Pyridine-derivatives

Application of 138116-34-4, 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 138116-34-4 as follows.

Step 5: To a stirred solution of (4-aminopyridin-3-yl)methanol (200 mg, 1.61 mmol) in dimethylformamide were added imidazole (219 mg, 3.22 mmol, 2 eq) and tert-butyldimethylchlorosilane (267 mg, 1.77 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for 5 h. The mixture was dissolved in ethylacetate and washed with water several times. The organic layer was dried over MgSO4 and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography get 3-((tert-butyldimethylsilyloxy)methyl)pyridin-4-amine (325 mg, 85%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,138116-34-4, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/29961; (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. 174610-12-9, name is 1H-Pyrrolo[2,3-c]pyridin-5-amine, the common compound, a new synthetic route is introduced below. Product Details of 174610-12-9

General procedure: To a solution of the corresponding amine (4 or 5, 1.2 equiv), dihalo-substituted benzoic acid (2c, 2d, 2e or 2f, 1.0 equiv), and 1-hydroxybenzotriazole hydrate (HOBt, 1.2 equiv) in DMF (8.0-10.0mL/mmol; extra dry over molecular sieves, 99.8%, Acros) were added EDC-HCl (1.2 eqiv) and DIPEA (2.5 equiv). The mixture was stirred at room temperature until completed conversion (TLC control: CH2Cl2/MeOH 9/1 v/v). Then, the solvent was removed in vacuo and the residue washed with water (20mL/mmol) and dried at 70C. The crude product was purified by column chromatography on silica gel (eluent: CH2Cl2/MeOH 9/1 v/v) following by reversed phase HPLC (for purification methods, see Supporting Information, TableS2) and/or recrystallization as described below.

The synthetic route of 174610-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tzvetkov, Nikolay T.; Stammler, Hans-Georg; Hristova, Silvia; Atanasov, Atanas G.; Antonov, Liudmil; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 793 – 809;,
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Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 909720-21-4, 2,3-Dibromo-6-methoxypyridine, 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, SDS of cas: 909720-21-4, blongs to pyridine-derivatives compound. SDS of cas: 909720-21-4

1,4-Dioxane (450 mL) and water (150 mL) were added to a mixture of 2,3- dibromo-6-methoxypyridine (12 g, 45 mmol), C2 (31.8 g, 135 mmol), di(l -adamantyl)- ?- butylphosphine (cataCXium A; 3.22 g, 8.98 mmol), palladium(ll) acetate (3.03 g, 13.5 mmol), and cesium carbonate (87.9 g, 270 mmol), and the reaction vessel was evacuated and charged with nitrogen. This evacuation cycle was repeated twice, and the reaction mixture was then stirred at reflux for 20 hours. After the reaction mixture had been partitioned between ethyl acetate (300 mL) and saturated aqueous sodium chloride solution (200 mL), the aqueous layer was extracted with ethyl acetate (2 x 200 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was treated with triethylamine (3 mL), dissolved in dichloromethane and treated with silica gel; this mixture was concentrated to dryness and used for silica gel chromatography (Gradient: 0% to 6% ethyl acetate in petroleum ether) to afford the product as a brown oil. Yield: 10 g, 27 mmol, 60%. LCMS m/z 388.0 [M+Na+]. 1H NMR (400 MHz, CDCI3) delta 7.39 (d, J=8.3 Hz, 1H), 6.52 (d, J=8.3 Hz, 1H), 4.63 (dd, J=4.0, 2.8 Hz, 1H), 4.58 (dd, J=4.0, 2.8 Hz, 1H), 4.19-4.1 1 (m, 1H), 3.94-3.71 (m, 4H), 3.89 (s, 3H), 3.58-3.42 (m, 3H), 3.05 (t, J=7.2 Hz, 2H), 2.89 (t, J=7.2 Hz, 2H), 1.86-1.74 (m, 2H), 1.74-1.64 (m, 2H), 1.62-1.44 (m, 8H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,909720-21-4, 2,3-Dibromo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; HENDERSON, Jaclyn Louise; YOUNG, Joseph Michael; WAGER, Travis T.; KORMOS, Bethany Lyn; PATEL, Nandini Chaturbhai; SCIABOLA, Simone; TUTTLE, Jamison Bryce; VERHOEST, Patrick Robert; TUCKER, Joseph Walter; (181 pag.)WO2017/122116; (2017); 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. 19230-57-0, name is 2-Bromo-3-methylpyridine 1-oxide, molecular formula is C6H6BrNO, 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. COA of Formula: C6H6BrNO

To a stirred solution of 2-bromo-3-methyl pyridine-1-oxide (25g) and pyridine (42g) in acetonitrile (250mL) at about 70C, was added a solution of trifluoromethanesulfonic anhydride (55g) in acetonitrile (5OmL). The reaction mixture was stirred for about lh atabout the same temperature. The mixture was cooled to about 10C to about 15C and ethanolamine (80.52g) was added to it. The reaction mixture was stirred for about 3h at about room temperature and water and ethyl acetate were added to it. The two layers were separated and the organic layer was washed with saturated brine solution, dried and concentrated under reduced pressure at about 40C. The residue was purified by columnchromatography (15-20% ethyl acetate in hexane). Yield: 4g (16%)?H NIVIR (300IVIHz, CDC13): oe 7.26-7.24 (d,J8.lOHz,1H), 6.42-6.39 (d,J8.4Hz,1H), 4.28 (brs,2H), 2.22 (s,3H)?3CNMR(400MHz, CDC13): 156.52, 141.56, 140.50, 122.99, 107.26, 20.58 IR: 3364, 3199, 2913, 1635, 1601, 1373, 1058, 819 cm4-Amino-2-bromo-3-methyl pyridine (3g) was obtained which was eluted at 25-30% ethyl acetate in hexane.?H NIVIR (300IVIHz, CDC13): oe 7.82-7.80 (d,J5.4Hz,1H), 6.48-6.46 (d,J 5.4Hz,1H), 4.35 (brs,2H), 2.21 (s,3H)?3CNMR(400MHz, CDC13): 152.70, 146.94, 145.05, 116.88, 109.25, 15.73

With the rapid development of chemical substances, we look forward to future research findings about 19230-57-0.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; BHIRUD, Shekhar Bhaskar; KADAM, Suresh Mahadev; KANSAGRA, Bipin Parsottam; BHADANE, Shailendra Nilkanth; KALE, Shrikrishna Kantilal; PATIL, Ulhas Digambar; (57 pag.)WO2017/56031; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 769-28-8, 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, 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, 769-28-8, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

To the suspension of 3-cyano-4,6,-dimethyl-2-pyridone (3 g, 0.02 mol) and powdered NaOH (0.80 g, 0.02 mol) in dry DMF (10 ml) stirred at r.t. for 15 min was added 1,3-dibromopropane (2.02 g, 0.01 mol) slowly with constant stirring [41]. The reaction mixture was stirred at room temperature for 12 h. Completion of reaction was confirmed via TLC. There were 3 spots visualized on TLC indicating the formation of region isomers. DMF was removed under reduced pressure using rotavapour and the product was treated with 1:1 CHCl3:H2O system (300 ml). The organic layer was collected and the aqueous layer was washed three times with 300 ml of CHCl3 (100 ml each). The organic layers were combined and washed with water (100 ml) and dried over anhydrous Na2SO4. Column chromatography was done for separation of regioisomers. The first fraction collected at 20% ethyl acetate:hexane was characterized as title compound. This was crystallized with 5% ethyl acetate:hexane and ethyl acetate solution, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,769-28-8, its application will become more common.

Reference:
Article; Tewari, Ashish Kumar; Singh, Ved Prakash; Dubey, Rashmi; Puerta, Carmen; Valerga, Pedro; Verma, Rajnikant; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 79; 5; (2011); p. 1267 – 1275;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1017793-20-2 , The common heterocyclic compound, 1017793-20-2, name is 2,5-Difluoro-4-iodopyridine, molecular formula is C5H2F2IN, 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 Example 5A (100 mg, 0.234 mmol) and 2,5-difluoro-4-iodopyridine (200 mg, 0.830 mmol) in 3.5 mL of 1 ,2-dimethoxyethane was added 1.5 mL saturated sodium bicarbonate solution and the mixture was degassed with nitrogen. 1 , 1 ‘-Bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (33.9 mg, 0.041 mmol) was added and the mixture was heated at 100C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The combined organic layers were washed with water and brine (25 mL each) and dried over sodium sulfate. Filtration, concentration and purification by column chromatography (silica gel, 50% ethyl acetate-hexane) afforded the title compound. LCMS: 415.4 (M+H)+.

The synthetic route of 1017793-20-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 57266-69-0 ,Some common heterocyclic compound, 57266-69-0, molecular formula is C6H4ClNO2, 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.

3-Chloro-2-picolinic acid (47.3 mg, 0.3 mmol), styrene (33 muL, 0.3 mmol), tert-butyl hypochlorite (68 muL, 0.6 mmol) was weighed into a 25 mL Schlenk reaction flask.Then THF (1 mL) was added and placed in a 25 C oil bath for 6 h. After the reaction,The solvent was removed under reduced pressure, using petroleum ether / ethyl acetate as eluent,The yield of the product was 63%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57266-69-0, its application will become more common.

Reference:
Patent; Dalian University of Technology; Feng Xiujuan; Zhang Xitao; Bao Ming; Yu Xiaoqiang; Zhang Sheng; (24 pag.)CN110105270; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1060812-84-1 ,Some common heterocyclic compound, 1060812-84-1, molecular formula is C7H5BrN2, 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 solution mixture of 5-bromopyrazolo[1 ,5-a]pyridine 94-2 (900 mg, 4.59 mmol) and tBuONa (661 .2 mg, 6.88 mmol) in toluene (10 mL) was degassed with argon for about 10 mm. To this mixture were added Pd2(dba)3 (84 mg, 0.091 mmol), BINAP (114.2 mg, 0.lO2mmol) and cyclopropylamine (2 mL, 28.87 mmol) under argon atmosphere. The resulting reaction mixture was maintained at 90C for 2 h under microwave irradiation. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was washed with water (30 mL), brine (25 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography over silica-gel (100-200 mesh) using a solvent gradient of 25% ethyl acetate in pet-ether to afford 500 mg (62%) of N-cyclopropylpyrazolo[1,5-a]pyridin-5- amine 147-1 as a brown solid. 1H-NMR (400 MHz, CDCI3): c58.18 (d, J= 7.5 Hz, 1H), 7.78 (d, J= 2.2 Hz, 1H), 6.72 (d, J= 2.6 Hz, 1H), 6.15-6.18 (m, 2H), 4.28 (5, 1H), 2.44-2.49 (m, 1 H), 0.78-0.80 (m, 2H), 0.54-0.58 (m, 1 H). ESI-LC/MS: m/z 173.75 (M+H); R =1 .99 mm [Waters Acquity UPLC with Quattro-micro detector; Waters Acquity BEH Cl 8,1.7 pm, 2.1 X 50 mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) hold for 0.5 mm and to 10:90 H20 (0.025% TEA):CH3CN (0.025% TEA) in 3.5 mm and hold for 1 .5 mm with flow rate of 0.4 mLlmin].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060812-84-1, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; KONDREDDI, Ravinder Reddy; LEONG, Seh Yong; MISHRA, Pranab Kumar; MOREAU, Robert Joseph; ROLAND, Jason Thomas; SIM, Wei Lin Sandra; SIMON, Oliver; TAN, Liying Jocelyn; YEUNG, Bryan KS; ZOU, Bin; BOLLU, Venkatataiah; WO2014/78802; (2014); 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.10177-29-4, name is 4-Chloronicotinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.5545, as common compound, the synthetic route is as follows.Recommanded Product: 4-Chloronicotinic acid

A mixture of amine 4 (1eq.), carboxylic acid (1.2 eq.), diisopropylethylamine (DIEA) (1.5 eq.), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimidehydrogen chloride (EDC·HCl) (1.2 eq.) in dichloromethane was stirred at room temperature for18 h. The reaction mixture was diluted with dichloromethane and washed withwater and brine. The organic layer was dried over MgSO4 andconcentrated. The crude product was purified by normal phase column chromatography(SP1, Biotage) to yield compound 5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10177-29-4, 4-Chloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Article; Hwang, Jong Yeon; Smithson, David C.; Holbrook, Gloria; Zhu, Fangyi; Connelly, Michele C.; Kaiser, Marcel; Brun, Reto; Kiplin Guy; Bioorganic and Medicinal Chemistry Letters; vol. 23; 14; (2013); p. 4127 – 4131;,
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 1017789-38-6, name is tert-Butyl (4,6-dichloropyridin-2-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C10H12Cl2N2O2

1017789-38-6) (200 mg, 0.760 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (348 mg, 1.67 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.076 mmol), and potassium phosphate tribasic (484 mg, 2.28 mmol) in a flask was evacuated and backfilled with argon three times. Dioxane (3 mL) and water (0.33 mL) were added, and the reaction mixture was heated to 100C for 5 hours. The mixture was allowed to cool to room temperature. Hydrochloric acid (4.0 N in dioxane, 3.80 mL, 15 mmol) was added to the mixture, and the suspension was stirred vigorously for 14 hours at room temperature. The mixture was filtered and concentrated under reduced pressure. The residue was dissolved in DMSO and purified via reverse phase HPLC (15-50% acetonitrile/water with 0.1% TFA, linear gradient) to give 4,6-bis(l -methyl- lH-pyrazol-4-yl)pyridin-2-amine. MS ESI calc’d. for C13H15N6 [M + H]+ 255, found 255. 1H NMR (500 MHz, DMSO-d6) delta 8.46 (s, 1H), 8.42 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.70-7.59 (m, 2H), 7.40 (s, 1H), 6.80 (s, 1H), 3.93 (s, 3H), 3.90 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1017789-38-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DONOFRIO, Anthony; ELLIS, John Michael; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; WO2013/52393; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem