Category: pyridine-derivatives

Synthetic Route of 17282-03-0 ,Some common heterocyclic compound, 17282-03-0, molecular formula is C6H5BrClN, 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.

3-Bromo-2-ethoxy-5-methylpyridine To a solution of 3-bromo-2-chloro-5-methylpyridine (4.00 g, 19.37 mmol) in ethanol (100 mL) was added sodium ethoxide (6.59 g, 96.9 mmol) in three portions. The mixture was stirred under nitrogen at 100 C. for 2 days. The reaction was cooled to room temperature, diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 20%, EtOAc/hexanes) afforded the title compound (3.00 g, 72%). 1H NMR (400 MHz, DMSO-d6) delta 7.94 (dd, J=0.8, 2.3 Hz, 1H), 7.89-7.82 (m, 1H), 4.31 (q, J=7.0 Hz, 2H), 2.18 (t, J=0.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-03-0, its application will become more common.

Reference:
Patent; Bollu, Venkataiah; Breitenbucher, James; Kaplan, Alan; Lemus, Robert; Lindstrom, Andrew; Vickers, Troy; Wilson, Mark E.; Zapf, James; US2014/275531; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1594-57-6, name is N-Hydroxyisonicotinimidamide, molecular formula is C6H7N3O, molecular weight is 137.14, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Example 1: 4- (3-Pyridin-4-yl- [1, 2,4] oxadiazol-5-ylmethoxy) piperidine-1-carboxylic acid tert- butyl ester A stirred solution of triethylamine (123mul, 0. 87mmol) and 4-carboxymethoxypiperidine- 1-carboxylic acid tert-butyl ester (Preparation 1,227mg, 0. 87mmo1) in toluene (10ml) was treated with isobutylchloroformate (113mul, 0. 87mmol). After 20min, activated powdered 3A molecular sieves (0.7g) andN-hydroxyisonicotinamidine (lOOmg, 0. 73mmol) were added and the mixture heated under reflux for 18h. On cooling, the mixture was filtered through celite, the solvent removed in vacuo and the residue purified by flash chromatography (IH-EtOAc, 7: 13) to afford the title compound: RT = 3. 29min ; m/z (ES+) 361.3 [M+H] + ; OH (CDC13) 1.40 (9H, s), 1.55-1. 63 (2H, m), 1.80-1. 92 (2H, m), 3.05-3. 15 (2H, m), 3.64-3. 79 (3H, m), 4.80 (2H, s), 7.90 (2H, d), 8.75 (2H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1594-57-6, N-Hydroxyisonicotinimidamide, and friends who are interested can also refer to it.

Reference:
Patent; PROSIDION LIMITED; WO2005/61489; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 77837-08-2 ,Some common heterocyclic compound, 77837-08-2, molecular formula is C12H9NO3, 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.

d2-5-(Hydroxymethyl)-1-phenylpyridine-2(1H)-one: Isobutyl chloroformate (0.45 mL, 3.49 mmol) was added to a solution of 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid (0.500 g, 2.32 mmol) and N-methylmorpholine (0.38 mL, 3.49 mmol) in tetrahydrofuran (10 mL) at -5° C. The mixture was stirred for 3 hours at the same temperature, diluted with tetrahydrofuran and filtered over a pad of Celite under argon. The filtrate containing the mixed anhydride was added dropwise to a suspension of sodium borodeuteride (0.117 g, 2.79 mmol) in tetrahydrofuran at -10° C. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours, after which D2O (1 mL) was added. Standard extractive work up gave a crude residue which was purified by preparative HPLC to give the title compound as a white solid (0.290 g, 61percent). m.p. 115-120° C.; 1H NMR (400 MHz, CDCl3) delta 2.05 (br, 1H), 6.66 (d, J=9.1 Hz, 1H), 7.25-7.51 (m, 7H); IR (KBr) nu 3337, 1665, 1586, 1535, 1257 cm-1; MS 204 (M+1).

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. 77837-08-2, 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/319026; (2008); 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 3430-17-9, name is 2-Bromo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Bromo-3-methylpyridine

General procedure: To a 10-mL reaction vial, heteroaryl halide (1.0 mmol), boronic acid (1.2 mmol), K3PO4 (2.0 mmol), tetra-butylammonium bromide (TBAB) (0.5 mmol), and 4 (0.1 mol %) in water (3.5 mL) were added. The reaction mixture was stirred at 85 C and the reaction progress was monitored by GC-MS analysis. After completion of the reaction, it was diluted with H2O and CH2Cl2. The organic layer was separated from mixture, the dried organic layer over MgSO4, and evaporated under reduced pressure. The crude reaction product was purified using column chromatography on silica-gel to afford the corresponding product with isolated yield up to 98%.

With the rapid development of chemical substances, we look forward to future research findings about 3430-17-9.

Reference:
Article; Taher, Abu; Lee, Dong-Jin; Lee, Ik-Mo; Rahman, Md. Lutfor; Sarker, Md Shaheen; Bulletin of the Korean Chemical Society; vol. 37; 9; (2016); p. 1478 – 1485;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59352-90-8, 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 59352-90-8 as follows.

The mixture of 5-bromo-6-methylpyridine-2,3-diamine (500.0 mg, 2.47 mmol) and diethyloxalate (3.0 mL) was stirred at 100° C. for 12 hours and then cooled to room temperature. Et2O was added to the reaction mixture to form a solid. The formed solid was then filtered and dried under reduced pressure to obtain light brown solid compound of 7-bromo-6-methylpyrido[2,3-b]pyrazine-2,3-diol (611.0 mg, 97percent). [1093] LCMS ESI (+): 256 (M+1), 258 (M+3) [1094] 1H-NMR (400 MHz, DMSO-d6); delta: 12.40 (s, 1H), 11.94 (s, 1H), 7.53 (s, 1H), 2.48 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59352-90-8, its application will become more common.

Reference:
Patent; C&C RESEARCH LABORATORIES; Ho, Pil Su; Yoon, Dong Oh; Han, Sun Young; Lee, Won Il; Kim, Jung Sook; Park, Woul Seong; Ahn, Sung Oh; Kim, Hye Jung; US2014/315888; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19621-92-2, 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. 19621-92-2, name is 6-Oxo-1,6-dihydropyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

Compound 1-193[00475] Compound 1-193 was synthesized as a yellow solid (33%) via the condensation of Compound 1-107 (1 equiv) with 6-hydroxypicolinic acid (3.0 equiv), HATU (2.5 equiv) and Hunig’s base (5 equiv) in acetonitrile at 45 C. Purification was carried out using Si02 chromatography employing a 0-40% (7:1 acetonitrile/MeOH)/DCM gradient following a DCM and sodium bicarbonate-based work-up.1H NMR (400 MHz, CD3OD) 8.85 (d, IH), 8.82-8.79 (m, 2H), 8.47 (s, IH), 8.02-7.98 (m, 2H), 7.62 (s, IH), 7.35-7.27 (m, IH), 7.14-7.06 (m, 2H), 7.05-6.95 (m, IH), 6.93 (d, IH), 6.04 (s, 2H) ppm. 1H NMR (400 MHz, CD3OD) 8.81 (d, IH), 8.45 (s, IH), 7.85-7.77 (m, IH), 7.77-7.40 (bs, IH), 7.55 (s, IH), 7.33-7.27 (m, IH), 7.13-7.05 (m, 2H), 6.98-6.93 (m, IH), 6.91 (d, IH), 6.91-6.86 (m, IH), 6.01 (s, 2H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19621-92-2, its application will become more common.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; KIM, Charles; NAKAI, Takashi; WAI-HO LEE, Thomas; MOORE, Joel; PERL, Nicholas, Robert; ROHDE, Jason; IYENGAR, Rajesh, R.; MERMERIAN, Ara; WO2012/3405; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951626-91-8, 5-Bromo-3-chloro-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, 951626-91-8, blongs to pyridine-derivatives compound. Recommanded Product: 951626-91-8

Step 1: 3-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine To a solution of 5-bromo-3-chloro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 4.32mmol) in 1,4-dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.32 g, 5.18 mmol), potassium acetate (1.27 g, 12.96 mmol) and l,l’-bis(diphenylphosphino)ferrocene- palladium(II)dichloride (315 mg, 0.43 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 2 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether ) affording 3-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- bjpyridine (770 mg, 64%): lU NMR (400 MHz, Chloroform-d) delta 11.61 (s, 1H), 8.76 (s, 1H), 8.45 (s, 1H), 7.33 (s, 1H), 1.40 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,951626-91-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89466-16-0 ,Some common heterocyclic compound, 89466-16-0, molecular formula is C6H7BrN2, 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.

To a solution of scheme 8-38 compound S1 (1 g, 3.89 mmol) and 6-bromo-3-methylpyridin-2-amine (870 mg, 4.67 mmol) in DCE (10 ml) was added DIPEA (2.56 mL, 15.56 mmol) and EEDQ (1.92 g, 7.78 mmol). The reaction was stirred at 90 C. overnight. The solvent was removed under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate=2:1) to afford compound 2 (710 mg, 43.0% yield) as a white solid. LC/MS (ESI) m/z: 426 (M+H)+.

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. 89466-16-0, 6-Bromo-3-methylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

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

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. 1374639-78-7, name is tert-Butyl 4-(6-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate, molecular formula is C28H38N8O3, 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. HPLC of Formula: C28H38N8O3

A solution of tert-butyl 4-(6-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3- d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-l-carboxylate (Ila) (50 g) in toluene (300 mL) was cooled to 10 C. Hydrochloric acid (6N, 100 mL) was added to the above solution in drop wise at 15 C. The reaction mass was stirred for 1 hour at 25-30 C. Hydrochloric acid (IN, 200 mL) was added to the above reaction mass at 25-30 C and stirred for 10 minutes at the same temperature. The reaction mass was then filtered and washed with toluene (1 x 50 mL) followed by hydrochloric acid (IN, 50 mL). Organic layer was separated and aqueous layer was cooled to 15 C. pH of aqueous layer was adjusted to pH=12.0-12.5 using saturated solution of sodium hydroxide (50% w/w) and stirred for 1 hour at 15-20 C. The resulted precipitate was then filtered, washed with water (3 chi 80 mL) and dried at 50 C for 6 hours to provide the title compound. (0169) Yield: 35.1 g; Purity by HPLC: 99.31 %

With the rapid development of chemical substances, we look forward to future research findings about 1374639-78-7.

Reference:
Patent; DR. REDDY?S LABORATORIES LIMITED; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; DAS GUPTA, Shirshendu; (39 pag.)WO2018/51280; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6313-54-8 ,Some common heterocyclic compound, 6313-54-8, molecular formula is C6H4ClNO2, 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.

Preparation 1; SYNTHESIS OF 2-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]ISONICOTINIC ACID METHYL ESTER; A. A mixture of 2-chloroisonicotinic acid (1.000 g, 6.340 mmol) and 5 drops of concentrated sulfuric acid in anhydrous methanol (50 mL) was refluxed for 3 hours. The reaction mixture was concentrated in vacuo, diluted with 20 mL of water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried and concentrated. The compound obtained was used for next step reaction without further purification. Yield 0.816 g, 75%.

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. 6313-54-8, 2-Chloroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XENON PHARMACEUTICALS INC.; US2008/167321; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem