Pyridine-derivatives

Synthetic Route of 1150617-54-1, 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 1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

[00302] To a solution of 6-bromo-1H-pyrazolo[4,3-b]pyridine (145 mg, 0.732 mmol) in THE (4.1 niL) at ii was added NaH (60:40 sodium hydride:mineral oil, 37.0 mg, 0.925 mmol). The mixture was allowed to stir for 5 mm and then cooled in ice bath. Cyclopropanesulfonylchloride (95.0 uL, 0.9 19 mmol) was added dropwise and the mixture was allowed to stir for 2 h while the bath temperature warmed to between 10-15 C. The reaction mixture was quenched with ammonium chloride (2M aq. solution, 5 mL) and was partitioned between EtOAc and water. The aqueous layer was further extracted with EtOAc and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated by rotary evaporation. An LCMS of the crude material showed ?-4:1 mixture of isomers. The residue was purified by column chromatography to provide a mixture of 6-bromo-1-(cyclopropylsulfonyl)-1H-pyrazolo[4,3-b]pyridine LCMS (AA): m/z 304.3 (M+H), second peak, and 6- bromo-2-(cyclopropylsulfonyl)-2H-pyrazolo[4,3-b]pyridine LCMS (AA): m/z 304.3 (M+H), first peak (combined yield 201 mg, 90.8%).

According to the analysis of related databases, 1150617-54-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; WONG, Tzu-Tshin; XU, He; XU, Tianlin; YE, Yingchun; WO2015/108861; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13362-78-2 , The common heterocyclic compound, 13362-78-2, name is (E)-1,2-Di(pyridin-4-yl)ethene, molecular formula is C12H10N2, 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: To a stirred solution of HL (95.6mg, 0.4mmol) in absolute EtOH (10ml), solid Zn(OAc)2·2H2O (43.9mg, 0.2mmol) and absolute bpe (trans-1,2-bis(4-pyridyl)ethylene, 18mg, 0.1mmol) were added separately, and the final mixture was heated under reflux for 5h. A solution of Ln(NO3)3·6H2O (0.2mmol, Ln=Nd, 0.087g; Ln=Yb, 0.089g; Ln=Er, 0.088g; Ln=Gd, 0.090g) in absolute MeCN (20ml) were added sequentially. Then the mixture was refluxed for another 3h. The respective yellow clear solution was then cooled to room temperature and filtered. Diethyl ether was allowed to diffuse slowly into the respective solution at room temperature and pale yellow microcrystallines 5?8 were obtained in about three weeks, respectively.

The synthetic route of 13362-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Zhao; Feng, Weixu; Su, Peiyang; Liu, Han; Zhang, Yao; Wang, Zheng; Miao, Tiezheng; Lue, Xingqiang; Fan, Daidi; Wong, Wai-Kwok; Jones, Richard A.; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 116; (2013); p. 102 – 110;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 66521-66-2, 4-(Pyridin-3-yl)pyrimidin-2-amine, 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, 66521-66-2, blongs to pyridine-derivatives compound. Product Details of 66521-66-2

Into a three-neck round bottom flask was added raw material compound 5 (0.21 g, 1.2 mmol), and addedsolvent anhydrous 1,4-dioxane 25 mL, catalyst CuI (0.095 g, 0.5 mmol), cocatalyst KI (0.25 g, 1.5). Mmmol),acid binding agent K 2 CO 3 (1.4 g, 2.0 mmol). Then in N 2 The reaction 3-ethyl 4-bromo-4-methylbenzoate(0.243 g, 1.5 mmol) and the ligand DMEDA (60 muL, 0.5 mmol) were added under stirring, and the mixturewas stirred and warmed to 100 C for 20 h. After the reaction was completed, the mixture was cooled to 45 C, and 2 ml of concentrated aqueous ammonia was added to the reaction mixture, and the mixture was stirredfor 30 min, then the system was cooled to room temperature, and the residue was filtered, extracted with ethylacetate 3-4 times, and the organic phases were combined and dried. The mixture was evaporated to dryness,and purified by column chromatography to afford compound 6 (0.15 g, yield: 45%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66521-66-2, its application will become more common.

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

Reference of 52833-94-0, 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 52833-94-0 as follows.

Step 2: 5-Bromo-3-(3-(difluoromethyl)-1 ,2,4-oxadiazol-5-yl)pyridin-2-amine To a stirring suspension of 2-amino-5-bromonicotinic acid (500 mg, 2.304 mmol) in DCM (11.5 ml) was added 1-chloro-N,N,2-trimethyl-1-propenylamine (Ghosez’s reagent) (0.366 ml, 2.76 mmol). The reaction mixture was left stirring for 1.5 hrs. 2,2-Difluoro-N’- hydroxyacetimidamide (step 1) (507 mg, 4.61 mmol) was added followed by DIPEA (0.805 ml, 4.61 mmol) and the mixture was stirred overnight. T3P (4.04 ml, 6.91 mmol) was added and the mixture was heated using microwave radiation for 135 mins at 100C. The mixture was added to water (100ml) and the product extracted into EtOAc (2 x 90ml). The organic phase was washed with brine, dried over MgS04 and concentrated to dryness. The crude product was purified by flash column chromatography, eluting with 0-10% gradient of (2M NH3 in MeOH) in DCM on a 24g Si-column to afford the title compound; LCMS: Rt = 1.11 mins; MS m/z 291.4 [M+H]+; Method 2minl_owpHv01 1H NMR (400 MHz, DMSO-d6) delta 8.43 (1 H, d), 8.39 (1 H, d), 7.55 (2H, br s), 7.47 (1 H, t).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52833-94-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; WO2015/162456; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17368-12-6 , The common heterocyclic compound, 17368-12-6, name is 2-Chloro-4-hydroxypyridine, molecular formula is C5H4ClNO, 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.

A mixture of 3-bromo-2-ethyl-6-nitropyridine (3.168 g, 13.71 mmol), 2-chloro-4-hydroxypyridine (3.55 g, 27.4 mmol) and K2CO3 (5.69 g, 41.1 mmol) in DMA (25 mL) was sparged with Ar and heated at 105 C. overnight. The mixture was cooled to RT, treated with EtOAc, washed successively with 10% K2CO3, 5% LiCl, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (1.102 g, 28%). MS (ESI) m/z: 280.0 (M+H+).

The synthetic route of 17368-12-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67346-74-1, 3-Ethynylpyridin-2-amine, 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, Safety of 3-Ethynylpyridin-2-amine, blongs to pyridine-derivatives compound. Safety of 3-Ethynylpyridin-2-amine

To a mixture of (6-(4-fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chloride (25 mg) described in Manufacturing Example 75-1-4 and tetrahydrofuran (1 mL) were added 3-ethynyl-pyridin-2-ylamine (6.0 mg, 0.051 mmol) described in Manufacturing Example 1-2-3 and triethylamine (21 muL, 0.15 mmol), which was stirred for 5 hours at 55 C. The reaction mixture was cooled to room temperature and water was added thereto at that temperature, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=2:1) to obtain the title compound (5.9 mg, 32%). 1H-NMR Spectrum (CDCl3) delta (ppm): 4.02 (2H, s), 5.41 (2H, br s), 6.27 (1H, s), 6.73 (1H, dd, J=4.8, 7.7 Hz), 6.90 (1H, d, J=8.4 Hz), 7.06-7.12 (4H, m), 7.62 (1H, dd, J=2.6, 8.4 Hz), 7.71 (1H, dd, J=1.7, 7.6 Hz), 8.13 (1H, d, J=2.6 Hz), 8.16 (1H, dd, J=1.7, 4.9 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67346-74-1, 3-Ethynylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, 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 69950-65-8, blongs to pyridine-derivatives compound. Product Details of 69950-65-8

Methyl 6-[hydroxy[6-methoxy-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridin-3-yl]methyl]pyridi ne-2-carboxylate n-Butyllithium (0.5 mL, a 2.6 mol/L n-hexane solution) was added to a tetrahydrofuran solution (2.8 mL) of 3-bromo-6-methoxy-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridine (410 mg) at -78C under an argon atmosphere, and then the mixture was stirred at -78C for 30 minutes. A tetrahydrofuran solution (2.8 mL) of methyl 6-formylpyridine-2-carboxylate (360 mg) was added to the obtained mixture at -78C, and then the mixture was stirred at room temperature for 1 hour. A saturated ammonium chloride aqueous solution was added to the reaction mixture and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was evaporated and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 4:1) to obtain a title compound as yellow liquid (303 mg). 1H-NMR (400 MHz, CDCl3) delta 0.53 (9H, s), 3.77 (3H, s), 4.07 (3H, s), 5.35 (1H, d, J = 2.4 Hz), 6.31 (1H, d, J = 2.4 Hz), 6.87 (1H, d, J = 9.7 Hz), 7.04 (1H, d, J = 9.7 Hz), 7.28 (1H, d, J = 7.9 Hz), 7.40 (1H, tt, J = 7.9, 1.8 Hz), 7.47 (2H, t, J = 7.9 Hz), 7.72 (1H, t, J = 7.9 Hz), 7.87-7.91 (2H, m), 8.04 (1H, d, J = 7.9 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Kissei Pharmaceutical Co., Ltd.; SETO, Shigeki; UMEI, Kentaro; NISHIGAYA, Yosuke; TANIOKA, Asao; KONDO, Tatsuhiro; KONDO, Atsushi; TATANI, Kazuya; KAWAMURA, Naohiro; EP2669285; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 133627-47-1, name is N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide. A new synthetic method of this compound is introduced below., Recommanded Product: 133627-47-1

EXAMPLE 5 Preparation of 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (Nevirapine) Using sodium Hexamethyldisilazane A reaction flask equipped with a magnetic stirrer, temperature controller thermodouple, addition funnel and condenser with an oil bubbler for exclusion of ambient air was inerted with nitrogen and charged with 3.02 g (0.010 mol) of N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide from Example 4 and 30 ml of anhydrous THF. A 40% solution of sodium hexamethyldisilazane in THF (12.7 ml, 0.025 mol) was added dropwise maintaining the temperature of the reaction mixture at no more than 30 C. When the addition of the NaHMDS solution was completed, the reaction mixture was heated to reflux temperature (about 63-66 C.).When the reaction was completed (HPLC analysis), the mixture was cooled to ambient temperature.The reaction mixture was treated with 1.55 g (0.050 mol) of methanol and 0.45 g of water (0.025 mol).The mixture was concentrated on a rotary evaporator at 25-30 in.Hg with a 50-60 water bath temperature.The residual product weighing 4.44 g was triturated with 50 ml of water and the PH 10-12 solution was acidified to PH 3 by adding 10% HCl solution.The solid product was collected by filtration and the filter cake rinsed three times with 10 ml portions of water.The filter cake was dried in a vacuum oven at 50-60 C. to obtain nevirapine.

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, 133627-47-1, N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide.

Reference:
Patent; Boehringer ingelheim Chemicals, Inc.; US2004/2603; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 67058-76-8, Adding some certain compound to certain chemical reactions, such as: 67058-76-8, name is 3-Bromo-1H-pyrrolo[2,3-c]pyridine,molecular formula is C7H5BrN2, 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 67058-76-8.

Sodium hydride (60 % in mineral oil) (217 mg) was added to a stirred solution of 3-bromo- 1 /-/-pyrrolo[2,3-c]pyridine (535 mg) in DMF (5 ml) that had been cooled in an ice bath to 0 C and placed under nitrogen. The mixture was stirred for 30 min, until hydrogen evolution ceased, and then 4-nitrobenzenesulfonyl chloride (662 mg) was added. The mixture was stirred at 0 C for 1 hour. The mixture was then warmed to RT and stirred for a further 30 min. The solution was poured into stirring water (10 ml) and rapidly stirred for 15 min. The resulting brown solid was collected by filtration, washed with water and dried in a vacuum oven at 50 C to give a yellow solid. This crude material was purified by FlashMaster II. The residue was dissolved in DCM:methanol (1 :1 ) and pre adsorbed onto silica. This was added to the top of a 20 g silica SPE cartridge that was subsequently eluted with 0 – 50 % ethyl acetate:cyclohyexane over 40 min. The product-containing fractions were combined and the solvent removed in vacuo to give the title compound, 233 mg as a white solid. LCMS (Method B): Rt = 1.01 min, MH+ = 384.

According to the analysis of related databases, 67058-76-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian, Robert; DOWN, Kenneth, David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie, Nicole; LE, Joelle; LUNNISS, Christopher, James; PARR, Nigel, James; RITCHIE, Timothy, John; ROBINSON, John, Edward; SIMPSON, Juliet, Kay; SMETHURST, Christian, Alan, Paul; WO2011/67364; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-2-chloropyridine, 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, 14432-12-3, blongs to pyridine-derivatives compound. name: 4-Amino-2-chloropyridine

Preparation 7: 2-Chloro-5-iodo-pyridin-4-ylamine N-lodosuccinimide (24.75 g, 110.0 mmol) was added to a solution of 2-chloro-pyridin-4-ylamine (12.85 g, 100.0 mmol) in acetonitrile (400 mL) and the mixture stirred and held at reflux overnight. Upon cooling to room temperature the solvent was removed in vacuo and residue partitioned between EtOAc (250 mL), saturated sodium thiosulfate (100 mL) andwater (250 mL). The organic layer was separated, washed with water (2 >< 250 mL), separated and the solvent removed in vacuo to afford an orange oil that was subjected to column chromatography on silica. Gradient elution with 30-50% EtOAc in petrol afforded a pale orange solid that was rinsed with 25% EtOAc in petrol (80 mL). Solids were collected by filtration and sucked dry to afford the title compound (7.32 g) as an off-white solid. Themother liquors were concentrated to dryness in vacuo and the residues subjected to columnchromatography on silica. Elution with 30-50% EtOAc in petrol afforded further pure material(1.90 g). Combined yield : (9.22 g, 36%) 1H NMR (DMSO-d6) 8.20 (1H, 5), 6.64 (1H, 5), 6.50(2H, br 5). MS: [M+H] 255. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common. Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; BUCK, Ildiko Maria; DAY, James Edward Harvey; HOWARD, Steven; SAXTY, Gordon; MURRAY, Christopher William; WO2014/60770; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem