Category: pyridine-derivatives

Synthetic Route of 15128-82-2 ,Some common heterocyclic compound, 15128-82-2, molecular formula is C5H4N2O3, 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.

(S)-1-(2,6-dichloro-3-fluorophenyl)ethanol (20.9 g, 0.10 mol) was dissolved in 200 mL anhydrous tetrahydofuran, to which 3-hydroxy-2-nitropyridine (16.0 g, 0.11 mol) and triphenylphosphine (40.0 g, 0.15 mol) were sequentially added under a nitrogen atmosphere, and the reaction solution was stirred at room temperature for 1 hour, cooled to 0 C. and diisopropyl azodicarboxylate (40 mL, 0.15 mol) was added dropwise. After the addition was complete, stirring was continued at 0 C. for 12 hours. The solvent was distilled off to obtain an oily material, which was separated by silica gel column chromatography, to give (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (20.2 g). Yield: 61%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15128-82-2, its application will become more common.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; LIANYUNGANG RUNZHONG PHARMACEUTICAL CO., LTD.; CENTAURUS BIOPHARMA CO., LTD.; GONG, Feng; LI, Xinlu; ZHAO, Rui; ZHANG, Xiquan; XU, Xinhe; LIU, Xijie; XIAO, Dengming; HAN, Yongxin; (22 pag.)US2018/244649; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 186593-43-1, Adding some certain compound to certain chemical reactions, such as: 186593-43-1, name is 5-Amino-3-bromo-2-methylpyridine,molecular formula is C6H7BrN2, 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 186593-43-1.

General procedure: 1.2.2.1. General method Bl To a stirred solution of Intermediate Gen-1 (1 to 1.2 eq.), and amine derivative (1 eq.) in DCM or DMF are added TBTU or HATU (1 to 1.2 eq.) followed by TEA or NMM (2 to 3 eq.) at room temperature under argon, the reaction mixture is stirred at room temperature until completion. Then the reaction is quenched with water, the layers are separated. The organic layer is dried over Na2SO i, filtered and evaporated to dryness. Alternatively, the reaction is concentrated in vacuo, the residue is partionned between EtOAc or a mixture of EtOAc/nBuOH and a saturated aqueous NH4C1 solution or water. The layers are separated, the organic layer is dried over Na2S04, filtered and evaporated to dryness. Then the residue is purified by chromatography on silica gel to afford the expected Intermediate.

According to the analysis of related databases, 186593-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; SANIERE, Laurent Raymond Maurice; HUCK, Jacques; DYKES, Graeme James; SCHMITT, Benoit Antoine; BLANC, Javier; BUTLER, Anna Sara; BEAUMONT, Stephane Nicolas Alain; BONNATERRE, Florence Marie-Emilie; WO2015/24905; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 500-22-1, 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 500-22-1 as follows.

General procedure: In a round-bottomed flask equipped with a condenser and a magnetic stirrer, a mixture of aldehyde (1 mmol), 1,2-phenylenediamine (1 mmol) and Cu(II)-TDnSiO2 (10 mg, containing 0.0034 mmol Cu(II)) in EtOAc (2 mL) was stirred at 50 C. The progress of the reaction was monitored by TLC (eluent: n-hexane/EtOAc, 2:1). After completion of the reaction, the mixture was cooled to room temperature and EtOAc/EtOH (3:2, 15 mL) was added. The catalyst was separated by filtration and washed with EtOAc (10 mL). The filtrate was evaporated and the crude product was purified by recrystallization from EtOAc or EtOH to afford the pure product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,500-22-1, its application will become more common.

Reference:
Article; Nasr-Esfahani, Mahboobeh; Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad Reza; Moghadam, Majid; Mirkhani, Valiollah; Tangestaninejad, Shahram; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 243 – 254;,
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Pyridine | C5H5N – PubChem

Electric Literature of 1620-77-5, 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.1620-77-5, name is 5-Methylpicolinonitrile, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.

[5-METHYL-PYRIDINE-2-CARBONITRILE] (3.34 g, 28.3 mmol) was mixed with [18] percent HCl (12 ml) and ethanol [(6ML)] and refluxed for 40 h. The reaction mixture was concentrated by rotavapor and the residue was triturated with acetone to give off-white solid 5-methyl-pyridine-2- carboxylic acid hydrochloride. This solid was hydrogenated with [PT02] in ethanol for 2 days until no W active material left. The reaction mixture was filtered, concentrated by vacuum. The residue was triturated with acetone to give 5.3 g of cis and trans 5-methyl- piperidine-2-carboxylic acid hydrochloride as white solid (quantitative).

Statistics shows that 1620-77-5 is playing an increasingly important role. we look forward to future research findings about 5-Methylpicolinonitrile.

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

Adding a certain compound to certain chemical reactions, such as: 76469-41-5, 2,3,5-Trifluoropyridine, 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, 76469-41-5, blongs to pyridine-derivatives compound. Formula: C5H2F3N

A mixture of 2, 3, 5-trifluoropyridine (5.0 g, 37.6 mmol, 1.0 equiv) and 1, 3-dimethyl propanedioate (7.4 g, 56.0 mmol, 1.5 equiv) and Cs 2CO 3 (24.5 g, 75.2 mmol, 2.0 equiv) in DMSO (100.0 mL) was stirred for 10 hours at 100C under nitrogen atmosphere. The resulting mixture was extracted with EtOAc (4 x 50 mL). The combined organic layers were washed with H2O (3 x 50 mL), dried over anhydrous Na 2SO 4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (20: 1) to afford 1, 3-dimethyl 2- (3, 5-difluoropyridin-2-yl) propanedioate (8.1 g, 79.13%) as a yellow oil. LCMS: m/z (ESI), [M+H] + = 246.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76469-41-5, its application will become more common.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; ZENG, Qingbei; QI, Changhe; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (206 pag.)WO2020/52631; (2020); 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.1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid, molecular formula is C6H3BrFNO2, molecular weight is 219.9959, as common compound, the synthetic route is as follows.Recommanded Product: 1052714-46-1

[0273] 6-Bromo-5-fluoro-pyridine-2-carboxylic acid (24.0 g, 109 mmol) was dissolved in a mixture of EtOH (400mL) and cone. H2SO4 (17.5 mL, 328 mmol). The mixture was heated at 90 C for 2.5 h. After cooling to 0 C, a solution of 3.50 M NaOH (90.0 mL, 315 mmol) was slowly added with vigorous stirring (pH adjusted to approx. 4), followed by a sat. solution of NaHC03 until pH was approx. 8. The slurry was filtered through a pad of Celite, and the filtrate was concentrated under reduced pressure. The residue was suspended in cold water (300 mL) and stirred at 0 C for 5 m. The mixture was filtered, washing with water, and the solid was dried under vacuum to provide the title compound as a solid (20.4 g, 75%). XH NMR (500 MHz, (0777) CDC13) delta 8.12 (dd, J = 8.3, 3.6 Hz, 1H), 7.53 (dd, J = 8.3, 7.0 Hz, 1H), 4.47 (q, J = 7.1 Hz, 2H), 1.43 (t, J = 7.1 Hz, 3H). LC-MS (Method C): m/z (ES+), [M+H]+ = 247.8. HPLC tR = 1.74 m.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1052714-46-1, 6-Bromo-5-fluoropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; CUMMING, John, Graham; WU, Frank, Xinhe; EDMAN, Karl, Henrik; CHEN, Hongming; BROWN, Dean, Gordon; BURLI, Roland, Werner; JOHNSTONE, Shawn, Donald; BROWN, Giles, Albert; TEHAN, Benjamin, Gerald; TEOBALD, Barry, John; CONGREVE, Miles, Stuart; (187 pag.)WO2017/194716; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 571189-16-7, 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 571189-16-7, name is tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2 tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate In a nitrogen atmosphere, to a solution of tert-butyl 4-(6-nitro-3-pyridine) piperazine-1-carboxylate (28.00 g, 90.81 mmol, 1.00 equivalent) in methanol (600 mL) was added palladium on carbon (6%, 1.7 g). The suspension was evacuated and filled with hydrogen several times. The solution was stirred at 50C in a hydrogen atmosphere (50psi) for 18 hours. TLC (dichloromethane: methanol = 10: 1) showed that the starting material reacted completely. The suspension was filtered, and the filtrate was dried using a rotary vacuum dryer to give the title compound (24.13 g, 86.69 mmol. 95.46% yield) as a purple solid. 1H NMR (400 MHz, CDCl3) delta 7.78 (d, J = 2.64 Hz, 1H) 7.18 (dd, J = 8.78, 2.89 Hz, 1H) 6.50 (d, J = 8.78 Hz, 1H) 4.21 (brs, 2H) 3.60-3.54 (m, 4H) 3.00-2.92 (m, 4H) 1.48 (s, 9H).

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 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; DING, Charles Z.; CHEN, Shuhui; ZHAO, Baoping; XU, Zhaobing; LIU, Yingchun; LIN, Ruibin; WANG, Fei; LI, Jian; (101 pag.)EP3269715; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 199522-66-2, 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. 199522-66-2, name is N1-(5-Bromopyrid-2-yl)ethane-1,2-diamine, molecular formula is C7H10BrN3, 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.

Step 2: 3-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-3H-quinazolin-4-one (compound 75) A suspension of primary amine 73 (1.17 g, 5.40 mmol) and isatoic anhydride 74 (880 mg, 5.40 mmol) in methanol (25 mL) was stirred for 3 h at 50 C. and then concentrated. The resulting oily residue was dissolved in 88% formic acid (20 mL) and refluxed overnight. After removal of formic acid, the solid residue was purified through column chromatography on silica gel (5% methanol in dichloromethane) to give 1.24 g (3.6 mmol, 67% yield) of 75. 13C NMR (300 MHz, CDCl3): 161.6, 156.8, 147.7, 147.6, 147.2, 139.8, 134.5, 127.4, 126.8, 126.3, 121.6, 110.1, 107.0, 46.3, 40.1. LRMS=347.1 (M+1).

According to the analysis of related databases, 199522-66-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MethylGene, Inc.; US2005/288282; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55314-16-4, 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.55314-16-4, name is 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one, molecular formula is C10H12N2O, molecular weight is 176.2151, as common compound, the synthetic route is as follows.

The starting material was added 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (Compound 4) (1.76 g, 0.01 mol) in a three-neck flask.Guanidine hydrochloride (2.87 g, 0.03 mol)And sodium hydroxide (1.2g, 0.03mol), add 25ml of solvent t-butanol, stir, heated in a constant temperature oil bath to 85 C reflux reaction, 6-8h. After the reaction is completed, the solvent is spin-dried, an appropriate amount of water and ethyl acetate are added, the insoluble solid is filtered, and the filter cake is washed with water and dried to obtain a yellow solid; the filtrate is further subjected to extraction, the organic phase is collected, dried, and the solvent is dried and dried. The solid was subjected to column chromatography to give a pale yellow solid, Compound 5 (1.55 g, yield: 90%).

Statistics shows that 55314-16-4 is playing an increasingly important role. we look forward to future research findings about 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one.

Reference:
Patent; Southeast University; Cai Jin; Ning Yao; Ji Min; Wang Yingying; Huang Mingqi; (20 pag.)CN110078708; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1093880-37-5, Adding some certain compound to certain chemical reactions, such as: 1093880-37-5, name is 6-Chloro-2-fluoronicotinaldehyde,molecular formula is C6H3ClFNO, 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 1093880-37-5.

Example 112A methyl 3 -(3 -(6-chloro-2-fluoropyridin-3 -yl)-3 -hydroxypropanoyl)benzoate A solution of methyl 3-acetylbenzoate (1 g, 5.61 mmol) in tetrahydrofuran (25 mL) was cooled to – 78 C, treated dropwise with 1 M lithium bis(trimethylsilyl)amide in tetrahydrofuran (7.30 ml, 7.30 mmol), stirred at – 78 C for 15 minutes, treated dropwise with a solution of 6- chloro-2-fluoronicotinaldehyde (0.895 g, 5.61 mmol) in tetrahydrofuran (10 mL), stirred at -78 C for 15 minutes, treated with saturated NH4C1 solution (30 mL) and the mixture was allowed to warm to near room temperature. The mixture was extracted with ethyl acetate (30 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layers were washed with brine, dried (MgS04), filtered, and concentrated. The residue was chromatographed on silica gel and eluted with a gradient of 20 % – 100 % ethyl acetate in heptanes to provide the title compound (1.35 g, 4.00 mmol, 71.2 % yield). 1H NMR (400 MHz, CDCl3) 5 ppm 8.56 (t, J = 1.8 Hz, 1H), 8.28 (dt, J= 7.7, 1.5 Hz, 1H), 8.15 (dt, J = 7.9, 1.6 Hz, 1H), 8.10 – 8.05 (m, 1H), 7.59 (t, J = 7.8 Hz, 1H), 7.30 (dd, J= 7.8, 1.0 Hz, 1H), 5.53 (dt, J= 9.4, 2.9 Hz, 1H), 3.96 (s, 3H), 3.89 (d, J= 3.9 Hz, 1H), 3.55 (dd, J= 18.0, 2.4 Hz, 1H), 3.29 (dd, J= 18.0, 9.3 Hz, 1H); MS (ESI) m/z 338 (M+H)+.

According to the analysis of related databases, 1093880-37-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; KYM, Philip, R.; WANG, Xueqing; SEARLE, Xenia, B.; LIU, Bo; YEUNG, Ming, C.; ALTENBACH, Robert, J.; VOIGHT, Eric; BOGDAN, Andrew; KOENIG, John, R.; (332 pag.)WO2016/69757; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem