Pyridine-derivatives

Electric Literature of 1008-91-9, 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 1008-91-9 as follows.

General procedure: Piperazine derivatives 1-3 are known.10 Piperazine derivatives 4-14 were synthesized from the commercially available appropriate monoalkylated piperazines (1.44 mmol) and 2-nitro-1H-imidazolyl-propylbromide or 3-nitro-1H-1,2,4-triazolylpropylbromide (1.485 mmol)30 in the presence of potassium carbonate (13.24 mmol) in dry acetonitrile (25 mL) as described before.10 The reaction mixture was stirred under a nitrogen atmosphere at room temperature for 48 h, then filtered to remove the inorganic salts. The organic filtrate was evaporated and the residue extracted from water-chloroform. The organic layer was separated and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated and the residue purified by preparative TLC on alumina plates with ethyl acetate:petroleum ether mixture. The desired product was dissolved in ethyl acetate and converted to its HCl salt by treating with HCl gas in dry ether (1 M solution)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1008-91-9, its application will become more common.

Reference:
Article; Papadopoulou, Maria V.; Bloomer, William D.; Rosenzweig, Howard S.; Kaiser, Marcel; Chatelain, Eric; Ioset, Jean-Robert; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6600 – 6607;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, 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, 5349-17-7, blongs to pyridine-derivatives compound. COA of Formula: C7H7Br2NO

(c) Preparation of [(2-chloro-6-nitrophenyl)methyl](4-(4-pyridyl)(1,3-thiazol-2-yl))amine.To a solution of N-({[(2-chloro-6-nitrophenyl)methyl]amino}thioxomethyl)benzamide (Step b) (1.22 g, 3.5 mmol) in 70% aqueous MeOH (50 ML) was added K2CO3 (567 mg, 4.1 mmol) and the reaction was heated to reflux.After 1.5 h, the reaction was cooled (40 C.) and 2-bromo-1-(4-pyridyl)ethan-1-one hydrobromide (992.4 mg, 3.5 mmol) was added.After 1.5 h, the reaction mixture was cooled to RT and purified by flash chromatography with hexanes:EtOAc:CH2Cl2:MeOH (9:1:0:0, 3:1:0:0, 1:1:0:0, 0:0:49:1) as eluant to afford an off-white amorphous solid. MS m/z: 347 (M+1); 345 (M-1). Calc’d for C15H11ClN4O2S-b 346.03.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5349-17-7, its application will become more common.

Reference:
Patent; Huang, Qi; Kaller, Matthew; Nguyen, Thomas; Norman, Mark H.; Rzasa, Robert; Wang, Hui-Ling; Zhong, Wenge; US2003/229068; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6200-60-8, Adding some certain compound to certain chemical reactions, such as: 6200-60-8, name is Imidazo[1,2-a]pyridine-3-carboxylic acid,molecular formula is C8H6N2O2, 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 6200-60-8.

To a solution of imidazo[1,2-a] pyridine-3-carboxylic acid (250 mg) in DMF (7 mL), EDCI (443 mg, 1.5 equiv.), HOBt (312 mg, 1.5 equiv.), DIPEA (805 muL, 3.0 equiv.) and compound 73 (404 mg, 1.0 equiv.) were added. The resulting mixture was stirred at R.T. overnight. The reaction mixture was diluted with AcOEt (15 mL), washed with HCl 1M (2*10 mL) and water (2*10 mL). Combined aqueous layers were saturated with NaHCO3 and extracted with AcOEt (2*10 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash-chromatography (MeOH 2% to 5% in CH2Cl2) followed by preparative HPLC afforded the product as a white solid (9.3 mg, yield <5%). 1H-NMR (400 MHz, DMSO): 1.11-1.79 (m, 13H, 5*CH2 + CH3); 3.33 (q, J 7.0 Hz, 2H, N-CH2); 6.81 (dd, J 1.9 Hz, J 8.1 Hz, 1H, Ar); 6.90 (d, J 2.0 Hz, 1H, Ar); 7.20 (m, 1H, Ar); 7.55 (m, 1H, Ar); 7.75-7.78 (m, 2H, Ar); 8.56 (s, 1H, Ar); 9.36 (bs, 1H, NH); 9.47 (m, 1H, Ar). N-CH signal under water peak. M/Z (M+H)+ = 407. 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. 6200-60-8, Imidazo[1,2-a]pyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Domain Therapeutics; EP2210891; (2010); 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. 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Chloro-3-nitropyridin-2-amine

2-Amino-3-nitro-4-chloropyridine (967 mg, 5.59 mmol) was dissolved in isopropanol (20 mL) and DIPEA (1.85 mL, 11.18 mmol) was added followed by N-methylpiperazine (0.744) mL, 6.71 mmol). The mixture was reacted at 90 C. for 12 h. A large amount of gold solid was isolated by cooling and was filtered, washed with isopropyl alcohol and ether in that order, and dried in vacuo to give the title compound (1.21 g, yield 92%) as a golden yellow solid.

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, 6980-08-1, 4-Chloro-3-nitropyridin-2-amine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Cao Bin; (103 pag.)CN103570683; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1123194-98-8 ,Some common heterocyclic compound, 1123194-98-8, molecular formula is C10H10BrN3O, 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.

Synthesis of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide Triethylamine (52 ml) was added to a suspension of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (49.8 g), tris(dibenzylideneacetone)dipalladium (0) (5.11 g), tri-o-tolylphosphine (3.41 g) and acrylamide (14.5 g) in N,N-dimethyl formamide (260 ml). The reaction solution was stirred at 100C for 50 minutes. The reaction solution was returned to room temperature and then filtered through celite. The filter cake was sequentially washed with N,N-dimethylformamide, methanol, a 50% N,N-dimethylformamide solution and N,N-dimethylformamide. The resulting filtrate was filtered through celite again, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the reaction solution was concentrated again. Toluene and a saturated sodium bicarbonate solution were added to the resulting residue, and the insoluble matter was collected by filtration. The resulting powder was dried under reduced pressure to obtain 42.96 g of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 2.30 (d, J=0.8Hz, 3H), 4.07 (s, 3H), 5.57 (brs, 1H), 5.68 (brs, 1H), 6.98 (brs, 1H), 7.00 (d, J=15.2Hz, 1H), 7.06 (d, J=7.6Hz, 1H), 7.54 (d, J=7.6Hz, 1H), 7.56 (d, J=15.2Hz, 1H), 7.82 (d, J=1.2Hz, 1H). ESI-MS; m/z 259 [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. 1123194-98-8, 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-90-2, 3,4-Dibromopyridine, 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, 13534-90-2, blongs to pyridine-derivatives compound. Computed Properties of C5H3Br2N

The titled compound was prepared by the reaction of 3,4-dibromopyridine (1.01 g, 4.26 mmol) with 4-nitrophenylboronic acid pinacol ester (1.06 g, 4.26 mmol) using cesium carbonate (2.07 g, 6.39 mmol) and [l, -bis(diphenylphosphino)ferrocene]dichloropalladium (II) (155 mg, 0.21 mmol) in a mixture of DMSO and water (20 mL, 3: 1) as per the procedure described in Step 1 of Intermediate 1 to yield 455 mg of the product; 1H NMR (300 MHz, CDC13) delta 7.33 (d, 7 = 4.8 Hz, 1H), 7.63 (d, 7 = 8.7 Hz, 2H), 8.35 (d, 7 = 8.7 Hz, 2H), 8.64 (d, 7 = 5.1 Hz, 1H), 8.89 (s, 1H) ; ESI-MS (m/z) 281 (M+2H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13534-90-2, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; SHELKE, Sandeep Yadunath; PARDESHI, Shailesh Ramesh; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (181 pag.)WO2017/21879; (2017); 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.175965-83-0, name is 2-Fluoro-4-methoxypyridine, molecular formula is C6H6FNO, molecular weight is 127.12, as common compound, the synthetic route is as follows.name: 2-Fluoro-4-methoxypyridine

Method Z Step l To a solution of F6 (40.0 mg, 0.098 mmol) and 2-fiuoro-4-methoxypyridine (25.0 mg, 0.197 mmol) in DMSO (2 mL) was added Cs2C03 (96.0 mg, 0.295 mmol). The mixture was stirred at 1 10 C for 1 h under microwave condition, and then quenched with water, extracted with EtOAc (25 mL x 4). The combined extracts were washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was further purified by p-HPLC (TFA) to give Example 71.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175965-83-0, 2-Fluoro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; CUMMING, Jared, N.; LIU, Hong; SCOTT, Jack, D.; (0 pag.)WO2016/85780; (2016); 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. 104408-24-4, name is 6-Hydrazinylnicotinonitrile, molecular formula is C6H6N4, 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 6-Hydrazinylnicotinonitrile

General procedure: To a solution of 2-hydrazinylpyridine (2, 0.5?mmol) in EtOH (5?mL) was added the corresponding isothiocyanate (3, 0.6?mmol) slowly at room temperature. After the total consumption of the substrate 2 (indicated by TLC), the reaction mixture was treated with iodine (140?mg, 0.55?mmol) and K2CO3 (138?mg, 1?mmol) in sequence, and then stirred at room temperature until TLC indicated the disappearance of the addition intermediate 4. Upon the completion of the reaction, it was quenched with 5% Na2S2O3 (5?mL), diluted with brine (10?mL) and then extracted with CH2Cl2 (enriched 5% MeOH, 4?*?10?mL). The combined organic layer was dried over anhydrous Na2SO4, concentrated, and then purified through silica gel column chromatography using a mixture of EtOAc/petroleum ether (PE) or MeOH/EtOAc as the eluent to afford the product 1.

With the rapid development of chemical substances, we look forward to future research findings about 104408-24-4.

Reference:
Article; Jiao, Shufeng; Wang, Zhen; Zhao, Qiongli; Yu, Wenquan; Chang, Junbiao; Tetrahedron; vol. 74; 24; (2018); p. 3069 – 3073;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52718-95-3, Adding some certain compound to certain chemical reactions, such as: 52718-95-3, name is Methyl 2-bromonicotinate,molecular formula is C7H6BrNO2, 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 52718-95-3.

Intermediate [1-B] (1.5 eq), methyl-2-bromoicotinate (1.1 eq), CuI (0.03 g), K2CO3 (2.0 eq), and L-Proline (0.04 eq) were dissolved in toluene (0.1 M) and stirred at a temperature of 130 i for 12 hours. After the reaction mixture was cooled to room temperature, and an organic layer was dried by using magnesium sulfate and concentrate, and column chromatography was used to obtain Intermediate [1-C] (yield: 59%).

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. 52718-95-3, Methyl 2-bromonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samsung Display Co., Ltd.; KANG, Sunwoo; JEON, Sangho; CHO, Youngmi; (80 pag.)US2020/168817; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 614750-81-1, 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. 614750-81-1, name is [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde. A new synthetic method of this compound is introduced below.

(b) 1-(6-Methyl-pyridin-2-yl)-2-[1,2,4]triazolo[1,5-a]pyridin-6-yl-ethanone To a solution of [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde (3 g, 20 mmol; see subpart (a) above) and [(6-methyl-pyridin-2-yl)-phenylamino-methyl]-phosphonic acid diphenyl ester (8.8 g, 20 mmol; prepared from 6-methyl-pyridine-2-carboxaldehyde (Aldrich-Sigma, St. Louis, Mo.) according to Tetrahedron Lett. 39:1717-1720 (1998)) in a mixture of THF (40 mL) and iPrOH (10 mL) was added Cs2CO3 (8.6 g, 26 mmol) and the mixture was stirred at room temperature for overnight. A solution of 3N HCl (30 mL) was added dropwise to the above mixture and stirred for 1 hour. It was then diluted with MTBE (methyl t-butyl ether) and extracted with 1N HCl twice. The aqueous extracts were neutralized with ca. 50percent KOH until pH 7-8 was reached and precipitates formed. The precipitates were collected, washed with water, and dried to yield 1-(6-methyl-pyridin-2-yl)-2-[1,2,4]triazolo[1,5-a]pyridin-6-yl-ethanone as an off white solid (2.9 g). The filtrates were extracted with EtOAc and dried over MgSO4 and concentrated. The residue was recrystallized with iPrOH/H2O to yield more desired product (0.6 g). ESP+, m/e 253. 1H NMR (CDCl3, 300 MHz), delta 8.6 (s, 1H), 8.29 (s, 1H), 7.87 (d, 1H), 7.72 (t, 1H), 7.70 (d, 1H), 7.53 (dd, 1H), 7.36 (d, 1H), 4.61 (s, 2H), 2.66 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,614750-81-1, [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Lee, Wen-Cherng; Sun, Lihong; Shan, Feng; Chuaqui, Claudio; Zheng, Zhongli; Petter, Russell C; US2006/63809; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem