Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 6320-39-4, 3-Amino-4-hydroxypyridine, 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, Quality Control of 3-Amino-4-hydroxypyridine, blongs to pyridine-derivatives compound. Quality Control of 3-Amino-4-hydroxypyridine

To a large screw cap vial was added 3-aminopyridin-4-ol (0.440 g, 4.0 mmol) in DMF (lOmL) along with triethylamine (1.561 mL, 1 1.2 mmol), -(tert- butoxycarbonylamino)cyclopropanecarboxylic acid (0.845 g, 4.2 mmol) and finally TBTU, o-Benzotriazol-l-yl-N,N,N’,N’-tetramethyluronium tetrafluoroborate (1.605 g, 5.0 mmol). The vial was sealed and the brown mixture was shaken for 24 hours at room temperature. The reaction mixture was concentrated to an oil, taken up in acetonitrile and purified using a Shimadzu preparative HPLC employingacetonitrile/water/ammonium acetate where solvent A was 5% acetonitrile / 95% water / 10 mM ammonium acetate and solvent B was 5% water / 95% acetonitrile / 10 mM ammonium acetate with a Phenomenex-Luna IotaOmicronmuiotaeta C18 30x100mm column at a gradient of 0-100% B and a flow rate of 30mL/min. over 10 minutes with a 5 minute hold. Solvent was removed giving l.Ogram (81% yield) of tert-butyl l-(4- hydroxypyridin-3-ylcarbamoyl) cyclopropyl carbamate as a light yellow solid. The LC/MS data was obtained on a Shimadzu analytical LC /Micromass Platform LC (ESI+) at 220nm using the following set of conditions: Phenomenex Luna 3muetaiota CI 8, 2 x 50mm column, with a gradient of 0-100%B (B = 90% HPLC grade acetonitrile/ 0.1% trifluoroacetic acid/ 10% HPLC grade water), (A = 90% HPLC grade water / 0.1% trifluoroacetic acid/ 10% HPLC grade acetonitrile), in 4 minutes with a 1 minute hold at a rate of 0.8 mL/minute. HPLC purity was determined using a Shimadzu analytical LC at 254nm and 256nm with a Waters Sunfire CI 8 3.5muiotaeta 4.6 x 150mm column employing water/acetonitrile/ 0.1% trifluoroacetic acid with a gradient of 10-100% B (B = 95% HPLC grade acetonitrile/ 0.1% trifluoroacetic acid/ 5% HPLC grade water), (A = 95% HPLC grade water / 0.1% trifluoroacetic acid/ 5% HPLC grade acetonitrile), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. The HPLC purity was then confirmed with an orthogonal solvent system and column using a Shimadzu analytical LC with a Phenomenex Gemini CI 8 3.0muiotaeta 4.6 x 150mm column employing water/methanol/ lOmM ammonium bicarbonate with a gradient of 10-100%) B (B = 95% HPLC grade methanol/ lOmM ammonium bicarbonate / 5% HPLC grade water), (A = 95% HPLC grade water / lOmM ammonium bicarbonate / 5% HPLC grade methanol), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. XH NMR (400 MHz, CD3OD) delta ppm 1.17 (m, 2 H), 1.51 (s, 9 H), 1.59 (m, 2 H), 6.55 (d, J=7.03 Hz, 1 H), 7.74 (dd, J=7.03, 1.51 Hz, 1 H), 7.79 (br. s., 1 H), 8.89 (d, 1 H). LCMS rt =1.682, min., m/z 294.3(M + H). HPLC rt = 5.621min. (Sunfire C18), 94.9% purity and 7.961min. (Gemini C18), 100 % purity

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6320-39-4, 3-Amino-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; GRANT-YOUNG, Katharine, A.; KADOW, John, F.; WO2011/112769; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153034-86-7, 2-Chloro-4-iodopyridine, 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, Formula: C5H3ClIN, blongs to pyridine-derivatives compound. Formula: C5H3ClIN

l-Bromo-3-ethynylbenzene (3.76 g, 20.77 mmol), palladium(II) dicMorobis(triphenylphosphine) (73 mg, 0.10 mmol) and copper(I) iodide (0.020 g, 0.10 mmol) were dissolved in anhydrous tetrahydrofuran (15 mL) and triethylamine (10 mL). 2- Chloro-4-iodorhoyridine (4.97 g, 20.77 mmol) dissolved in anhydrous tetrahydrofuran (5 mL) was added. The reaction was stirred at room temperature over night under an atmosphere of nitrogen. The reaction was quenched with hydrochloric acid (2M aq.) and extracted with dichloromethane twice. The aquous phase was then made basic using NaOH (15% aq.) and extracted with dichloromethane twice. The combined organic phases were concentrated in vacuo and the product was purified by column chromatography using a gradient eluent (0 to 30% ethyl acetate in heptane) to give 5.38 g (89% yield) of the title compound: MS (ESI) m/z 294 [M+l]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2008/76046; (2008); 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. 138006-41-4, name is 3-Bromo-2,5-dichloropyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H2BrCl2N

Step Ml. A mixture of tert-butyl piperazine- l-carboxylate (186 mg, 0.996 mmol), 3-bromo- 2,5-dichloropyridine (226mg, 0.996 mmol), and DIEA (174 muEpsilon, 0.996 mmol) in NMP was heated at 160-165 C for 15 min. Silica gel column purification with 5% EtOAc in DCM gave tert-butyl 4-(3-bromo-5-chloropyridin-2-yl)piperazine-l-carboxylate (204mg, 0.542 mmol, 54.4 % yield). White solid. ^- MRCCDCls, 500MHz) delta 8.18 (1H, s), 7.80 (1H, s), 3.58 (4H,m), 3.26(4H,m), 1.49 (9H, s),

The synthetic route of 138006-41-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CIANCI, Christopher W.; GERRITZ, Samuel; KIM, Sean; LANGLEY, David R.; LI, Guo; PEARCE, Bradley C.; PENDRI, Annapurna; SHI, Shuhao; ZHAI, Weixu; ZHU, Shirong; WO2012/44531; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 31872-63-6, 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 31872-63-6, name is 3-Bromo-4-chloro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-bromo-4-methyl-5-nitropyridine (94a) Diethyl malonate (3.84 mL, 25.3 mmol) was slowly added to a suspension of sodium hydride (1.01 g of a 60% suspension in oil, 25.3 mmol) in DMF (15 mL) at 0 C. and stirred 30 min until gas evolution ceased. 3-bromo-4-chloro-5-nitropyridine (3.00 g, 12.6 mmol) was added slowly, and the dark reddish-brown solution was stirred at room temperature for 1 hour. The reaction was carefully quenched with water and acidified to pH 1 with 1N HCl. The aqueous mixture was extracted with EtOAc (2*150 mL). The combined organics were washed with water (100 mL) and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was diluted with 4N HCl (50 mL) and the solution refluxed 16 hours. The mixture was cooled in an ice bath and basified to pH 7 with 50% NaOH. The aqueous mixture was extracted with EtOAc (3*100 mL) and the combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford 94a (1.90 g, 70%) as a yellow solid. 1H NMR (300 MHz, CDCl3) delta 8.94 (s,1H), 8.97 (s,1H), 2.65 (s, 3H).

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 31872-63-6, 3-Bromo-4-chloro-5-nitropyridine.

Reference:
Patent; PFIZER INC; US2005/90529; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17228-64-7 ,Some common heterocyclic compound, 17228-64-7, molecular formula is C6H6ClNO, 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.

General procedure: Under Nitrogen, to a 10 mL Schlenk flask equipped with a magnetic bar, potassium hydroxide (4.5 mmol, 252 mg), phenyl boronic acid (3.15 mmol), and aryl chlorides (3 mmol) (if liquid, was injected through the septum later), catalyst 3 (0.05 mol% catalyst loading, 1 mg) were added in turn, followed by addition of 2-propanol (5 mL) and H2O (0.5 mL). The mixture was then stirred at 80 for 2 h. It was also monitored by gas chromatography. Water was added to the reaction mixture, which was extracted by ethyl acetate, dried over anhydrous Na2SO4, and the solvent was evaporated in vacuum. When necessary the product was purified by flash chromatography.

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. 17228-64-7, 2-Chloro-6-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shen, An; Hu, Yu-Cai; Liu, Ting-Ting; Ni, Chen; Luo, Yong; Cao, Yu-Cai; Tetrahedron Letters; vol. 57; 19; (2016); p. 2055 – 2058;,
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. 873107-98-3, name is 5-Iodo-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-Iodo-2-(trifluoromethyl)pyridine

In a microwave vial, 3-ethylsulfanyl-2-(1 H-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridine (274 mg, 1 .0 mmol) and 5-iodo-2-(trifluoromethyl)pyridine (409 mg, 1 .50 mmol) were dissolved in dry DMF (3 ml) and potassium carbonate (276 mg, 2.00 mmol) was added. The vial was closed and the mixture was heated in the microwave at 140C for 6 h. The reaction mixture was partitioned between EtOAc and brine/water (1/1 ). After washing and separation, the organic layer was washed with water/brine (1/1 ), dried over sodium sulfate and concentrated. The crude product was purified over silica by flash column chromatography (5 to 75% gradient of EtOAc in heptane). The fractions containing product were combined and concentrated. The crude product was again purified over silica by flash column chromatography (0 to 2.5% gradient of MeOH in CH2CI2) to afford the compound P1 .1 (221 mg) as a solid, mp 174.5-175.5C. LCMS (method 2): 420 (M+H)+, retention time 3.85 min. H-NMR (CDCI3, ppm) 1 .45 (3H), 3.07 (2H), 7.91 (1 H), 7.93 (1 H), 8.38 (1 H), 8.79 (1 H), 8.87 (1 H), 9.26 (1 H).

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, 873107-98-3, 5-Iodo-2-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; TITULAER, Ruud; EMERY, Daniel; EDMUNDS, Andrew; STOLLER, Andre; JUNG, Pierre Joseph Marcel; JEANGUENAT, Andre; BUCHHOLZ, Anke; (82 pag.)WO2016/12395; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128071-98-7, Adding some certain compound to certain chemical reactions, such as: 128071-98-7, name is 4-Bromo-2-fluoropyridine,molecular formula is C5H3BrFN, 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 128071-98-7.

Step 1: Preparation ofl-(4-bromopyridin-2-yl)cyclopropanecarbonitrile.LiHIVIDS (1 M in toluene, 17.6 mL, 17.6 mmol, 3.1 eq) was added dropwise to a cold (-5C) mixture of 4-bromo- 2-fluoropyridine (1 g, 5.7 mmol), cyclopanecarbonitrile (1.25 mL, 17 mmol, 3 eq) and4A MS in toluene (20 mL). The reaction mixture was allowed to warm to room temperature and stirred for 16 hr. After it was poured into water, the mixture was filtered. The filtrate was diluted with EtOAc and 1120, and extracted with EtOAc. The organic phase was washed with water and brine, dried over anhydrous Na2504, and concentrated. The residue was purified by column chromatography using PE/EtOAc (9:1) as eluent to give the desired product. LC-MS: m/z 223.0 (M+H).

According to the analysis of related databases, 128071-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; ZAHLER, Robert; CAI, Zhenwei; ZHOU, Ding; WO2015/3640; (2015); 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 4214-73-7, name is 2-Amino-5-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Amino-5-cyanopyridine

To a solution of compound 53.9 (10 g, 83.95 mmol, 1 eq) in THF (150 mL) wasadded LAH (6.37 g, 167.90 mmol, 2 eq) at 0C. The mixture was stirred at 0C for 1.5 hours.The reaction mixture was quenched by addition saturated sodium sulfate at 0 C and added100 ml H20 then extracted with ethyl acetate (100 mL x 3). The combined organic layerswere washed with saturated brines (30 mL x 1), dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressure to give the product compound 53.8 (7.50 g, 61.42mmol, 73.16% yield) as a yellow oil. LCMS (ESI): m/z: [M + H] called for C6H6N20: 123;found 123; RT=0.099 mm.

With the rapid development of chemical substances, we look forward to future research findings about 4214-73-7.

Reference:
Patent; CORTEXYME, INC.; LYNCH, Casey C.; KONRADI, Andrei; GALEMMO, JR., Robert A.; (218 pag.)WO2018/209132; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]pyridine, 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, Product Details of 74420-15-8, blongs to pyridine-derivatives compound. Product Details of 74420-15-8

[0383] Example lb: 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (7a) [0384] 3-bromo-lH-pyrrolo[2,3-b]pyridine (6a) (10.7 kg, 54.3 moles) was added to 94.3 kg of THF in a 200 L glass-lined reactor. The solid was dissolved completely by stirring. After the mixture was cooled to about 10-15 C, NaH (3.4 kg, 85 moles) was added in portions (about 200-250 g each portion) every 3 to 5 minutes while venting any H2 gas released by the reaction. After the addition of NaH, the mixture was stirred for one hour while maintaining the temperature of about 10-20 C. 4-methylbenzenesulfonylchloride (12.4 kg, 65.0 moles) was added at a rate of 0.5 kg/10 minutes at about 10-20 C. After the addition was complete, the temperature was maintained at about 10-20 C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-lH-pyrrolo[2,3- bjpyridine (6a) was less than 1% (after about 1.5 hours). [0385] The reaction was quenched with water (10.7 kg) while maintaining the temperature below 20 C. Dichloromethane (41.3 kg) was added to the mixture. Then 3% HC1 (42.8 kg) was added into the mixture while maintaining the temperature below 25 C. After the addition, the phases were allowed to separate for 0.5 hour. The aqueous phase was extracted twice with dichloromethane. During each extraction, the mixture was stirred for 15 minutes and then held for 15 minutes. All the organic phases were combined. The combined organic phases were washed with 3% HC1 (33.4 kg) and water (40 kg). During each wash, the mixture was stirred for 15 minutes and then held for 30 minutes. [0386] The mixture was transferred into a 50 L vacuum filter and filtered through silica gel (3 kg). The cake was washed with dichloromethane (35 kg) twice. The filtrate and washings were combined. The organic phase was concentrated below 40 C under vacuum of a pressure less than -0.085 MPa until 10 L mixture remained. Petroleum ether (9kg) was added into the residue. The mixture was stirred until it was homogeneous. The slurry was transferred into a 50 L vacuum filter and filtered. The cake was washed with petroleum ether (9 kg). A light brown solid resulted (17 kg, 99.7% purity as measured by HPLC analysis (method A), 94% yield of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (7a)).

The synthetic route of 74420-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; TANOURY, Gerald, J.; JUNG, Young, Chun; MAGDZIAK, Derek; LOOKER, Adam; WO2013/6634; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14254-57-0, 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.14254-57-0, name is Isonicotinoyl chloride, molecular formula is C6H4ClNO, molecular weight is 141.5551, as common compound, the synthetic route is as follows.

To a suspension of indigo (1.0 g, 3.8 mmol) in anhydrous ethyl acetate (50m1) containing sodium acetate (0.8 g, 9.5mmol) and zinc (2.49 g, 38 mmol) was added isonicotinoyl chloride (2.0 g, 11.4 mmol). The reaction mixture was allowed to stir for 30 mins at 40C. The suspension was allowed to cool to room temperature and then concentrated to dryness. The residue was extracted with hot acetone. The crude material was purified using flash column chromatography eluting with 20% ethyl acetate: pet ether. The product was isolated as a pale yellow solid and was confirmed by ?H NMR to be the di-substituted product, Compound 22(0.4g, 22%). Mw, C28H18N404, 474.47; ?H NMR (400 MHz, DMSO) oe 11.36 (s, 1H), 11.12 (s, 1H),7.59 (d, J 8.0 Hz, 1H), 7.50 (dd, J 8.1, 0.9 Hz, 1H), 7.46 – 7.41 (d, 8.1 Hz, 1H), 7.36 (d, J=8.1 Hz, 1H), 7.16 (dddd, J= 12.9, 8.2, 7.0, 1.2 Hz, 2H), 7.05 (ddt, J 8.1, 7.0, 1.1 Hz, 2H), 6.84(dd,J= 2.1, 0.8 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 14254-57-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VF JEANSWEAR LP; PUVVADA, Sudhakar; SCHEER, Dennis; HOERTZ, Paul, Gerard; (146 pag.)WO2019/126469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem