Category: pyridine-derivatives

Related Products of 55899-13-3 ,Some common heterocyclic compound, 55899-13-3, molecular formula is C14H17BrN2O3S, 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.

The reaction was performed using general flow procedure reacting 3-bromopyridine 2a with ethylpropiolate 4b. The outlet solution (195 mL, collected over 51 mins) was stirred at room temperature whiletriethylamine (17.5 mL, 126 mmol) was added followed by ethyl propiolate (9.30 mL, 98.4 mmol). The bright redmixture was stirred at room temperature for 15 minutes was concentrated in vacuo to remove the MeCN and thendiluted with EtOAc (250 mL) and brine (100 mL). The organic layer was separated and the aqueous phase washedtwice more with EtOAc (2 x 200 mL). The combined organic layers were dried over anhydrous sodium sulfate andconcentrated in vacuo to give a dark red oil.The crude material was purified by column chromatography on a 100 g silica column using the Biotage machine anda gradient from 7 to 60 % EtOAc/heptane. 5c eluted first from the column. Pale red solid (1.94 g, 51 min collectiontime, 11 %). 1H NMR (400 MHz, d6-DMSO) (3H, t, J = 4 Hz, CH2CH3), 4.31 (2H, q, J = 4 Hz, CH2CH3), 7.743 SYNLETT: LETTERTemplate for SYNLETT and SYNTHESIS Thieme Stuttgart · New York 2017-04-25 page 3 of 4(1H, d, J = 8 Hz, ArH), 8.01 (1H, d, J = 4 Hz, ArH), 8.47 (1H, s, ArH), 9.31 (1H, s, ArH) ppm. 13C NMR (101 MHz,d6-DMSO) 14.3, 59.8, 103.6, 108.1, 118.9, 130.3, 131.3, 138.6, 144.7, 162.2 ppm. HRMS (FAB) calcd forC10H10O2N2Br 268.99202, found 268.99194/270.98981

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. 55899-13-3, 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Brocklehurst, Cara E.; Koch, Guido; Rothe-Poellet, Stephanie; La Vecchia, Luigi; Synlett; vol. 28; 13; (2017); p. 1636 – 1640;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53554-20-4, 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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile, molecular formula is C6H4ClN3, 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.

A mixture of NMP (8mL), I2 (82.6mg, 0.33mmol), and Zn (809mg, 12.4mmol) was stirred at rt until the red colour of I2 disappeared (ca. 4min). Butyl-1-bromide (0.88mL, 8.14mmol) was added and the mixture was stirred at 80C for 3h. The mixture was cooled to rt and 38 (1.00g crude, max. 4.30mmol) and Pd2(PPh3)4 (150mg, 0.13mmol) were added, and the reaction mixture was stirred at rt for 1h. Sat. aq. NH4Cl (120mL) was added, and the mixture was extracted with EtOAc (2×120mL). The combined organic phase was washed with brine (120mL), dried over Mg2SO4, and evaporated under vacuum. Purification by FC (heptane/EtOAc 100:0 to 0:100) afforded the product with small impurities as light yellow solid (225mg, 29% over 2 steps). 1H NMR (CDCl3) delta 7.56 (d, J=8.5Hz, 1H), 6.35 (d, J=8.5Hz, 1H), 5.00 (b s, 2H), 2.83 (t, J=8.8Hz, 2H), 1.66-1.79 (m, 2H), 1.43 (sxt, J=7.3Hz, 2H), 1.20-1.35 (m, 3H, impurity), 0.97 (t, J=7.3Hz, 3H), 0.90 (t, J=6.7Hz, 2H, impurity). 13C NMR (CDCl3) delta 166.3, 159.7, 141.1, 135.1 (impurity), 127.6 (impurity), 118.5, 105.5, 96.6, 36.7, 31.8 (impurity), 31.4, 29.0 (impurity), 22.6 (impurity), 22.4, 14.1 (impurity), 13.8.

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 53554-20-4, 6-Amino-2-chloronicotinonitrile.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915107-31-2 ,Some common heterocyclic compound, 915107-31-2, molecular formula is C8H8ClNO3, 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- (4- (Trifluoromethyl) phenyl) pyrrolidine (210 mg, 0.98 mmol) , methyl 6-chloro-5-methoxynicotinate (192 mg, 0.95 mmol) and K 2CO 3 (386 mg, 2.79 mmol) were dissolved in DMSO (6 mL) , and the mixture was heated to 100 and stirred for 5 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (60 mL) , and washed with water (15 mL) and saturated aqueous NaCl (15 mL×5) successively, dried over anhydrous Na 2SO 4 , and concentrated in vacuo to give a crude product, which was purified by silica-gel column chromatography (eluent: PET/EtOAc (v/v) = 5/1) to give a light yellow solid (280 mg, 75%) . [0690] MS (ESI, pos. ion) m/z = 381.2 [M+1] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,915107-31-2, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHONG, Xue; WANG, Feng; LI, Xuke; HE, Wei; PAN, Wei; HUANG, Jiuzhong; ZHANG, Yingjun; ZHENG, Changchun; (0 pag.)WO2020/11147; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54453-93-9, Adding some certain compound to certain chemical reactions, such as: 54453-93-9, name is Ethyl 2-Chloropyridine-4-carboxylate,molecular formula is C8H8ClNO2, 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 54453-93-9.

2.04 g of sodium borohydride are added portionwise to a solution of 1.7 g of ethyl 2-chloropyridine-4-carboxylate in 20 ml of ethanol, under an inert atmosphere of argon at a temperature in the region of 0 C. The reaction mixture is refluxed with stirring for 3 hours and then concentrated to dryness under reduced pressure. The residue thus obtained is taken up in dichloromethane and then washed with water. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. 1 g of 2-chloro-4-(hydroxymethyl)pyridine is thus obtained.

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. 54453-93-9, Ethyl 2-Chloropyridine-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2004/248884; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, 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: C5H3ClN2O3, blongs to pyridine-derivatives compound. COA of Formula: C5H3ClN2O3

(4c) 4-chloro-2-methoxy-5-nitropyridine 4-Chloro-5-nitropyridin-2-ol (1.18 g, 6.76 mmol) produced in Example 4 (4b) was suspended in tetrahydrofuran (15 mL) and, silver carbonate (2.80 g, 10.1 mmol) and methyl iodide (2.10 ml, 33.8 mmol) were added at room temperature, and the mixture was stirred at the same temperature for 13 hr. The insoluble material was filtered off with celite, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform). The solvent of the object fraction was evaporated under reduced pressure to give the title object compound as a pale-yellow powder (730 mg, yield 57%). 1H-NMR (CDCl3, 400 MHz) delta: 4.03 (3H, s), 6.90 (1H, s), 8.88 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Kyoto Pharmaceutical Industries, Ltd.; SHIRAHASE, Hiroaki; TAKAHASHI, Kenji; SHOJI, Yoshimichi; TAKEDA, Shigemitsu; (111 pag.)US2016/207883; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 490-11-9, 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. 490-11-9, name is Pyridine-3,4-dicarboxylicacid. A new synthetic method of this compound is introduced below.

Pyridine-3,4-dicarboxylic acid 42.1 (20 g, 121 mmol) was dissolved in methanol (400 ml)then concentrated sulfuric acid (12.9 ml, 242 mmol) was added and the mixture was stirredat reflux for 3 days. The volatiles were removed and the liquid poured carefully into saturatedsodium carbonate. The pH was adjusted to 7 with sodium carbonate then extracted threetimes with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered andevaporated to provide compound 42.2 (15.3 g, 65%) as an oil. 1H NMR (CDCI3, 300 MHz)O 3.95 (5, 6H), 7.50 (d, 1 H), 8.83 (d, 1 H), 9.06 (5, 1H). UPLC (CSH 2-50%) 0.60(196 [M+H]).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,490-11-9, Pyridine-3,4-dicarboxylicacid, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF SHEFFIELD; RICHARDS, Gareth; SKERRY, Timothy, M.; HARRITY, Joseph, P.A.; ZIRIMWABAGABO, Jean-Olivier; TOZER, Matthew, J.; GIBSON, Karl, Richard; PORTER, Roderick, Alan; BLANEY, Paul, Matthew; GLOSSOP, Paul, Alan; (369 pag.)WO2018/211275; (2018); 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. 25813-25-6, name is 3,5-Dibromopyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3,5-Dibromopyridin-4-ol

3,5-dibromopyridin-4-ol (239) (1.00 g, 3.95 mmols) was combined with phosphoryl chloride (921.45 mul, 9.89 mmols) in a pressure stable vessel. The vessel was closed and the solution heated to 140 C under stirring for 2.5 h. Afterwards the reation vessel was cooled down to rt and the reaction solution combined with ice cold water (75 mL). The aqueous layer was extracted with EtOAc (5 x 15 mL) and the combined organic layers were dried over anhydrous magnesium sulfate. The product was dried in vacuo. Purification of the crude was performed by silica gel column chromatography (1% EtOAc/n-pentane) to obtain the product (805 mg, 2.97 mmols, 75%) as a white solid. Rf: 0.32 (5% EtOAc/PE). 1H NMR (500 MHz, CDCl3) delta = 8.63 (s, 2H). 13C NMR (126 MHz, CDCl3) delta = 150.97, 144.13, 121.93. GC-MS: tR = 4.59 min; m/z = 268.8, 270.8, 272.8, 274.8 [M ]+. HRMS (ESI): calculated for C5H3N 79Br2 35Cl: m/z = 269.83153 [M+H]+, found: m/z = 269.83155 [M+H]+. calculated for C5H3N 79Br2 37Cl: m/z = 271.82858 [M+H]+, found: m/z = 271.82878 [M+H]+. calculated for C5H3N 79Br 81Br 37Cl: m/z = 273.82653 [M+H]+, found: m/z = 273.82597 [M+H]+. calculated for C5H3N 81Br2 35Cl: m/z = 275.82449 [M+H]+, found: m/z = 275.82316 [M+H]+.

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, 25813-25-6, 3,5-Dibromopyridin-4-ol.

Reference:
Article; Robke, Lucas; Rodrigues, Tiago; Schroeder, Peter; Foley, Daniel J.; Bernardes, Goncalo J.L.; Laraia, Luca; Waldmann, Herbert; Tetrahedron; vol. 74; 35; (2018); p. 4531 – 4537;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 144584-32-7, 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 144584-32-7 as follows.

Example 31 2-Chloro-3-bromo-4-(cis-4-tert-butylcyclohexylamino)pyridine 2.2 g (10 mmol) of 2,4-dichloro-3-bromopyridine, 1.86 g (12 mmol) of cis-4-tert-butylcyclohexylamine and 0.1 g ammonium chloride are warmed at 120 C. for 8 hours in 10 ml of N-methylpyrrolidone. After cooling, saturated aqueous sodium hydrogencarbonate solution is added and the reaction product extracted with ethyl acetate. Purification is carried out by column chromatography. Yield: 1.28 g (37%); RF: 0.41 (diisopropyl ether); 1 H-NMR (CDCl3) delta 7.92 (d, 1H), 6.38 (d, 1H), 5.27 (d, 1H), 3.74 (m, 1H), 1.0-2.0 (m, 9H), 0.89 (s, 9H) ppm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,144584-32-7, its application will become more common.

Reference:
Patent; Hoechst Schering AgrEvo GmbH; US5877322; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 685115-77-9, 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 685115-77-9, name is 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (100 mg, 0.36 mmol) and hydrogen peroxide. urea complex (72 mg, 0.77 mmol) in CH2Cb (2 ml.) cooled to 0 0C was added trifluoroacetic anhydride (0.10 ml_, 0.73 mmol). After 30 min the solution was warmed to r.t, after a further 16 hours a saturated solution of Na2S2Os (10 ml.) was added. The mixture was extracted with CH2CI2 (2 x 20 ml_), the combined organic extracts were washed with a saturated solution of NaHCOs (20 ml_), brine (20 ml_), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2CI2/Me0H, 98:2) to furnish the title compound as a white solid (20 mg, 19%), m.p. 130-133 0C; umax (CHCI3)/ cm”1 3026. 2855, 1724, 1452, 1273, 1 107.

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 685115-77-9, 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); 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. 905563-79-3, name is 2-Chloro-4-methoxynicotinaldehyde. A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-4-methoxynicotinaldehyde

(2) Synthesis of 2-chloro-4-methoxy-3-(2-methoxyvinyl)pyridine Under nitrogen atmosphere, 4.07g of (methoxymethyl) triphenylphosphonium chloride was suspended in 50ml of tetrahydrofuran, 1.37g of potassium tert-butoxide was added in an ice-cooling, which was stirred for 10 minutes. 1.02g of 2-chloro-4-methoxypyridine-3-carbaldehyde was dissolved in 20ml of tetrahydrofuran, which was added to reaction liquid, and was stirred for another 40 minutes. Water and diethyl ether were added to reaction liquid, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The reaction liquid was concentrated under a reduced pressure after removal of drying agent by filtration. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate) to give 1.18g of the title compound as a mixture of the geometric isomers.

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, 905563-79-3, 2-Chloro-4-methoxynicotinaldehyde.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1847535; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem