Category: pyridine-derivatives

Electric Literature of 717843-56-6, 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. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine, molecular formula is C7H8BrNO, 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 172 (7bR,11aS)-N-(2-Methoxy-5-methyl-3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-6-amine A solution of tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4] oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)Carboxylate from Example 56, Part B (968 mg, 2.81 mmol), 3-bromo-2-methoxy-5-methylpyridine (515 mg, 2.55 mmol), and NaOt-Bu (404 mg, 4.20 mmol) in anhydrous toluene (40 mL) was stirred under an argon atmosphere in a sealable test tube. The mixture was degassed with argon at 85 C. for 30 min then cooled to 50 C. Tris(dibenzylideneacetone)dipalladium(0) (62 mg, 67 mumol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (84.0 mg, 135 mumol) were added; the reaction was sealed and heated at 85 C. for 16 h. The reaction was cooled to room temperature, diluted with EtOAc, filtered through a bilayer pad of diatomaceous earth and silica gel, and concentrated. Purification of the residue by flash column chromatography (silica gel, 10-50% EtOAc/hexanes) provided tert-butyl (7bR,11aS)-6-(2-methoxy-5-methyl-3-pyridinyl)amino-1,2,7b, 10,11,11 a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate (1.16 g, 89%). A solution of the intermediate in CH2Cl2 (20 mL) at -10 C. was treated with TFA (6 mL) and stirred for 1 h. Upon concentration in vacuo, the residue was partitioned between a 1:1 solution of CH2Cl2/satd NaHCO3 (100 mL). The aqueous phase was extracted with CH2Cl2 (4*75 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography [silica gel, 5-50% (80:18:2 CHCl3/MeOH/concd NH4OH)/CH2Cl2]and trituration with CH2Cl2/Et2O/hexanes provided the title compound of Example 172 (590 mg, 65%) as a tan solid: mp 122-124 C.; 1H NMR (300 MHz, CDCl3) delta 7.40 (s, 1H), 6.99 (s, 1H), 6.88 (s, 1H), 6.77 (s, 1H), 5.84 (br s, 1H), 4.75 (d, J=14.1 Hz, 1H), 4.58 (d, J=14.1 Hz, 1H), 4.3414.16 (m, 1H), 4.01 (s, 3H), 3.89-3.69 (m, 1H), 3.58-3.39 (m, 1H), 3.38-3.13 (m, 2H), 3.11-2.99 (m, 1H), 2.98-2.85 (m, 2H), 2.81-2.68 (m, 1H), 2.61-2.42 (m, 1H), 2.19 (s, 3H), 2.01-1.77 (m, 3H); ESI MS m/z 367 [C21H26N4O2+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 717843-56-6, 3-Bromo-2-methoxy-5-methylpyridine.

Reference:
Patent; Bristol-Myers Squibb Company; US6849619; (2005); B2;,
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. 56149-30-5, name is 2-Chloro-N-(4-methoxyphenyl)nicotinamide, the common compound, a new synthetic route is introduced below. Formula: C13H11ClN2O2

B. N-(4-Methoxyphenyl)-2-[1-(4-pyridyl)piperidin-4-yl-methyl]aminopyridine-3-carboxamide. A pressure tube (Aldrich) was charged with 2-chloro-N-(4-methoxyphenyl)pyridine-3-carboxamide (139 mg, 0.524 mmol), 1-(4-pyridyl)piperidine-4-methylamine (100 mg, 0.524 mmol), triethylamine (0.22 mL), and ethanol (3 mL). The mixture was placed in a 110 C. bath for 5 days. The mixture was concentrated and the residue purified by RPHPLC, yielding 52 mg (24%) of the title compound as a hydrochloride salt. 1NMR, IR; IS-MS, m/e 418 (m+1); Analysis for C25H26N5O2.2HCl: Calcd: C, 58.78; H, 5.96; N, 14.28; Found: C, 58.74; H, 5.90; N, 13.91.

The synthetic route of 56149-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6610704; (2003); B1;,
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. 55404-31-4, name is 3-Bromo-2-chloro-4-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. Quality Control of 3-Bromo-2-chloro-4-methylpyridine

(2) Synthesis of 3-bromo-2-methoxy-4-methylpyridine 3-bromo-2-chloro-4-methylpyridine (1 g) was added to DMF (5.6 mL). Sodium methoxide (28% solution in methanol, 4.6 mL) was added to the solution, and the mixture was stirred at 100 C. for 12 hours. The reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (1.1 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.40 (s, 3H), 4.00 (s, 3H), 6.77 (d, J=5.1 Hz, 1H), 7.94 (d, Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 55404-31-4.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); 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. 1124-29-4, name is 5-Acetylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Acetylpyridin-2(1H)-one

General procedure: To a solution of 111-3 (1 eq.) in DCM (0.1 mmol/mL) was added boronic acid III-4 (2 eq.), Cu(OAc)2 (1 eq), Pyridine (10 eq.) and Pyridine-N-Oxide (2 eq.), followed by addition of4A molecular sieve (quantity approx. equal to 111-3 ). The reaction mixture was stirred at rt underoxygen atmosphere overnight. After completion of the reaction indicated by TLC, the resultingmixture was filtered and washed with , the filtrate was washed with brine, dried over Na2SO4 andconcentrated. The residue was purified by column chromatography on silica gel to give 111-5.[0316] Compound 10 (61% yield): ?H NMR (DMSO-d6, 400 MHz) (5 8.43 (d, J = 2.4 Hz, 1H), 7.90 (dd, J= 9.6, 2.4 Hz, 1H), 7.39 (d, J= 8.8 Hz, 2H), 7.06 (d, J= 8.8 Hz, 2H), 6.51 (d, J = 9.6 Hz, 1H), 3.81 (s, 3H), 2.41 (s, 3H).

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, 1124-29-4, 5-Acetylpyridin-2(1H)-one.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, 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 73406-50-5.

To 3-hydroxypyridine-2-carboxylic acid (25 g, 179.5 mmol) in a 1 L dried flask was added 400 mL ethanol and 100 mL toluene followed by the addition of 10 mL sulfuric acid. The mixture was heated at reflux (95 C.) for 3 days. After cooling to rt, the mixture was concentrated to ¼ of its volume, and diluted with 600 mL ethyl acetate and 200 mL water. The aqueous layer was extracted with 200 mL ethyl acetate, and the combined organic layers were washed with sat NaHCO3 (3×200 mL), brine, and dried over Na2SO4. The solid was filtered off and the solvent was concentrated under reduced pressure to give 21.9 g of ethyl 3-hydroxypyridine-2-carboxylate (73%), which was used in the next step without purification. This ester (21.9 g, 131 mmol) was dissolved in pyridine and cooled to -40 C., followed by addition of trifluoromethanesulfonic anhydride (48 g, 170 mmol). The reaction mixture was then warmed to 0 C. for 30 min, and then warmed to rt for another 30 min. Water (100 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×200 mL), and the combined organic layers were washed with sat sodium bicarbonate (200 mL), water (200 mL), brine (200 mL), and dried over sodium sulfate. The solid was filtered off, and the solvent was removed under reduced pressure to give 39 g (99%) of desired product, which was used in the next step without further purification. 1H NMR (300 MHz, CD2Cl2) delta 8.73 (dd, 1H), 7.72 (dd, 1H), 7.62 (dd, 1H), 4.46 (q, 2H), 1.42 (t, 3H).

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. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US2005/192294; (2005); 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. 1227605-52-8, name is 2-Bromo-5-chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H3BrClNO

To a solution of 2,3-dibromo-5-chloropyridine (60 g, 221 mmol) in THF (500 mL) was added a solution of isopropylmagnesium chloride lithium chloride solution in THF (1 .3M, 185 mL) at -40 C over about 30 mm. The solution was stirred for 30 mm at -40 C and DMF (50 mL) was added. The resulting solution was warmed up to room temperature and stirred for 30 min. The reaction was quenched with 1 N HCl (400 mL) and MTBE (200 mL) was added. Organic layer was separated and washed twice with 5% aqueous NaHCO3 (200 mL). The solvent was removed under vacuum at 50 C. The resulting solids (aldehyde intermediate) were dissolved in methanol (400 mL). The solution was cooled to 5 C under an ice bath. NaBH4 (3.6 g) was added slowly over 30 min while maintaining the reaction temperature below room temperature. The reaction mixture was stirred for another 30 min followed by addition of water (125 mL). The resulting mixture was concentrated under vacuum to approximately 150 ml. Solids precipitated during the concentration. The suspension was stirred vigorously at room temperature for 1 h and solids were collected by filtration. The wet cake was dried in a vacuum oven over night at 60 C to give 52 (45.6 g, 93%) as a solid. 1H NMR (CDCl3, 400 MHz): oe 8.26 (d,J=2.5 Hz, 1H), 7.88 (d,J2.5 Hz, 1H), 4.73 (d,J 5.8 Hz, 2H), 2.33 (t,J= 11.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz): oe 147.12, 138.48, 138.39, 136.14, 132.06, 62.76.

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, 1227605-52-8, 2-Bromo-5-chloronicotinaldehyde.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHEN, Frank; MOLINARO, Carmela; WUELFING, W. Peter; YASUDA, Nobuyoshi; YIN, Jianguo; ZHONG, Yong-Li; LYNCH, Joseph; ANDREANI, Teresa; WO2013/169348; (2013); A1;,
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. 886371-28-4, name is 3-Bromo-6-chloroimidazo[1,2-a]pyridine. A new synthetic method of this compound is introduced below., Formula: C7H4BrClN2

To a solution of 3-bromo-6-chloro-imidazo[1,2-a]pyridine (1 eq, 18.1 mmol, 4.2 g), 2- chloropyridin-4-yl boronic acid (1.05 eq, 19 mmol, 3 g), Na2COs (2 eq, 36.2 mmol, 3.84 g) in dioxane (30 ml) and water (10 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (1.23 g). The reaction mixture is heated at 100 C for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgStheta4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound; [M+H]+ =264 (266).

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, 886371-28-4, 3-Bromo-6-chloroimidazo[1,2-a]pyridine.

Reference:
Patent; NOVARTIS AG; WO2009/50183; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 173528-92-2, 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. 173528-92-2, name is HMN-154. A new synthetic method of this compound is introduced below.

Example 1 (E)-4-[2-{2-[N-phenoxycarbonyl-N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl]pyridine 1.00 g of (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl ]pyridine was suspended in 40 ml of chloroform and, after adding 1.82 g of phenyl chlorocarbonate, 1.20 g of triethylamine was slowly added under ice cooling. Then, the mixture was stirred at room temperature for 5 minutes. The solvent was distilled off under reduced pressure and the desired product was purified by silica gel column (carrier:Wako Gel C200, developing solvent chloroform) to obtain the desired compound. The desired compound was treated with ethanol to obtain 0.71 g of a white granular crystal.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,173528-92-2, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1382335; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60186-15-4, 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. 60186-15-4, name is 2,4-Difluoro-5-nitropyridine, molecular formula is C5H2F2N2O2, 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.

To a solution of 2,4-difluoro-5-nitropyridine (335 mg, 2.093 mmol) in THF (10 mL) at – 40C, was added via cannula 2-methylmorpholine (80 mg, 0.791 mmol) dissolved in THF (1 mL) followed by Et3N (0.583 mL, 4.19 mmol). The cloudy yellow mixture was stirred at -40 C for 1 h and was allowed to warm to 0C. After stirring an additional 2 h, TLC (50% ethyl acetate in hexanes) showed a more polar spot with a small amount of starting material remaining. The mixture was concentrated. The product was purified by column chromatography on silica gel (20%? 50% ethyl acetate in hexanes; 25 g column) to afford 4-(2-fluoro-5-nitropyridin-4-yl)-2-methylmorpholine (264 mg, 1.094 mmol, 52% yield) as a yellow oil: NMR (400MHz, CDCh) delta 8.63 (s, 1H), 6.42 (s, 1H), 4.04 – 3.95 (m, 1H), 3.89 – 3.76 (m, 2H), 3.26 – 3.17 (m, 3H), 2.87 (dd, J=12.8, 10.0 Hz, 1H), 1.24 (d, J=6.3 Hz, 3H); 19 F NMR (376MHz, CDCh) delta -61.49 (s, IF); LC/MS (ESI) m/e 242.1 [(M+H)+, calcd for C10H13FN3O3 242.1].

According to the analysis of related databases, 60186-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (104 pag.)WO2018/98411; (2018); 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.53636-70-7, name is 6-Methyl-2,3-pyridinedicarboxylic acid, molecular formula is C8H7NO4, molecular weight is 181.1455, as common compound, the synthetic route is as follows.Quality Control of 6-Methyl-2,3-pyridinedicarboxylic acid

6-Methyl-2,3-pyridinedicarboxylic acid (10.0 g, 0. [055] mol) and [AC20] [(50] mL) were heated at [120 C] for 4 h, cooled, and concentrated to a brown oil. Isopropanol was added to the brown oil and the solution heated at [80 C] overnight. The volatiles were removed in vacuo and the residue gave, after washing with diethyl ether, 6- [METHYLPYRIDINE-2,] 3-dicarboxylic acid 2-isopropyl ester as a straw-coloured solid (8.8 g, [71%).-IH] NMR [(CDC13)] : 5 8.24 (d, [J=8.] 2, [1] H), 7.34 (d, [J=8.] 2,1 H), 5.34 [(SEP,] [J=6.] 2, [1 H),] 2.68 (s, 3 H), 1.39 (d, [J=6.] 2, [6 H).]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53636-70-7, 6-Methyl-2,3-pyridinedicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Prana Biotechnology Limited; WO2004/31161; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem