Pyridine-derivatives

Application of 98198-48-2, 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. 98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine, molecular formula is C6H7BrN2, 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.

To a stirred solution of 5-bromo-4-methylpyridin-2-amine (1.0 g, 5.35 mmol) in DMF (25.0 mL) at 0 C was added portion wise NCS (1.428 g, 10.69 mmol). The mixture was stirred at room temperature for 5 h. The reaction was quenched with cold water. The reaction mixture was diluted with ethyl acetate and the layers were separated. The aqueous layer was extracted with ethyl acetate (2 x 50 mL), the combined organic layers was washed with water (50 mL), brine (10 mL), dried over sodium sulphate and concentrated to get crude material. The crude material was purified by ISCO using silica column 40 g silica column. The compound was eluted in 25% ethyl acetate in hexanes, the fractions was collected and concentrated to afford 5-bromo-3-chloro-4-methylpyridin- 2-amine (0.700 g, 3.16 mmol, 59% yield) as a light brown solid. MS (M+1) m/z: 222.9 (MH+). LC retention time 1.14 min [L].

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 98198-48-2, 2-Amino-5-bromo-4-methylpyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; SHERWOOD, Trevor C.; GILMORE, John L.; HAQUE, Tasir Shamsul; WHITELEY, Brian K.; TORTOLANI, David R.; POSY, Shoshana L.; MACOR, John E.; LOMBARDO, Louis J.; SISTLA, Ramesh Kumar; REDDY, Anupama Kandhi Ramachandra; HEGDE, Subramanya; PASUNOORI, Laxman; KUMAR, Sreekantha Ratna; (388 pag.)WO2019/99336; (2019); A1;,
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. 100-26-5, name is 2,5-Pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2,5-Pyridinedicarboxylic acid

A mixture of TbCl3·6H2O (0.0373 g, 0.10 mmol), CuCl2·2H2O (0.0171 g, 0.10 mmol), H2pydc (0.0419 g, 0.25 mmol), NaOH (0.0020 g, 0.50 mmol), and H2O (6 mL) was sealed in a 10-mL Teflon-lined stainless steel container and heated at 170 C for 3 day. Upon being cooled to room temperature at a rate of 5 C/h, dark-blue block crystals were obtained in 43% yield (based on Cu). Anal. for C42H50N6O40Cu3Tb2 (%): C, 28.22; H, 2.82; N, 4.70. Found: C, 28.33; H, 2.74; N, 4.77. IR (solid KBr pellet, cm-1): 3399(m), 1638(s), 1610(s), 1554(s), 1456(m), 1394(s), 1352(s), 1276(m), 1171(w), 1150(w), 1039(w), 892(w), 823(m), 767(m), 691(m), 670(m), 510(m), 454(w).

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, 100-26-5, 2,5-Pyridinedicarboxylic acid.

Reference:
Article; Xia, Zheng-Qiang; Wei, Qing; Chen, San-Ping; Feng, Xin-Ming; Xie, Gang; Qiao, Cheng-Fang; Gao, Sheng-Li; Zhang, Guo-Chun; Journal of Solid State Chemistry; vol. 197; (2013); p. 489 – 498,10;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13362-28-2, 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 13362-28-2 as follows.

The starting material was prepared as follows: (2S,4S)-1-(4-Nitrobenzyloxycarbonyl)-4-acetylthiocarboxypyrrolidine (1.5 g, 4 mmol) was treated at ambient temperature, for 5 hours, with thionyl chloride (12 ml) and a catalytic amount of DMF (15 mg). The solvent was evaporated, the residue taken up in CH2 Cl2, evaporated, dried under reduced pressure for 1 hour and solubilized in CH2 Cl2 (10 ml). This solution was added to a cold (0 C.) solution of 2-amino-4-carboxypyridine (560 mg, 4 mmol) diisopropylethylamine (2.12 ml, 12 mmol) and trimethylsilylchloride (1 ml, 12 mmol) in dry CH2 Cl2. After 12 hours at ambient temperature, the solvent was evaporated, the residue purified by subjecting to chromatography on HP20SS resin, (eluant: CH3 CN/H2 O) to give (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(4-carboxy-2-pyridylcarbamoyl)pyrrolidin-4-ylthioacetate (650 mg, 32.5%). NMR: delta1.9 (m, 1H); 2.32 (s, 3H); 2.83 (m, 1H); 3.36 (m, 1H); 4.0 (m, 2H); 4.64 (s, 1H); 4.9-5.35 (m, 2H); 7.4-7.7 (m, 3H); 7.92 (s, 1H); 8.2 (s, 1H); 8.47 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13362-28-2, its application will become more common.

Reference:
Patent; Zeneca Limited; US5444057; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1034921-05-5, Methyl 4-chloro-3-fluoropicolinate, 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 Methyl 4-chloro-3-fluoropicolinate, blongs to pyridine-derivatives compound. Safety of Methyl 4-chloro-3-fluoropicolinate

A. Synthesis of 3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinic acid To a suspension of N-(4-methylpyridin-2-yl)-5-thiocyanatothiazol-2-amine (3.4 g, 13.69 mmol, described in the synthesis of thiocyanates, Example C) in methanol (150 mL, previously bubbled with argon) was added dithiothreitol (3.70 g, 23.96 mmol). The reaction was stirred at 23 C. for 10 minutes, then methyl 4-chloro-3-fluoropicolinate (2.27 g, 11.98 mmol) was added followed by an aqueous solution of NaOH (1N, 12 mL, 11.98 mmol). The resulting reaction mixture was stirred for 1 hour, then concentrated to about one-fourth of the volume. The mixture was then diluted with water (200 mL) and neutralized with ammonium chloride. The resulting solid was collected by filtration and vacuum dried to give the crude title material (5.7 g) as a solid. This solid was purified on silica gel Biotage chromatography (ethyl acetate) to give the title material (3.01 g, 70%) as a solid. 1H NMR of the compound showed contamination with dithiothreitol. The compound was used as such in the next reaction. The solid was dissolved in THF (100 mL) and the solution was treated with aqueous sodium hydroxide (1N, 12 mL, 11.95 mmol). The reaction was stirred at 23 C. for 2 hours, then diluted with water and neutralized with 1N aq. HCl. The mixture was concentrated to remove THF and the resulting off-white solid was collected by filtration and vacuum dried to give the title material (1.86 g, 64%) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm: 2.31 (3H, s), 6.67-6.73 (1H, m), 6.84 (1H, d, J=4.55 Hz), 6.92 (1H, s), 7.74-7.78 (1H, m), 8.04 (1H, d, J=4.29 Hz), 8.17 (1H, t, J=4.55 Hz).

The synthetic route of 1034921-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; US2010/48581; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 166526-03-0, Adding some certain compound to certain chemical reactions, such as: 166526-03-0, name is 4,6-Dichloronicotinonitrile,molecular formula is C6H2Cl2N2, 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 166526-03-0.

A mixture of 4,6-dichloronicotinonitrile (100 mg, 0.58 mmol), 2-fluoro-5-methoxy-N-(4- (4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide (259 mg, 0.636 mmol), Pd(dppf)C12DCM (24 mg, 0.024 mmol) and Cs2CO3 (381 mg, 1.16 mmol) in dioxane (3 mL) and H20 (0.5 mL) was heated under N2 at 100 C for 6 h. The mixture was cooled to room temperature, diluted with EtOAc (30 mL), filtered through celite, concentrated and purified by silica gel chromatography eluting with ethyl acetate in hexane (0-30 percent) to afford the title compound (244 mg, yield: 100%).

According to the analysis of related databases, 166526-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEW ERA PHARMA, INC.; XIAN, Jun; (82 pag.)WO2018/106459; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 870997-85-6, 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 870997-85-6, name is 3-Amino-5-bromopyridine-2-carboxylic Acid. This compound has unique chemical properties. The synthetic route is as follows.

Example B5, Step 2. A solution of the starting material (e.g., 7-methoxy-2-oxa-6- azaspiro[3.4]oct-6-ene, 1 equiv) and 3-amino-5-bromopicolinic acid (1.5 equiv) in toluene (0.02 M) was refluxed under nitrogen atmosphere until the reaction was complete. After concentration, the residue was purified by silica gel chromatography to give the desired product (e.g., 6′-bromo-l’H-spiro[oxetane-3,2′-pyrrolo[2,l- 6]quinazolin]-9′(3’H)-one).

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 870997-85-6, 3-Amino-5-bromopyridine-2-carboxylic Acid.

Reference:
Patent; HEFFERNAN, Michele, L., R.; HARDY, Larry, Wendell; WU, Frank, Xinhe; SARASWAT, Lakshmi, D.; SPEAR, Kerry, L.; WO2012/170845; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 867267-24-1 ,Some common heterocyclic compound, 867267-24-1, molecular formula is C7H9NO2, 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.

66.9 g (661.1 mmol) of A/A-diisopropylamine were dissolved in 380 g of THF and cooled to a temperature of -60C. 395.2 mL (632.4 mmol) of w-butyllithium (1.6 M in hexane) were added within 45 min while keeping the temperature below -50C. The mixture was stirred at -60C for another 15 min. Then 80 g (574.9 mmol) of 2,5-dimethoxypyridine were added within 45 min while keeping the temperature between -50 and -60C. After completion of the addition the adding funnel was washed with another 10 mL of THF. The reaction mixture was stirred at -60C for 2 h, before 118.9 g (632.4 mmol) triisopropyl borate was added within 30 min. Again the adding funnel was washed with 10 mL of THF. The reaction mixture was warmed to 20C and stirred for 30 min. Then a mixture of acetic acid (106 g) and water (602 g) was added within 15 min and the mixture was stirred for another 30 min. Then the organic solvents (650 g) were evaporated in vacuo (300 mbar) at a temperature of maximum 70C and the resulting suspension cooled to 20C and filtered. The product cake was washed with cold water (three times 100 mL) and dried at 40C for about 16 hours under reduced pressure in a drying oven. Yield: 78.6 g (75% of theory). MS (ESI+): m/z = 184.1 [M+H]+ ; ‘H-NMR (400MHz, DMSO-cL): d [ppm] = 8.15 (hr s, 2H), 7.80 (s, 1H), 6.76 (s, 1H), 3.78 (d, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,867267-24-1, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; EGGER, Julian; GOeTZ, Daniel; SOWA, Michal; (43 pag.)WO2019/175043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 76006-08-1, 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 76006-08-1 as follows.

To the solution of 5-chloro-lH-pyrazolo[3,4-c]pyridine (0.300 g, 1.95 mmol) in DMF (5 mL) at 0C was added NaH (0.234 g, 5.86 mmol, 60% dispersion in oil). After stirring for 5 min. tetrahydro-2H-pyran-4-yl methanesulfonate (0.632 g, 3.5 mmol) was added and the reaction mixture was heated at 100C for 5 h. TLC analysis indicated complete consumption of starting material and formation of 2 new spots. The reaction mixture was quenched by slow addition of ice-cold water (3 mL). The residue was bi-phased with water (15 mL) and ethyl acetate (25 mL). The aqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine (1 x 15 mL), dried (anh. Na2S04) and concentrated under reduced pressure to furnish the title compound (0.230 g.). (0881) In step-1, the non-polar spot amongst the two new spots in the TLC, was the required regio-isomer (5). Both the regio-isomers obtained during N-alkylation were purified by flash column chromatography and the structure was confirmed by NMR and NOE experiments. MS (EI) calc’d for CnHi2N3OCl [M+H]+ Expected: 238; Found: 238; 1H NMR (400 MHz, CDC13) delta 9.06 (s, 1H), 8.15 (s, 1H), 7.79 (s, 1H), 4.90-4.78 (m, 1H), 4.24 (dd, 2H, J7 = 3.6 Hz, J2 = 11.2 Hz), 3.76-3.64 (m, 2H), 2.52-2.37 (m, 2H), 2.06 (dd, 2H, J7 = 2.4 Hz, J2 = 12.8 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76006-08-1, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SILIPHAIVANH, Phieng; METHOT, Joey; LIPFORD, Kathryn Ann; MOLINARI, Danielle; SLOMAN, David, L.; WITTER, David; ZHOU, Hua; BOYCE, Christopher; HUANG, Xianhai; LIM, Jongwon; GUERIN, David; KARUNAKARAN, Ganesh Babu; BAKSHI, Raman Kumar; LIU, Ziping; FU, Jianmin; WAN, Zhilong; LIU, Wei; (216 pag.)WO2016/100050; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17997-47-6, 2-(Tributylstannyl)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, Application In Synthesis of 2-(Tributylstannyl)pyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-(Tributylstannyl)pyridine

A mixture of (S)-2-( 1 -(2-chloro-7-fluoroquinolin-3 -yl)ethyl)isoindoline- 1,3 -dione (85.6 g, 241 mmol), Pd(PPh3)4 (14 g, 12.1 mmol, 0.O5eq) and 2-(tributylstannyl)pyridine (107 g, 289 mmol, 1.2 eq) in dioxane (3.0 L) was heated to 90 C under N2 overnight, then heated to 101 C for additional 2 days. The reaction mixture was cooled to room temperature, decanted and the final 200 mL solution was filtered. The combined solvents were concentrated to 300 mL and filtered to give a tan solid, which was washed with EtOAc/hexane (1/1) and dried (82.1 g). The mother liquor was concentrated to 100 mL and treated with EtOAc/hexane, 1/1 (200 mL) to give additional 2.2 g tan solid, overall 84.3 g.

The synthetic route of 17997-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; KELLY, Ron, C.; WORTMAN, Sarah; WO2015/171725; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 875781-15-0, 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. 875781-15-0, name is 5-Bromo-2-fluoronicotinaldehyde, molecular formula is C6H3BrFNO, 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.

Into two parallel 30 ml sealed tubes, each was placed 5-bromo-2-fluoronicotinaldehyde (1.83 g, 9.0 mmol), allylamine (1.03 g, 18.0 mmol) and ethanol (15 mL). The resulting solution was stirred for 3 h at 80 C. After cooling room temperature, the resulting solution was poured into 30 mL of hydrochloric acid (iN) and the resulting mixture was stirred for 10 mm and then extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Purification by silica gel chromatography (eluting with 1:10 EtOAc/pet. ether) afforded 2-(allylamino)-5-bromonicotinaldehyde as a light yellow solid. MS: (ESI, m/z): 241, 243 [M+H].

According to the analysis of related databases, 875781-15-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem