Category: pyridine-derivatives

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.898746-42-4, name is 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5FN2, molecular weight is 136.13, as common compound, the synthetic route is as follows.COA of Formula: C7H5FN2

Preparation 23Synthesis of l-ethy lo[2,3-b]pyridine.To a stirred solution of 6-fluoro-lH-pyrrolo[2,3-b]pyridine (15.00 g, 1 10.19 mmol) in DMF (100 mL), under a nitrogen atmosphere, is added potassium carbonate(22.84 g, 165.3 mmol), followed by ethyl bromide (12.36 mL, 165.3 mmol). The reaction is heated to 70 C for 4 h. Further ethyl bromide (3.00 mL, 27.6 mmol) is added and the reaction kept at 70 C overnight. After cooling further potassium carbonate (8.00 g, 57.9 mmol) and ethyl bromide (3.00 mL, 27.6 mmol) are added, and the reaction heated at 70 C for 4 h. The reaction is cooled, poured onto brine (ca. 500 mL) and the product extracted with CHCI3 (ca. 2 x 300 mL). The combined organic extracts are dried over magnesium sulphate, filtered, and concentrated in vacuo to give a brown oil. This is purified by column chromatography on silica, eluting with 0 to 70% DCM in hexane to give the title compound as a light yellow oil (16.38 g, 99.77 mmol). MS (m/z): 165 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,898746-42-4, 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; LAMAS-PETEIRA, Carlos; RICHARDS, Simon, James; SAPMAZ, Selma; WALTER, Magnus, Wilhelm; WO2012/74769; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83393-46-8, 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 83393-46-8 as follows.

To a solution of 3-acetyl, 7-azaindole (320 mg, 2 mmol), thiohydantoin (465 mg, 3 mmol) and BF3.Et2O (1.52 mL, 12 mmol) in dry THF (14 mL), under argon, triethylamine (0.84 mL, 6 mmol) was added dropwise and the reaction mixture stirred for 5 days at RT. The mixture was poured in ice and pH made slightly basic by addition of sodium bicarbonate. The solution was extracted with ethyl acetate, dried over sodium sulfate and concentrated to give an oil that crystallized from ethyl acetate (260 mg, 1 mmol, 50% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83393-46-8, its application will become more common.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/112020; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference 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.

Example 183; N-(4-Fluoro-benzyl)-4-(3-pyridin-3-yl-indole-1-sulfonyl)-benzamide hydrochloride; Combine N-(4-fluoro-benzyl)-4- (3-iodo-indole-1-sulfonyl)-benzamide 300 mg, 0.56 mmol, 1 equiv), 3-tributylstannylpyridine (Frontier Scientific ; 90%; 230 mg (0.90) = 210 mg, 0.56 mmol, 1.0 equiv), and tetrakis (triphenylphosphine) palladium (0) (100 mg, 0.087 mmol, 0.15 equiv) in deoxygenated toluene (3 mL) and heat at 100 C for 18 h. Transfer the reaction solution to a column of silica gel (125 mm x 25 mm dia. ) and elute (0-70% EtOAc/hex) to yield 73 mg (27%) of free amine as an orange oil. Dissolve this material in MeOH (5 mL) and add 12 M aq HCl (2 drops). Rotary evaporate this solution (40 C) to yield 78 mg (27%) ofN-(4-fluoro-benzyl)-4- (3-pyridin-3-yl-indole-1- sulfonyl)-benzamide hydrochloride as a brown glass. MS (m/e): 485.95 (M+1) ; 484.10 (M-1).

According to the analysis of related databases, 59020-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84199-61-1, 3-Acetyl-2-bromopyridine, 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: C7H6BrNO, blongs to pyridine-derivatives compound. COA of Formula: C7H6BrNO

General procedure: An solution of indicated quantity of DAST in dry CH2Cl2 was added dropwise to a solution of 14 (26.9mmol) in dry CH2Cl2 (50mL) at 0C. The reaction mixture was warmed to rt and stirred for indicated period of time. The resulting mixture was poured into H2O (50mL), sat. aq NaHCO3 was added to pH=8, and organic phase was separated. The aqueous layer was extracted with CH2Cl2 (3×50mL), the combined organic layers were dried over Na2SO4, and then evaporated under reduced pressure.

The synthetic route of 84199-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Subota, Andrii I.; Ryabukhin, Sergey V.; Gorlova, Alina O.; Grygorenko, Oleksandr O.; Volochnyuk, Dmitriy M.; Journal of Fluorine Chemistry; vol. 224; (2019); p. 61 – 66;,
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. 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine, molecular formula is C6H5BrClN, 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. Safety of 5-Bromo-3-chloro-2-methylpyridine

A mixture of tert-butyl 2-(3-acetyl-5-(4, 4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)acetate (S2, 100 mg, 1 equiv), 5-bromo-3-chloro-2-methylpyridine (S3, 62 mg, 1.2 equiv), and cesium carbonate (230 mg, 2.8 equiv) in DMF (8 mL) was purged with argon for 5 min. 1,1?-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (14 mg, 0.06 equiv) was then added under argon and the reaction mixture w is heated to 90 C. overnight. The reaction mixture was cooled to room temperature and diluted with EtOAc (20 mL) and water (10 ml). The organic layer was then separated, washed with brine (3×15 mL), dried, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (5% MeOH in DCM) to give 100 mg of tert-butyl 2-(3-acetyl-5-(5-chloro-6-methylpyridin-3-yl)-1H-indol-1-yl)acetate (S4) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 914358-72-8.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, 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 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn (CN) 2 (3.96 g, 33.7 mmol) and Pd (Ph3P) 4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 for 12 h under nitrogen atm. The reaction mixture was cooled to ambient temperature, filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30 ethyl acetate/hexanes to afford the product. 1H NMR (500 MHz, DMSO-d6) , delta 8.69 (s, 1H) , 7.50 (s, 1H) , 4.04 (s, 3H) LC/MS (M+1) + 169.

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; SHI, Zhi-Cai; WALSH, Shawn P.; WU, Zhicai; YU, Yang; FERGUSON II, Ronald; GUO, Zhiqiang; FRIE, Jessica; SUZUKI, Takao; BLIZZARD, Timothy A.; FU, Qinghong; VANGELDER, Kelsey F.; (118 pag.)WO2016/65582; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3475-21-6, 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 3475-21-6, name is 4-Methyl-2-phenylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-phenyl-4-methylpyridine (6 g, 35.4 mmol) and SeO2 (24 g, 216 mmol) were refluxed in pyridine (100 ml) overnight under argon. The mixture was then filtered through celite while hot. The Celite filter cake was rinsed with pyridine (3×50 ml) and the resulting filtrate evaporated to dryness. The solid thus obtained was triturated in water (200 ml) and filtered off. The resulting brown solid was suspended in a mixture of water (150 ml) and MeOH (200 ml) and made basic by addition of an aqueous NaOH solution. The mixture was then filtered over Celite to removed some insoluble materials. The filtrate was then acidified with concentrated HCl. MeOH was evaporated and the formed precipitate was filtered, washed with water, then small portions Of Et2O (3×20 ml) and finally dried to afford 5.9 g (84%) of the titled compound as a slightly brown solid.

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 3475-21-6, 4-Methyl-2-phenylpyridine.

Reference:
Patent; KONINKLIJKE PHILIPS ELECTRONICS N.V.; WO2007/4113; (2007); A2;,
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. 42521-09-5, name is Methyl 2,6-dichloroisonicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2,6-dichloroisonicotinate

Under inert atmosphere, a mixture of methyl 2,6-dichloropyridine-4-carboxylate (2,00 g), dimethylzinc (2N in toluene, 14.6 ml, 3.0 equiv.) and PdCI2(dppf)2 (400 mg, 0.05 equiv.) in dioxane (50 ml), was heated at 80C for 4Hrs. The reaction mixture was cooled by an ice bath, hydrolysed with water (100 ml) and filtered through a pad of celite. The pad was rinsed with water and EtAOc. The filtrate was extracted with EtOAc (250 ml). The organic layer was washed with brine (1 00 ml), dried over MgSO4 and concentrated. Purification by flash chromatography (MeOH in CH2Cl2, 0 to 2%) afforded compound 99 as an orange oil in 96% yield. 1H-NMR (400 MHz, DMSO): 2.51 (s, 6H, 2CH3); 3.88 (s, 3H, O-CH3); 7.51 (s, 2H, Ar). M/Z(M+H)+ = 166.1.

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, 42521-09-5, Methyl 2,6-dichloroisonicotinate.

Reference:
Patent; DOMAIN THERAPEUTICS; MAYER, Stanislas; SCHANN, Stephan; WO2013/174822; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 134363-45-4 , The common heterocyclic compound, 134363-45-4, name is 2-(Pyridin-3-yl)benzoic acid, molecular formula is C12H9NO2, 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.

Step 3: N-(Benzyloxy)-2-pyridin-3-ylbeiizamide; Ethyl 2-bromobenzoate (380 nag, 1.9 ?rmol), O-hydroxylbenzylamine (280 mg, 2.3 mmol), EDC (440 mg, 2.3 mmol), and HOBT (350 mg, 2.3 mmol) were combined in DMF (2 ml) and stirred over the 2 days at room temperature. The reaction was purified by RP-HPLC (C 18 column; H2CVCH3CN with 0.1% TFA) to afford the title compound. 1H NMR (400 MHz, de-DMSO, ppm): delta 11.6 (s, IH), 8.75 (s, IH), 8.72 (d, J= 4.8 Hz, IH), 8.07 (d, J= 8.0 Hz , IH), 7.73 (t, J= 6.6 Hz, IH), 7.63 (t, J= 7.3 Hz, IH)3 7.57-7.51 (m, 3H), 7.44-7.34 (m, 5H) and 4.76 (s, 2H). ES MS: m/z = 305 (M+l).

The synthetic route of 134363-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/10964; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 185017-72-5, 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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-2-chloro-6-methylpyridine (47.8 mg, 0.231 mmol) and 2- (cyclopentylmethyl) oxazole (35 mg, 0.231 mmol) in DMA (1 mL) was added potassium acetate (45.4 mg, 0.463 mmol) and Pd (PPh3)4(26.7 mg, 0.023 mmol) under N2. The reaction mixture was stirred at 90 overnight. The reaction mixture was cooled to room temperature, filtered and the filtration was concentrated in vacuum, the residue was purified by Prep. TLC (PE: EA 10: 1) to give the title compound. MS: 277.1 (M+1) .1H NMR (CDCl3-d, 400 MHz) : delta 7.95 (d, J 7.8 Hz, 1H) , 7.66 (bs, 1H) , 7.16 (d, J 7.8 Hz, 1H) , 2.82 (d, J 7.0 Hz, 2H) , 2.31-2.39 (m, 1H) , 1.83 (bs, 4H) , 1.65 (bs, 2H) , 1.27 (d, J 5.5 Hz, 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 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem