Category: pyridine-derivatives

Application of 18605-16-8 , The common heterocyclic compound, 18605-16-8, name is 6-Fluoro-2-methyl-3-nitropyridine, molecular formula is C6H5FN2O2, 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.

N-(2-Methyl-6-morpholin-4-ylpyridin-3-yl)guanidine; Step 1 : 4-(6-Methyl-5-nitropyridin-2-yl) morpholine; To a solution of 2-fluoro-5-nitro-6-picoline (3.0 g, 19.2 mmol) in DMSO (26 mL) were added morpholine (3.35 mL, 38.4 mmol) and potassium carbonate (6.64 g, 48.0 mmol). The reaction mixture was allowed to stir overnight, at 70C. The reaction mixture was then partitioned between EtOAc (40 mL) and water (40 mL). The organic solution was separated and the aqueous solution was extracted with EtOAc (2 x 40 mL). The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated to give 4-(6-methyl-5-nitropyridin-2-yl) morpholine (4.0 g, 99%), as a muddy green solid. LCMS (FA): Rt = 1.59 min, m/? = 224.0 (M+H).

The synthetic route of 18605-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu, T.; DUFFEY, Matthew, O.; ELDER, Amy, M.; GUO, Jianping; LI, Gang; REYNOLDS, Dominic; SOUCY, Francois; VOS, Tricia, J.; WO2010/65134; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59237-53-5, 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 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A flask was charged with methyl-6-chloro-5-nitronicotinate (2.00 g, 9.23 mmol), PdC12(PPh3)2 (324.00 mg, 461.70 jimol) and Cul (87.90 mg, 461.70 jimol). The system was evacuated and filled thrice with N2 before addition of TEA (44 mL) and DMF (88 mL) and the resulting solution was degassed with N2 for 10 mm. Thencyclopropylacetylene (1 .56 mL, 18.49 mmol) was added and the reaction mixture was stirred at rt for 18 h. Then, the reaction mixture was concentrated. The residue was purified by column chromatography on silica gel (Irregular SiOH 15-40 jim, 80 g, dry loading on celite®, mobile phase: heptane/DCM, gradient from 50:50 to 0:100). The fractions containing the product were combined and concentrated under vacuum to give1.3 g of intermediate 293 (58percent yield, brown solid).

According to the analysis of related databases, 59237-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15862-37-0, 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 15862-37-0, name is 2,5-Dibromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 5-Bromo-2-(4-chloro-3,5-difluorophenyl)-3-nitropyridine A 24/40-100 mL round bottom flask was charged with 2,5-dibromo-3-nitropyridine (2.00 g, 7.09 mmol) and 2-(4-chloro-3 ,5 -difluorophenyl)-4,4,5 ,5 -tetramethyl-1,3,2-dioxaborolane (1.95 g, 7.09 mmol). The mixture was diluted with THF(30 mL), and PdC12(dppf) (0.0520 g, 0.07 10 mmol) was added followed by aq. potassiumphosphate tribasic, (2.0 M, 7.09 mL, 14.2 mmol). The vial was sealed and degassed usingultra pure argon and sonication for 2 mm. The vial was placed in an oil bath preheated to65 C. After 35 mm, the reaction mixture was concentrated under reduced pressure,diluted with ethyl acetate and a brine solution, and filtered through a pad of Celite. The contents of the flask were transferred into a separatory funnel, and the organic was washed with brine (3X) and then back extracted with ethyl acetate. The combined organics were dried with magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (40 g ISCO RediSep Rf, loaded inlwith:DCM and dried, initial waste: 0 mL, fraction size: 9 mL 13x 100 mm, and eluted with dichloromethane in hexanes 0% [102 mL], 0-20% [150 mL], 20% [501 mL], 20-50% [252 mL], 50% [150 mL]). The fractions were collected to give 1.59 g (64%). ?H NMR (400MHz, CDC13) oe 8.94 (d, J=2.0 Hz, 1H), 8.37 (d, J=2.3 Hz, 1H), 7.23-7.16 (m, 2H). Mass found 350 [M+H].

According to the analysis of related databases, 15862-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 626-64-2 , The common heterocyclic compound, 626-64-2, name is Pyridin-4-ol, molecular formula is C5H5NO, 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.

4-Hydroxy pyridine (0.68g, 7.20mmol), 3,5-difluorobenzonitrile (0.5g, 3.60mmol), K2CO3 (1.73g, 12.6mmol) and DMF (15ml) were taken in a 50ml round bottom flask. The mixture was stirred constantly at 80C (Scheme 1). After 48h, heating was stopped and the reaction mixture was allowed to cool down at room temperature. After that, the mixture was poured into ice-cold water to obtain a white solid precipitate. It was filtered and air dried. Yield: 0.96g, (92%). SI-MS: [M+H], m/z: 290.0934 (100%) (calcd for C17H11N3O2, 289.0851) (Fig. S1). Anal. calcd. for C17H11N3O2: C, 70.59; H, 3.80; N, 14.53%. Found: C, 70.61; H, 3.82; N, 14.6% IR (cm-1, KBr pellet): 3426 (m), 3044 (m), 2943 (m) 2245 (m), 1651 (s), 1599 (s), 1443 (s), 1349 (s), 1248 (s), 1199 (s), 1090 (m), 892 (m), 843 (s), 690 (m), 557(m), 496 (m) (Fig. S2).

The synthetic route of 626-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agarwal, Rashmi A.; De, Dinesh; Polyhedron; vol. 185; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89809-64-3, 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. 89809-64-3, name is 5-Chloropicolinonitrile, molecular formula is C6H3ClN2, 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.

A. Preparation of methyl 5-chloropicolinate A mixture of 5-chloropicolinonitrile (4 g, 28.87 mmol), concentrated aq. HCl (10 mL) and concentrated H2SO4 (5 mL) in methanol (30 mL) was stirred at reflux for 35 h under argon. The reaction mixture was concentrated and then carefully diluted with water (50 mL). The pH was adjusted to 6-7 with 20% aqueous NaOH solution. The product was extracted with EtOAc (3*20 mL). The combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated under vacuum to obtain 4.9 g of the title compound as a white solid. HPLC/MS: retention time=1.977 min, [M+H]+=172.

According to the analysis of related databases, 89809-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 99163-12-9, 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. 99163-12-9, name is 4-Pyridin-4-yl-benzaldehyde. A new synthetic method of this compound is introduced below.

Having established an access to both hexT-pyrazolines, and hexT- pyrazoles by selection of reaction conditions, next libraries of both heterocycles from aldehydes, a hydrazide, and hexT-4 were synthesized (Figure 28). While aldehydes are abundantly available to introduce diversity in the heterocycle, the hydrazide had to be synthesized de novo, and therefore lent itself to functionalization with an acylatable primary amine 11 for combinatorial library synthesis. In the course of the library synthesis it was found that aliphatic aldehydes related to isobutyric aldehyde AJ, i.e. branched in a-position, neatly yielded the pyrazoline conjugates hexT-12 in MeCN at 50C (condition A, Table 27) whereas linear aliphatic and benzaldehydes were not reactive (Figure 29). Only a small number of benzaldehydes furnished the pyrazolines hexT- 12 in glacial acetic acid at 50C (Figure 25). However, both branched aliphatic aldehydes, and benzaldehydes yielded pyrazoles hexT-13 (Figure 30) in glacial acetic acid at 60C (condition C, Figure 27). Notably, isatin L gave rise to the spirooxindole hexT-13L under these conditions. Linear aliphatic aldehydes were again not reactive, also pyridine carboxaldehydes and related structures did not yield the corresponding hexT-13 conjugates, likely due to poisoning of the catalyst. In total 23 pyrazolines hexT-12 and 41 pyrazoles hexT-13 were obtained with yields between 0.5 and 3 nmol after purification by HPLC. Usually, branched aliphatic aldehydes gave higher yields than aromatic aldehydes. The pyrazolines hexT-12 and pyrazoles hexT-13 were ligated with each a duplex DNA encoding the heterocycles, and dsDNA sequences encoding the aldehyde building blocks.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,99163-12-9, 4-Pyridin-4-yl-benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; TECHNISCHE UNIVERSITAeT DORTMUND; BRUNSCHWEIGER, Andreas; KRAUSE, Norbert; ANTONCHICK, Andrey; KLIKA SKOPIC, Mateja; SALAMON, Hazem; BUGAIN, Olivia; JUNG, Kathrin; WAGNER, Bernd; (72 pag.)WO2017/108741; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 97483-77-7, 5-Bromopicolinonitrile, 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, Application In Synthesis of 5-Bromopicolinonitrile, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Bromopicolinonitrile

Part A: Compound 414 (1.0 g, 5.46 mmol) was suspended in diethylether (30 mL) and cooled to -78 0C. Titanium (IV) isopropoxide (1.7 mL, 6.01 mmol) was added dropwise and stirred for 5 minutes. Ethyl magnesium bromide (3M in diethylether, 4.0 mL) was added dropwise and stirred for 30 minutes at the same temperature and 1 hour at room temperature. Boron trifluoride dietherate (1.55 g, 10.92 mmol) was added dropwise and the reaction was stirred for 2 hours. The reaction was quenched with 1 M hydrochloric acid and the aqueous layer was washed with diethyl ether. The aqueous layer was made basic (pH = 10) and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. Column chromatography (1 :1 hexanes/ethyl acetate) provided the desired product (350 mg, 30%). 1H NMR (400 MHz, CDCI3) delta 8.5 (d, 1 H), 7.7 (m, 1H)1 7.3 (d, 1 H), 1.25 (m, 2H), 1.15 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,97483-77-7, 5-Bromopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2007/84451; (2007); 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 58483-95-7, name is 5-Amino-2-chloropyridine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

General procedure: A mixture of compound 5-amino-2-chloropyridine-4-carboxylic acid(1000 g, 5.8 mol) was dissolved in 5000 mlEthylene glycol monomethyl ether, AddedFormamidine hydrochloride(1867 g, 23.2 mol), sodium acetate (2360 g, 17.4 mol). The reaction was heated to 120 ° C for 6 hours. After the reaction was complete, the reaction was cooled to room temperature, poured into 4000 ml of water and extracted twice with ethyl acetate. The organic phase was combined, dried and concentrated to afford the crude product which was filtered to give 6-chloropyridine And [3,4-d] pyrimidin-4 (3H) ketone (924 g, 5-1 mol)

With the rapid development of chemical substances, we look forward to future research findings about 58483-95-7.

Reference:
Patent; Bide Pharmatech Ltd.; Li, Jinfei; Li, Xinling; Huang, Liangfu; Ou, Yanghao; (7 pag.)CN104130256; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58596-88-6 ,Some common heterocyclic compound, 58596-88-6, molecular formula is C6H4Cl2N2O2, 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.

(2e) 6-Chloro-5-methyl-3-nitro-2-pyridinamine [Formula 22]; A mixture of 2,6-dichloro-3-methyl-5- nitropyridine (10.41 g, 50.3 mmol), 28% aqueous ammonia solution (17 ml, 0.25 mol), potassium carbonate (10.4 g, 75.5 mmol) and t-butanol (167 ml) was stirred overnight at 60C under nitrogen atmosphere. After stirring at room temperature for 3 hours, a precipitate was filtered and then washed three times with water, thereby yielding the title compound (4.25 g, 22.7 mmol, 45%) as a yellow solid. ¹H NMR(400MHz, QMSO-D6) No. ppm; 2.23,(3H, s), 8.04(2H, br s), 8.39(1H, s).

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. 58596-88-6, 2,6-Dichloro-3-methyl-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 20173-24-4, 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.20173-24-4, name is 2-(Pyridin-3-yl)ethanamine, molecular formula is C7H10N2, molecular weight is 122.1677, as common compound, the synthetic route is as follows.

To a solution of 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde (50 mg, 0.19 mmole), 5 mL DCM and NA2S04 (134 mg, 0.95 mmole) was added 2-(pyridin-3- yl)ethan-l -amine (31 mg, 0.25 mmole) and the reaction was stirred overnight. NaBH4 (9.5 mg, 0.25 mmole) added, stir 10 minutes, 2 drops MeOH added, stir lh, quenched with water, organics separated off and evaporated. The residue was passed through a Gilson reverse phase HPLC to give {2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9- yl]ethyl}[2-(pyridin-3-yl)ethyl]amine, 65.3 mg (71%). LCMS m/z 367.1 (M + 1) observed

The chemical industry reduces the impact on the environment during synthesis 20173-24-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TREVENA, INC.; VIOLIN, Jonathan D.; SOERGEL, David G.; (177 pag.)WO2017/106547; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem