Day: February 19, 2021

Application of 80537-07-1, Adding some certain compound to certain chemical reactions, such as: 80537-07-1, name is 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid,molecular formula is C14H10N2O2, 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 80537-07-1.

EXAMPLE 56 STR64 Thionyl chloride (240 mg) was added dropwise to a stirred mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid [compound (I)] (320 mg) and N,N-dimethylformamide (one drop) in chloroform (10 ml), and then stirred under reflux for 4 hours. After cooling the mixture, chloroform was evaporated in vacuo to give acid chloride of compound (I). Triethylamine (338 mg) was added to a suspension of the acid chloride of compound (I) in methylene chloride (10 ml) under ice-cooling, and to this suspension a solution of 2-ethylpiperidine in methylene chloride was added dropwise. The mixture was stirred under ice-cooling and stood at room temperature overnight. Saturated sodium chloride aqueous solution (20 ml) was added to the mixture and extracted with chloroform (20 ml). The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (8 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-(2-phenylpyrazolo[1,5-a]pyridin-3-ylcarbonyl)-2-ethylpiperidine (263 mg). mp: 182-183 C. IR (Nujol): 1630, 1600, 1520 cm-1 NMR (DMSO-d6, delta): 0.69 (3H, t, J=7.0 Hz), 1.12-1.93 (8H, m), 2.73-3.17 (1H, m), 3.69-4.45 (2H, m) 7.07 (1H, td, J=7.0 Hz and 2.0 Hz), 7.29-8.00 (7H, m), 8.86 (1H, dd, J=7.0 Hz and 1.0 Hz) Analysis Calcd. for C21 H23 N3 O: C 75 65, H 6.95, N 12.60. Found: C 75.75, H 7.01, N 12.66.

According to the analysis of related databases, 80537-07-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4994453; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-10-3, 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 63071-10-3 as follows.

[0360] A suspension OfMnO2 (7.3 g, 84 mmol) and (4-chloro-pyrindin-2-yl)methanol(1 g, 7 mmol) in CHCl3 was heated to refulx for 90 minutes. The mixture was filtered though a layer of Celite and concentrated in vacuo to afford 520 mg of 4-chloropicolinaldehyde as a white solid. HPLC 1.8 minutes and MS 142 as M=I peak.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63071-10-3, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/106139; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 148493-37-2, 2,6-Dichloro-3-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, COA of Formula: C5H2Cl2IN, blongs to pyridine-derivatives compound. COA of Formula: C5H2Cl2IN

General procedure: To asolution of 3-bromo-2,6-dichloropyridine (4.70 g, 20.7 mmol) in DMSO (103 ml)was added cesium fluoride (12.6 g, 82.9 mmol) at room temperature. The mixturewas stirred at 80 C under air for 8 h. The mixture was poured into water atroom temperature and extracted with Et2O. The organic layer wasseparated, washed with water and brine, dried over Na2SO4and concentrated in vacuo. (400 Torr, 40 C). The residue was purified bycolumn chromatography (silica gel, eluted with EtOAc in hexane) to give 3-bromo-2,6-difluoropyridine (3B) (2.58 g, 64%) as colorless oil. 1H NMR (CDCl3)delta: 6.79 1H,dd, J = 8.3, 3.0 Hz), 8.03 (1H, ddd, J = 8.4, 8.4 7.0 Hz). 19F NMR(CDCl3) delta: -69.3 Hz, -63.8 Hz. The compound 4B-8B were prepared in a manner similarto that described for 3B.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,148493-37-2, 2,6-Dichloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Article; Katoh, Taisuke; Tomata, Yoshihide; Tsukamoto, Tetsuya; Nakada, Yoshihisa; Tetrahedron Letters; vol. 56; 44; (2015); p. 6043 – 6046;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 944937-53-5, 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. 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. A new synthetic method of this compound is introduced below.

A solution of 6-bromo-1H-pyrrolo[3,2-¡ê]pyridine (54 kg from multiple batches based on wt % assay, 274 mol) in ethyl acetate from the previous step was distilled under vacuum at 45¡À5C to a volume of about 110 L (2L/kg) and then cooled to 25¡À5C. Dimethylcarbonate (33.0 kg, 367 mol) and Et3N (22.0 kg, 217 mol) were added and the mixture was distilled under vacuum at 50¡À5 C to a volume of about 85 L. N,N- dimethylformamide (82.5 kg, 1.6L/kg) was added and the mixture was distilled under vacuum at 50¡À5 C until no distillate was observed. The mixture was cooled to 25¡À5C, and dimethylcarbonate (165 kg, 1833 mol), Et3N (60.5 kg, 598 mol), and tetrabutylammonium bromide (11.0 kg) were added. The reaction mixture was heated to 88¡À5C. After 12 hours at 105-110C (jacket temperature), which corresponded to 83-85C reaction mixture temperature, HPLC analysis indicated 59.6% of the starting material remained. The jacket temperature was increased to 115-120C (corresponding to 84-87C reaction mixture temperature). After 18 hours at 115-120C (jacket temperature) HPLC analysis indicated 0.2% of the starting material remained. The mixture was cooled to 25C and then concentrated under vacuum at 55¡À5C to remove most of the dimethylcarbonate and Et3N. Next, the mixture was cooled to 25C and MTBE (340 kg) was added, followed by water (440 kg). The mixture was stirred for 30 minutes. Stirring was stopped and the mixture was left for 30 minutes for phase separation to occur. The aqueous phase was extracted with MTBE (2 x 209 kg). The MTBE phases were combined and washed with brine solution (286 kg). Activated charcoal (2.7 kg) was added to the organic phase, which was stirred for 1 hour and then filtered through a pad of Celite. The filter cake was washed with MTBE (55 kg). The organic layers were combined (750 kg, 6.45%> by HPLC-assay) and distilled to dryness to obtain the title compound as yellow oil (48.4 kg). The product was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,944937-53-5, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHANG, Edcon; NOTZ, Wolfgang Reinhard Ludwig; WALLACE, Michael B.; WO2014/11568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60290-21-3, 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 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 4-chloro-lH-pyrrolo[3,2-c]pyridine ([60290-21-3], 4.74 g, 31.07 mmol) in DMF (72.16 mL) at 0 C was added NaH (60% dispersion in mineral oil, (0187) 1.74 g, 43.49 mmol) and the reaction mixture was warmed to rt and stirred for 30 min. Then the reaction mixture was cooled to 0 C and 2-chloro-N,N-dimethylacetamide ([2675-89-0], 3.83 mL, 37.28 mmol) was added and the reaction mixture was warmed to rt for 2 h. NaHC03 sat. sol. was added and the organic layer was extracted with EtOAc, then washed with water and brine, then dried over MgS04 and solvent was removed. The residue was purified by flash column chromatography (Heptane/EtOAc from 80/20 to 0/100) to obtain 1-1 (6.34 g, yield 68%) as a white solid.

According to the analysis of related databases, 60290-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; LEENAERTS, Joseph, Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; MARTINEZ LAMENCA, Carolina; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (110 pag.)WO2019/243533; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1034467-80-5, 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. 1034467-80-5, name is 5-Cyclopropyl-2-fluoropyridine, molecular formula is C8H8FN, 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.

In a reaction vial designed for microwave heating, 3-cyclopropyl-4-phenoxy-l H- pyrazole (0.16 g, 0.799 mmol), 5-cyclopropyl-2-fluoropyridine (intermediate 50) (0.11 g, 0.799 mmol) and cesium carbonate (0.28 g, 0.878 mmol) were heated in dry acetonitrile (4 mL, dried over 4A molecular sieves) at 160 C for one hour. The resulting was adsorbed over silica and purified by chromatography over silica gel (cyclohexane – ethyl acetate 95/5) to yield the expected compound as an oil (0.2 g, 78 %). 5H (CDCI3): 0.72 (m, 2H); 0.85 (m, 2H); 1.03 (m, 4H); 1.93 (m, 2H); 7.09 (m, 3H); 7.31 (m, 2H); 7.40 (dd, 1H, J = 2.4 and 8.5); 7.80 (d, 1 H, J – 8.5); 8.15 (d, 1H, J – 2.4); 8.27 (s, 1H). 13C (CDC13): 7.0; 7.3; 8.7; 12.6; 11 1 .0; 1 16.2; 1 17.6; 122.5; 129.6; 135.4; 136.3 ; 140.1 ; 146.0; 148.5; 149.7; 158.7. HRMS: Calc. for C20H19N3O + H: 318.1606; Found: 318.1562.

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 1034467-80-5, 5-Cyclopropyl-2-fluoropyridine.

Reference:
Patent; INSTITUT PASTEUR; JANIN, Yves-Louis; GUILLOU, Sandrine; LUCAS-HOURANI, Marianne; MUNIER-LEHMANN, Helene; NOEL, Anne; SALANOUVE, Elise; TANGY, Frederic; VIDALAIN, Pierre-Olivier; WO2015/155680; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 625-92-3, 3,5-Dibromopyridine, 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 3,5-Dibromopyridine, blongs to pyridine-derivatives compound. Quality Control of 3,5-Dibromopyridine

3-(Benzyloxy)-5-bromopyridine [1099] (Zhu. G.-D. et al., Bioorg. Med. Chem. Lett. 2006, 16, 3150-3155) [1100] A 500 mL three-necked flask was charged with sodium hydride (60% dispersion in oil; 9.6 g, 240 mmol, 2.0 equiv.) and fitted out with stir bar, dropping funnel, N2 balloon, and septa. The sodium hydride was washed with hexane (2¡Á150 mL), then anhydrous DMF (110 mL) was added. With stifling and intermittent ice cooling, benzyl alcohol (25 mL, 240 mmol, 2.0 equiv.) was added dropwise within 105 min. The temperature was kept high enough to permit efficient stifling and prevent excessive frothing. After the addition was finished, the dropping funnel was rinsed with anhydrous DMF. Stirring was continued at room temperature for 20 min. The flask was briefly opened to add 3,5-dibromopyridine (28.4 g, 120 mmol) all at once. The atmosphere was again replaced with N2, and the reaction mixture was stirred at room temperature for 15 h. A thin layer chromatogram (small aliquot quenched into EtOAc/H2O; silica gel, EtOAc/hexane 15:85) taken shortly before the end of this period demonstrated the near-absence of starting material (Rf 0.6) and the formation of a product (Rf 0.25); benzyl alcohol was detected at Rf 0.15. The bulk of DMF was distilled in an oil pump vacuum at a bath temperature of 40 C. into a receiver cooled with acetone/dry ice. Initial foaming was due to the evaporation of residual hexane. The receiver was subsequently changed to maintain a high vacuum. The residue was taken up in diethyl ether (300 mL) and the resulting suspension poured into ice water (300 mL). The phases were separated, and the aqueous phase was twice extracted with ether (100 mL each). The combined organic phases were washed with brine (100 mL) and dried over MgSO4 (15 g). Evaporation furnished an orange-colored liquid together with a colorless solid. After transfer into a 200 mL flask, benzyl alcohol was distilled off in an oil pump vacuum into a -78 C. receiver. The product began to crystallize after partial cooling, whereon methanol (60 mL) was added. Crystallization was initially allowed to proceed at room temperature, then in the freezer overnight. [1101] The product was isolated by suction filtration, washed with two portions of freezer-chilled methanol (20 mL each), and dried (40 C./oil pump) to obtain 23.2 g (73%) of light-tan crystals (mp 67-68.5 C.). The mother liquor was concentrated to a few mL, diluted with methanol (15 mL), seeded, and placed in the freezer. Isolation as above gave 1.7 g of a solid which upon TLC examination revealed contamination with polar material. The second mother liquor still contained substantial amounts of benzyl alcohol, which was removed by evaporation into a 50 mL flask and bulb-to-bulb distillation at 80 C. in an oil pump vacuum until by visual appearance no further distillate was formed. The dark residue (2.7 g) together with the impure second crystal fraction was taken up in CH2Cl2 (3 mL) and chromatographed on silica gel (25¡Á3.8 cm, EtOAc/hexane 1:9) to yield, after evaporation and drying, another 2.4 g (8%) of the product 2. 1H NMR (CDCl3, 300 MHz) delta 8.33 (narrow m, 2H), 7.50-7.32 (m, 6H), 5.11 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,625-92-3, 3,5-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; The Board of Trustees of the University of Illinois; PsychoGenics, Inc.; Chandrasekhar, Jayaraman; Kozikowski, Alan P.; Liu, Jianhua; Tueckmantel, Werner; Walker, Joel R.; Yuen, Po-wai; US2013/184313; (2013); 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. 132308-19-1, name is Methyl 5-chloropyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 5-chloropyridine-2-carboxylate

B. Preparation of (5-chloropyridin-2-yl)methanol To a stirring solution of methyl 5-chloropicolinate (1 g, 5.8 mmol) in methanol at room temperature under argon was added sodium borohydride (440 mg, 11.57 mmol). The reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was concentrated under vacuum to obtain a gum. Water (15 mL) and EtOAc (30 mL) were added and the layers were separated. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to obtain 840 mg of the title compound as colorless gum. HPLC/MS: retention time=0.755 min, [M+H]+=144.

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, 132308-19-1, Methyl 5-chloropyridine-2-carboxylate.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1427-06-1, 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 1427-06-1 as follows.

General procedure: A mixture of substituted piperazine, homopiperazine or piperidine (X), methyl 4-fluorobenzoate and K2CO3 in DMSO was refluxed at 120 C for 24 hrs resulting in the formation of an off-white precipitate. The reaction mixture was cooled to room temperature and then poured into a vessel containing water. The mixture was left to stir at room temperature for 30 minutes and the solid was collected via filtration, washed with water and air dried overnight to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1427-06-1, its application will become more common.

Reference:
Article; Jalily, Pouria H.; Eldstrom, Jodene; Miller, Scott C.; Kwan, Daniel C.; Tai, Sheldon S.-H.; Chou, Doug; Niikura, Masahiro; Tietjen, Ian; Fedida, David; Molecular Pharmacology; vol. 90; 2; (2016); p. 80 – 95;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 110919-71-6, Adding some certain compound to certain chemical reactions, such as: 110919-71-6, name is 2-Amino-5-fluoro-6-methylpyridine,molecular formula is C6H7FN2, 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 110919-71-6.

2-amino-5-fluoro-6-methylpyridine (0.559 mmol) and methyl 3-chloro-l-methyl-4-[[(li?)-2,2,2- trifluoro-l-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylate (150 mg, 0.43 mmol) were dissolved in THF (10 mL). Lithium bis(trimethylsilyl)amide (1 M in THF) (1.29 mL, 1 M, 1.29 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was quenched with sat.NH4Cl (aq) (5 mL). The aqueous layer was extracted with CH2C12 (2 X 5 mL). The combined organic layers were evaporated to dryness and the residue was purified on silica using a heptane to EtOAc gradient. The obtained product was crystallized from CH2C12, triturated with diisopropylether and dried, resulting in compound 7 (83 mg) as a white powder. Method D; Rt: 1.96 min. m/z : 441.0 (M-H)” Exact mass: 442.0. 1H NMR (400 MHz, DMSO-d6) 5 ppm 1.19 (d, J=7.0 Hz, 3 H), 2.41 (d, J=2.9 Hz, 3 H), 3.77 (s, 3 H), 3.88 – 4.01 (m, 1 H), 7.65 (s, 1 H), 7.70 (t, J=9.0 Hz, 1 H), 7.98 (dd, J=9.0, 3.1 Hz, 1 H), 8.43 (br. s., 1 H), 10.68 (s, 1 H). MP: 173.1 C.

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. 110919-71-6, 2-Amino-5-fluoro-6-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem