Pyridine-derivatives

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. 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C12H9ClN2O3

The above product (13.2 g, 0.05 mol), iron powder (11.2 g, 0.2 mol) and 12 M HCl (4 mL, 0.05 mol) were added into 90% EtOH/H2O (200 mL) and the reaction mixture was stirred at 70 C for 1 h. The dark solution was filtered through a Celite pad. The filtrate was concentrated and the residual was dissolved in CH2Cl2 (200 mL). The organic layer was washed twice with water, and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to give 26 (10.9 g, 93%) as a light-yellow solid. Mp 90.9-91.8 C; MS-EI (m/z): 93, 142, 199, 234(M+); 1H NMR (DMSO-d6, delta): 4.95(s, 2H), 5.07(s, 2H), 6.45(dd, 1H), 6.65(d, 1H), 6.90(d, 1H), 7.35(t, 1H), 7.55(d, 1H), 7.85(t, 1H), 8.55(d, 1H).

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, 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine.

Reference:
Article; Mao, Yongjun; Zhu, Wenxiu; Kong, Xiaoguang; Wang, Zhen; Xie, Hua; Ding, Jian; Terrett, Nicholas Kenneth; Shen, Jingkang; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3090 – 3104;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 144657-66-9 , The common heterocyclic compound, 144657-66-9, name is tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, molecular formula is C13H14N2O3, 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 isopropylamine (0.52 mL , 6.09 mmol) was added l-(tert- butoxycarbonyl)-3-formyl-7-azaindole (1.50 g, 6.09 mmol) in 10 mL MeOH. The solution was stirred at ambient temperature for 2h. Sodium borohydride (576 mg, 15.2 mmol) was added, and the reaction mixture was stirred for 16h at ambient temperature. The mixture was concentrated and partitioned between 10% K2CO3 and ether. The organics were washed with water and brine, then dried over Na2S04, filtered and concentrated. The crude product was carried on to the next step. LCMS [M+H]+ = 190.2.

The synthetic route of 144657-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn, J.; EGBERTSON, Melissa; BRNARDIC, Edward; JONES, Kristen; SANDERS, John, M.; HENZE, Darrell, A.; WO2013/176970; (2013); A1;,
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. 53344-73-3, name is 2-Chloro-4,4′-bipyridine, the common compound, a new synthetic route is introduced below. Formula: C10H7ClN2

A mixture of 1.3 g of 2-chloro-4,4′-bipyridine and 6.5 ml of anhydrous hydrazine in 40 ml of dry pyridine was refluxed for 24 hours under argon and then concentrated. The residue was dissolved in methylene chloride, treated with activated carbon and the solvent was removed giving an oil which was crystallized from ether-hexane-methylene chloride. A 1.3 g portion of these crystals of 2-hydrazino-4,4′-bipyridine was combined with 50 ml of triethyl orthoacetate and heated on a steam bath for 1 hour. After standing overnight, hexane was added and after further standing, crystals separated. These crystals were collected and recrystallized from acetonehexane, giving the desired product as off-white crystals, mp 223-226 C.

The synthetic route of 53344-73-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4550166; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, 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 solution of Br2 (0.25 mL, 4.87 mmol) in HO Ac (3 mL) was added dropwise to a stirring solution of 6-(trifluoromethoxy)pyridin-3-amine (400 mg, 2.25 mmol) in EtOH (15 mL) and HO Ac (1.5 mL) at 0C under a nitrogen atmosphere. After addition was complete, the reaction was warmed to room temperature and was allowed to stir for an additional 15 hours. The reaction mixture was concentrated. DCM (30 mL) and saturated aqueous NaHC03 (20 mL) were added to the crude residue. The aqueous layer was extracted with DCM (50 mL x 3). The combined organic layers were dried over Na2S04, filtered and concentrated. The crude residue was purified by column chromatography (0-10% EtOAc in petroleum ether) to give 2,4- dibromo-6-(trifluoromethoxy)pyridin-3-amine (670 mg, yield: 89%) as light yellow solid. 1H NMR (400 MHz, CDCl3): d = 7.18 (s, 1H), 4.59 (s, 2H).

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 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79491-46-6, 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. 79491-46-6, name is 2,6-Dibromo-3-methoxy-5-nitropyridine, molecular formula is C6H4Br2N2O3, 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.

5.43 3-Methoxy-5-nitropyridine-2,6-diamine (33) A solution of 32 (0.5 g, 1.6 mmol) in aqueous ammonia (15 M, 12 mL, 180 mmol) was heated at 90 C for 1 h in a microwave oven. The reaction mixture was cooled, the yellow solid was collected by filtration, washed with a small amount of water, and dried under vacuum to afford 33 (230 mg, 78%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6, 393 K) delta = 7.48 (s, 1H), 7.35 (br, 2H), 6.81 (br, 2H), 3.80 (s, 3H); MS ES+ve m/z 185 (M+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 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine.

Reference:
Article; Miah, Afjal H.; Abas, Hossay; Begg, Malcolm; Marsh, Benjamin J.; O’Flynn, Daniel E.; Ford, Alison J.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Steve A.; Rumley, Sally-Anne; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4298 – 4311;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

Example 29Step A6-Bromonicotinonitrile. 6-Chloronicotinonitrile (13.8 g, 100 mmol) was heated at 145 C in phosphorus tribromide (150 ml.) for 32 h. After cooling, the mixture was concentrated in vacuo. To the residue was added phosphorus tribromide (150 ml_), and the mixture was heated at 145 C for another 32 h. After cooling, the mixture was concentrated in vacuo, and an ice-water mixture (500 ml.) was added. Sodium bicarbonate was added to neutralize the mixture, and the product was extracted with ethyl acetate (3 chi 250 ml_). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was chromatographed (hexanes-ethyl acetate) to give 14.9 g (81 %) of 6-bromonicotinonitrile as a white solid: 1 H NMR (400 MHz, CDCI3) S 7.66 (d, J = 1 1.0 Hz, 1 H), 7.80 (dd, J = 3.1 , 1 1.0 Hz, 1 H), 8.67 (d, J = 3.1 Hz, 1 H); MS (M+H)+ m/z=183.0, 185.0.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; BURGESS, Gary; WO2012/114223; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256789-09-9, Adding some certain compound to certain chemical reactions, such as: 1256789-09-9, name is Methyl 6-chloro-2,4-dimethylnicotinate,molecular formula is C9H10ClNO2, 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 1256789-09-9.

a) Synthesis of 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylesterTo a solution of 710 mg, (3.6 mmol) 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester in CCI4 (16 ml) were added 688 mg (3.90 mmol) N-bromosuccinimide, 59 mg (0.36 mmol) AIBN and 210 muIota (3.72 mmol) acetic acid . The reaction mixture was irradiated with a 200W Wolfram lamp at 60 C for 24 h. The mixture was then filtered through celite, washed with CCI4 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue a mixture of 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester, 4-(bromomethyl)-6- chloro-2-methyl-pyridine-3-carboxylic acid methylester and 2-(bromomethyl)-6-chloro-4- methyl-pyridine-3-carboxylic acid methylester was obtained. This mixture was dissolved in dioxane (10 ml) and added at 0 C to a solution prepared by dissolving 594 mg (25.8 mmol) sodium in MeOH (11 ml) at 0 C. This reaction mixture was stirred at RT for 3 h. Then the reaction solution was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue again a mixture of 6-chloro-4-(methoxymethyl)-2-methyl- pyridine-3-carboxylic acid methylester and 6-chloro-2-(methoxymethyl)-4-methyl-pyridine-3- carboxylic acid methylester was obtained. This material was dissolved in NMP (7.8 ml) and 860 muIota (9.85 mmol) morpholine and 1.36 g (9.85 mmol) K2C03 were added followed by heating at 100 C for 5 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 90 mg (0.32 mmol, 9%) 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylester.

According to the analysis of related databases, 1256789-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 693286-31-6, Adding some certain compound to certain chemical reactions, such as: 693286-31-6, name is 4,6-Dichloro-2-methylnicotinic acid,molecular formula is C7H5Cl2NO2, 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 693286-31-6.

To a solution of 4, 6-dichloro-2-methyl-nicotinic acid (8. 5 g, 41.3 mmol) in anhydrous tetrahydrofuran (85 mL), 1,3-dicyclohexyl-carbodiimide (9.27 g, 44.9 mmol), 4- (DIMETHYLAMINO)-PYRIDINE (140 mg, 1.14 mmol), and cyclopentanol (5.1 mL, 4. 83 g, 56.2 mmol) are added in succession. The mixture is stirred for 15 minutes at room temperature and brought to reflux at which it is maintained for 1 hour. The reaction is cooled to ambient temperature and all volatiles are removed in vacuo. The residue is dissolved in a mixture of ethyl acetate and hexane (1: 12,200 mL) and the resultant suspension is filtered over a small pad of silica gel (45 g), which is subsequently rinsed with additional 200 mL of the same mixture of hexane and ethyl acetate. The obtained solution is concentrated in vacuo and the residue chromatographed on silica gel (hexane: ethyl acetate 15: 1) to afford 4, 6-dichloro-2- methyl-nicotinic acid cyclopentane ester as colorless oil.

According to the analysis of related databases, 693286-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/43925; (2004); A2;,
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.39774-26-0, name is 2-Bromo-6-phenylpyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Bromo-6-phenylpyridine

To a solution of 21-1 (2.70 g, mixture from previous step) in tetrahydrofuran (50 mL) cooled to -78 C. under nitrogen, n-butyllithium (2.5 M in hexanes, 5.8 mL, 14.5 mmol) was added dropwise. The mixture was stirred for 45 minutes then N,N-dimethylformamide (1.80 mL, 23 mmol) was added. The mixture was stirred at -78 C. for 1 hour, warmed to room temperature, quenched with water, and extracted with ethyl acetate. The organic layer was washed three times with water, once with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with 2.5% followed by 5% ethyl acetate in hexanes to give 6-phenylpicolinaldehyde (21-2, 1.24 g) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39774-26-0, 2-Bromo-6-phenylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, 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. Computed Properties of C6H5F3N2

The compound of Example 36A(1 g, 6.2 mmol), trifluoroacetic anhydride (1.30 g, 6.2 mmol) and pyridine(0. 54 g, 6.8 mol) are dissolved in tetrahydrofuran (20ml) under an argon atmosphere. The solution is cooled to-78 C with stirring and lithium diisopropylamide (3.0 ml of a 2 M solution in THF/heptane, 6.0 mmol) is added dropwise. The reaction mixture is allowed to warm to room temperature, and then stirred at room temperature overnight. The reaction is quenched with water and extracted with ethyl acetate (3 x 100 ml). The ethyl acetate phase is washed with brine, dried with magnesium sulphate monohydrate, filtered and concentrated to give a yellow oil. The oil is purified by flash chromatography on silica gel with cyclohexane/ethyl acetate mixtures as eluent. Yield: 1.05 g (66%of th.) HPLC (method 8): Rt = 4.23 min MS(EI) :m/z = 259(M+H)”IHh R (300 MHz, DMSO-d6) :8 = 8. 46 (s, 1H) ; 8.84 (s, 1H) ; 9.10 (s, 1H) ;11. 80 (s,1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/20412; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem