension of 6-methylpyridin-2-one (7.3 g, 67.0 mmol) in dichloromethane (100 ml), and once addition was complete, the reaction was stirred at room temperature for 24 hours. Dichloromethane (50 ml) and aqueous sodium hydroxide solution (50 ml, 2N) were added and the layers separated. The aqueous phase was extracted with dichloromethane (2*50 ml), the combined organic solutions washed with brine (50 ml), dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using an elution gradient of pentane: dichloromethane (66:34 to 0:100) to afford the title compound (2.25 g, 27%) as a colourless oil. delta (CDCl3): 2.49 (3H, s), 3.90 (3H, s), 6.38-6.73 (2H, m), 7.23-7.40 (1 H, br d).

According to the analysis of related databases, 3279-76-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6251904; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54916-65-3, 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. 54916-65-3, name is 5-Chloro-2-methoxynicotinic acid, molecular formula is C7H6ClNO3, 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.

5-Chloro-2-methoxy-pyridine-3 -carboxylic acid (182 mg, 0.97 mmol) and 6-[4-[(lS)- 2,2,2-trifluoro-l-methyl-ethyl]-l,2,4-triazol-3-yl]pyridin-2-amine (250 mg, 0.97 mmol) were dissolved in triethylamine (1.35 mL, 9.72 mmol). Propylphosphonic anhydride (> 50 wt % in EtOAc, 1.0 mL) was added and the reaction was heated at 80 C for 3 h. The reaction was cooled to rt, quenched by addition of MeOH (5 mL) and stirred for 1 h. The resulting solid was filtered and dried under vacuum to give the title compound (200 mg, 48 %) as a white solid. 1H NMR (400 MHz, CDCI3) d 10.37 (s, 1H), 8.58 (d, 7=2.51 Hz, 1H), 8.43 – 8.49 (m, 2H), 8.31 (d, 7=2.51 Hz, 1 H), 8.16 (dd, 7=0.75, 7.78 Hz, 1H), 7.95 (t, 7=7.91 Hz, 1H), 6.71 (quin, 7=7.22 Hz, 1H), 4.19 (s, 3H), 1.82 (d, 7=7.28 Hz, 3H). MS (ESI): 427.0 [M + H]+.

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 54916-65-3, 5-Chloro-2-methoxynicotinic acid.

Reference:
Patent; BIOGEN MA INC.; GONZALEZ LOPEZ DE TURISO, Felix; DECHANTSREITER, Michael; XIN, Zhili; JONES, John, H.; HIMMELBAUER, Martin; (0 pag.)WO2020/6031; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866807-27-4, Adding some certain compound to certain chemical reactions, such as: 866807-27-4, name is 3-Amino-6-chloropyridine-2-carboxylic acid,molecular formula is C6H5ClN2O2, 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 866807-27-4.

[0173j To a solution of 3-amino-6-chloropicolinic acid (860 mg, 4.98 mmol) in dichloromethane (50 ml) was added azetidin-3-ol hydrochloride (580 mg, 5.29 mmol), HATU (2.27 g, 5.98 mmol) and Et3N (1.5 g, 14.95 mmol). The reaction mixture was stirred at 20 C for 2 h. After 2 h, the reaction mixture was concentrated in vacuo and the crude product was purified via flash chromatography on silica gel (0-50% ethyl acetate in petroleum ether) to provide (3 -amino-6-chloropyridin-2-yl)(3 -hydroxyazetidin- 1 -yl)methanone (1.1 g, 73% yield) as a yellow solid. LCMS (ESI) [M+H] = 228.0.

According to the analysis of related databases, 866807-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; HEFFRON, Timothy; MALHOTRA, Sushant; WEI, BinQing; CHAN, Bryan; GAZZARD, Lewis; GANCIA, Emanuela; LAINCHBURY, Michael; MADIN, Andrew; SEWARD, Eileen; HU, Yonghan; (101 pag.)WO2018/167147; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885168-20-7, 2-Bromo-5-fluoro-4-methylpyridine, 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, Computed Properties of C6H5BrFN, blongs to pyridine-derivatives compound. Computed Properties of C6H5BrFN

5-fluoro-4-methyl-pyridine-2-carboxylic acid methyl ester18 g 2-bromo-5-fluoro-4-methyl-pyridine, 1.5 g 1, ?-bis (diphenylphosphino) ferrocene dichloropalladium (II) and 18 g sodium acetate was stirred 17 h at 80C and 5 bar carbon monoxide. The reaction was filtered and the solvent was removed. Diethylether was added to the residue and the mixture was filtered. The filtrate was evaporated to give 12 g desired product. Rt: 0.90 min. (method AB)(M+H)+: 170

The synthetic route of 885168-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WO2013/79460; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 64951-08-2, 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. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

Production Example 3 N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (242 mg), imidazo[1,2-a]pyridine-2-carboxylic acid (194 mg), EDC.HCl (199 mg), HOBt (138 mg), dimethylformamide (5 mL) and triethylamine (0.33 mL) was stirred overnight at room temperature. The solvents were distilled off under reduced pressure and following extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and, thereafter, the solvents were concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (286 mg). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.58-1.97 (m, 4H) 3.35-3.58 (m, 2H) 3.92-4.04 (m, 2H) 4.70-5.75 (m, 3H) 6.75-7.66 (m, 7H) 8.00-8.24 (m, 2H) (ESI pos.) m/z: 420 ([M+H]+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2012/10414; (2012); 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. 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine, the common compound, a new synthetic route is introduced below. name: 2-Bromo-6-(chloromethyl)pyridine

2-Chloro-6-bromomethyl-pyridine was prepared from 2-chloro-6-methylpyridine [(638] mg, 5.0 mmol) with NBS (996.5 mg, 5.6 mmol) and AIBN (92 mg) in tetrachlorocarbon. [3-{5-] [[1- (6-CLROMO-PYRIDIN-2-YLMETHYL)-PIPERIDIN-2-YL]- [L,] 2,4] oxadiazol-3-yl}-benzonitrile (450 mg, quantitative) was obtained from [3- (5-PIPERIDIN-2-YL- [1,] 2,4] oxadiazol-3-yl) -benzonitrile (300 mg, 1.18 mmol) with crude 2-chloro-6-bromomethyl-pyridine (640 mg, 3.12 mmol) and diisopropylethylamine (762.5 mg, 5.0 mmol) in DMF (8 mL) at 80 [C] for [18] [H. IH] NMR [(CDC13),] [8] (ppm): 8.40 (d, 1H), 8.33 (dd, 1H), 7.79 (dd, 1H), 7.62 (q, 2H), 7.49 (d, [1H),] 7.18 (d, [1H),] 4.16 (t, [1H),] 3.75 (dd, 2H), 3.04 (m, [1H),] 2.49 (m, [1H),] 2.04 (m, 2H), 1.50-1. 86 (m, 4H).

The synthetic route of 727356-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14902; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem