Category: pyridine-derivatives

Related Products of 135900-33-3, Adding some certain compound to certain chemical reactions, such as: 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine,molecular formula is C6H5F3N2O, 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 135900-33-3.

[0293] Compound Int-5 (Example 122) (90 mg, 0.43 mmol, 1.0 eq) and 6- (trifluoromethoxy)pyridin-3-amine (84 mg, 0.47 mmol, 1.1 eq) were dissolved in DMF (3 mL), and the resulting mixture was cooled down to 0 C. Then HATU (181 mg, 0.47 mmol, 1.1 eq) and DIPEA (0.16 mL, 0.868 mmol, 2.0 eq) were added to the reaction mixture at 0 C. The reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 3 hrs. The progress of the reaction was monitored by LCMS and TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water. The formed solid was filtered, washed and dried in vacuo to give 40 mg of the desired compound 128 as an off-white solid in 25% yield. 1H NMR (400 MHz, DMSO-de): delta 11.12 (s, 1H), 9.03-9.02 (dd, J = 4.4 Hz, 2.0 Hz, 1H), 8.68-8.69 (d, J = 2.4 Hz, 1H), 8.46-8.44 (d, J = 7.6 Hz, 1H), 8.39-8.36 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.30-8.31 (m, 2H), 7.70- 7.67 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.39-7.37 (d, J = 8.8 Hz, 1H). 99.45% purity by LCMS; m/z =368.11 [M+H]+.

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. 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1196157-14-8, 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. 1196157-14-8, name is 4-Bromo-5-methylpicolinaldehyde. A new synthetic method of this compound is introduced below.

To a solution of a 60% dispersion of NaH in mineral oil (0.29 g, 7.25 mmol) in DME (2 niL) at – 30 C was added a solution of ethyl 2-phosphonoacetate (1.46 mL, 7.29 mmol) in DME (13 mL), and the mixture was stirred at this temperature for 30 min. To this solution was added a solution of 4-bromo-5-methylpyridine-2-carbaldehyde (64) (1.32 g, 6.60 mmol) in DME (3 mL), and the reaction was stirred at -30 C for 1.5 h and then poured into water (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated NH4CI solution and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, ethyl acetate:hexanes 1 :9) to give 65 (1.553 g, 87%) as a colorless crystalline solid: ? NMR (400 MHz, CDCI3) ? 8.41 (s, 1H), 7.59 (d, J= 15.6, 1H), 7.58 (s, 1H), 6.88 (d, J= 15.6, 1H), 4.25 (q, J= 7.2, 2H), 2.38 (s, 3H), 1.31 (t, J= 7.2, 3H); 13C NMR (100.6 MHz, CDC13) ? 166.4, 151.6, 150.8, 141.6, 135.4, 134.7, 127.3, 122.9, 60.6, 19.4, 14.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1196157-14-8, 4-Bromo-5-methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA ACTING FOR AND ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl, E.; JURUTKA, Peter, W.; MARSHALL, Pamela, A.; WO2013/40227; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1122-43-6, 2,6-Dimethyl-3-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, 1122-43-6, blongs to pyridine-derivatives compound. Safety of 2,6-Dimethyl-3-hydroxypyridine

To a solution of 2,6-dimethyl-3-pyridinol (3 g, 24.35 mmol) in THF (30 ml) at r.t., were added Cs2CO3 (15.87 g, 48.71 mmol) and 3,4-difluoro-l-nitro-benzene (3.87 g, 24.35 mmol). The reaction mixture was heated at reflux for 2 h. After cooling to r.t. the solids were filtered off and the filtrate was evaporated to dryness. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D21 (5.88 g, 92 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; ADDEX PHARMA S.A.; CID-NUNEZ, Jose, Maria; DE LUCAS OLIVARES, Ana, Isabel; TRABANCO-SUAREZ, Andres, Avelino; MACDONALD, Gregor, James; WO2010/130423; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52311-50-9, 2-Chloro-4-ethoxypyridine, 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: 52311-50-9, blongs to pyridine-derivatives compound. SDS of cas: 52311-50-9

To a degassed mixture of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide ( 9.4g, 38 mmol) and 2-chloro-4-ethoxypyridine ( 5g, 31.7 mmol) in dioxane was added Brettphos-prePd (catalytic amount) and CS2CO3 (12.3 g, 37.8 mmol) under N2 atmosphere. The mixture was heated to 100 C and stirred for 3.5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified on silic-gel (PE: EA = 100% ~ 30%) to give N-(4- ethoxypyridin-2-yl)-4-(4,4, 5, 5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)benzamide (8.8 g, yield 75%). 1HNMR (400MHz, CDC13): 5=8.74 (s, 1 H), 8.05-8.02(m, 1 H), 8.01 (s, 1 H), 7.94-7.89 (m, 4 H), 6.60-6.59 (m, 1 H), 4.20-4.14 (m, 2 H), 1.47-1.43 (m, 3 H), 1.36 (s, 12 H), MS (ESI): M/Z (M+l)=369.19.

The synthetic route of 52311-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 887266-57-1, Adding some certain compound to certain chemical reactions, such as: 887266-57-1, name is 3-Fluoro-2-hydrazinylpyridine,molecular formula is C5H6FN3, 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 887266-57-1.

Under argon, a solution of methyl 2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2- hydroxypropyl] -4,5-dihydro- lH-l,2,4-triazol-1-yl}ethanimidate (Example 2A, 150 mg, 396 muiotaetaomicron) in THF (1.5 ml) was treated at 0C with N,N-diisopropylethylamine (210 mu, 1.2 mmol) and (2S)-1- chloro-1-oxopropan-2-yl acetate (55 mu, 440 muiotaetaomicron) and stirred at 0C for 30 min. 3-Fluoro-2- hydrazinylpyridine (55.4 mg, 436 muiotaetaomicron) was then added and the resulting mixture was stirred overnight at room temperature and evaporated. The residue was purified by preparative HPLC (Method 4) affording 152 mg (67% of th.) of the title compound.LC-MS (Method 1): Rt = 1.01 min; MS (ESIpos): m/z = 570 [M+H]+ -NMR (400 MHz, DMSO-d6) delta [ppm]: 8.46 (br. d, 1H), 8.23-8.05 (m, 1H), 7.88-7.53 (m, 5H), 6.89 (d, 1H), 5.93 (q, 1H), 5.12 (m, 2H), 4.30 (m, 1H), 4.08-3.71 (m, 2H), 1.79 (s, 3H), 1.59 (d, 3H).

According to the analysis of related databases, 887266-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; TINEL, Hanna; SCHMECK, Carsten; WASNAIRE, Pierre; SCHIRMER, Heiko; LUSTIG, Klemens; GRIEBENOW, Nils; (195 pag.)WO2019/81302; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-52-4, 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. 884494-52-4, name is 3-Bromo-2-fluoro-4-iodopyridine. A new synthetic method of this compound is introduced below.

In a dry 3 neck 2 L flask equipped with a dry addition funnel, thermometer and stir bar was added 3- bromo-2-fluoro-4-iodopyridine (83.4 g, 276 mmol) followed by 300 mL of anhydrous THF under an atmosphere of nitrogen. The solution was cooled to -7O0C in 2-propanol/dry ice bath. A solution of isopropylmagnesium chloride 2.0 M in diethyl ether (145 mL, 290 mmol) was added drop wise over a period of 30 minutes. The solution was then stirred for 30 minutes before zinc (II) chloride 0.5 M in THF (276 mL, 138 mmol) was cannulated in. The solution was warmed to room temperature and stirred for lhour. The addition funnel was replaced with a reflux condenser and N4-cyclopentyl-5-iodopyrimidine-2,4-diamine (243, see example 200) (28.00 g, 92.1 mmol) was added, followed by Pd(PPh3)4 (5.32 g, 4.60 mmol). The solution was heated over night at a gentle reflux. After concentrating the solution to 1/1 Oth of the volume under vacuum, it was cooled in an ice bath. To this was added 100 mL of cold saturated NH4Cl, followed by 500 mL of water. 50OmL of 12% isopropanol/DCM was then added and the solution was stirred at room temperature for lhour before being filtered through filter paper. The filter cake was washed in succession with water, DCM and 12% 2-propanol /DCM. The filtrate was partitioned in a separation runnel and the aqueous layer was washed with 12% 2-propanol /DCM. The organics were dried over MgSO4 and then concentrated under vacuum. The residue obtained was partially dissolved in DCM with sonication and filtered off to give compound 244 (26.45g, 81.6%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta ppm 8.18 (1 H, d, J= 4.9 Hz), 7.52 (1 H, s), 7.26 (1 H, dd, J= 4.9, 0.7 Hz), 6.34 (2 H, s), 6.12 (1 H, d, J= 7.6 Hz), 4.42 (1 H, sxt, J= 7.4 Hz), 1.76 – 1.96 (2 H, m), 1.55 – 1.68 (2 H, m), 1.31 – 1.53 (4 H, m) ) ppm; LCMS-ESI (POS), M/Z, M+l : Found 352.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-52-4, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); 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 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 1149-24-2

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

With the rapid development of chemical substances, we look forward to future research findings about 1149-24-2.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below., SDS of cas: 709652-82-4

Boronate 10: Compound 9 (50 g, 0.224 mol), bis(pinacolato)diboron (85.6 g, 0.337 mol), KOAc (44.1 g, 0.449 mol) and Pd(dppf)Cl2.CH2Cl2 (2.77 g, 3.4 mmol) were charged into a flask. Dioxane (400 mL) was added. The reaction mixture was stirred at 100 C. for 2 hr under Ar. When LC-MS indicated that the reaction was completed, the mixture was cooled to room temperature. The mixture was filtered through diatomite, concentrated, diluted with a mixture of ethyl acetate and hexane in 3/1 ratio (1000 mL), filtered through silica gel (300-400 mesh), concentrated, crystallized and dried to give boronate 10 (32 g, 66%) as a white solid.

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, 709652-82-4, 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; US2014/179675; (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.116026-95-0, name is tert-Butyl (4-formylpyridin-3-yl)carbamate, molecular formula is C11H14N2O3, molecular weight is 222.24, as common compound, the synthetic route is as follows.Computed Properties of C11H14N2O3

Step 2, Method 8: tert-But l iV-[4-(6-Methoxy-l,3-benzothiazol-2-yl)pyridin-3- yl] carbamate[0172] To a stirred solution of 2-[(2-amino-5-methoxyphenyl)disulfonyl]-4- methoxyaniline (100 mg, 0.324 mmol) and te^butyl(4-formylpyridin-3-yl)carbamate (144 mg, 0.648 mmol) in N,N-dimethylformamide (3 mL) under nitrogen was added sodium metabisulfite (123 mg, 0.648 mmol). The reaction mixture was heated to 130 C and stirred for 1.5 hours. The mixture was allowed to cool to room temperature then ethyl acetate (10 mL) and water (10 mL) added and thelayers separated. The organic layer was washed with water (2 x 10 mL) and brine (2 x 10 mL). The combined organic layers were dried over magnesium sulphate, concentrated, recrystallised twice from methanol (8 mL) and the resulting solid dried under suction to give the title compound 50 mg (21% yield) as an off-white powder. 5H NMR (500 MHz, DMSO) 10.76 (s, 1H), 9.32 (s, 1H), 8.43 (d, J = 5.1 Hz, 1H), 7.98 (d, J = 9.0 Hz, 1H), 7.89 (d, J = 5.1 Hz, 1H), 7.82 (d, J = 2.5 Hz, 1H), 7.22 (dd, J = 9.0, 2.5 Hz, 1H), 3.88 (s, 3H), 1.49 (s, 9H). Tr(MET-uHPLC-AB-lOl) = 4.1 min, (ES+) (M+H)+358.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116026-95-0, tert-Butyl (4-formylpyridin-3-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; BROWN, Christopher, John; PRIME, Michael, Edward; WEDDELL, Derek, Alexander; WALTER, Daryl, Simon; GILES, Paul, Richard; WIGGINTON, Ian, James; TAYLOR, Malcolm, George; GALAN, Sebastien, Rene, Gabriel; JOHNSON, Peter, David; KRUeLLE, Thomas, Martin; MORAO, Inaki; CLARK-FREW, Daniel; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; (120 pag.)WO2016/33460; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109613-97-0, 2-Bromo-4-methoxypyridin-3-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, 109613-97-0, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-4-methoxypyridin-3-amine

To a solution of 2-bromo-4-methoxypyridin-3-amine (2.1 g, 10.34 mmol), N-(4-ethynylpyridin-2-yl)acetamide (1.82 g, 11.38 mmol) in DMF (15 mL) was added TEA (21.62 mL, 155 mmol) and CuI (0.12 g, 0.62 mmol). The reaction mixture was purged with nitrogen for 2 min, followed by addition of Pd(PPh3)2Cl2 (0.73 g, 1.03 mmol). The reaction mixture was then heated at 100 C. for 3 h. The reaction mixture was cooled down and diluted with ethyl acetate and saturated NaHCO3 solution. The organic layer (two times extracts) were combined, washed with saturated NaHCO3 solution, dried over MgSO4. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography. The product was eluted with DCM to 50% of 10% MeOH in DCM to give the desired product as a light yellow (1.0 g, 34%); HPLC: RT=0.48 min (H2O/ACN with 0.05% TFA, Waters Acquity SDS C18, 2.1×50 mm, 1.7-mum particles, gradient=1.8 min, wavelength=220 nm); MS (ES): m/z=283.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 10.59 (s, 1H), 8.34 (dd, J=5.1, 0.7 Hz, 1H), 8.22 (s, 1H), 7.79 (d, J=5.3 Hz, 1H), 7.34 (dd, J=5.2, 1.4 Hz, 1H), 6.91 (d, J=5.3 Hz, 1H), 5.35 (s, 2H), 4.03 (q, J=7.2 Hz, 1H), 3.88 (s, 3H), 2.11 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109613-97-0, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; Fink, Brian E.; Zhao, Yufen; Borzilleri, Robert M.; Zhang, Liping; Kim, Kyoung S.; Kamau, Muthoni G.; Tebben, Andrew J.; (162 pag.)US2016/176871; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem