Category: pyridine-derivatives

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. 76093-33-9, name is (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. name: (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

EXAMPLE 11 Production of 3-(1-methyl-2-pyridinium)methyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-3-carboxylate iodide STR21 To a solution of 1 g (3.01 mmol) of (4R)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-3-carboxylic acid in 4 ml of THF were added 1.23 g (7.50 mmol) of 2-(chloromethyl)pyridine and 460 mg (3.35 mmol) of potassium carbonate and the mixture was stirred at room temperature for 5 hours. The mixture was diluted with 50 ml of ethyl acetate, washed with water, and hydrated and dried over salt cake. Thereafter, the solvent was distilled off under reduced pressure to obtain 1.13 g of the residue. The residue was passed through a silica gel column for purification to obtain 673 mg of 3-(2-pyridyl)methyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-3-carboxylate.

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, 76093-33-9, (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid.

Reference:
Patent; Mercian Corporation; US6133443; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211533-83-3, 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. 1211533-83-3, name is 5-Bromo-6-methoxypyridin-2-amine, molecular formula is C6H7BrN2O, 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 solution of 5-bromo-6-methoxypyridin-2-amine (1.0 g, 4.9 mmol) in DCM (20.0 mL) was added 2-methylbenzenesulfonyl chloride (1.1 g, 5.9 mmol, 853.6 uL) and pyridine (1.2 g, 14.8 mmol, 1.2 mL). The mixture was stirred at 45C for 12 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (S1O2, Petroleum ether / Ethyl acetate = 100/1 to 50/1) to afford N-(5-bromo-6-methoxypyridin- 2-yl)-2-methylbenzenesulfonamide (1.0 g, 2.5 mmol, 52.2% yield). M+H+ = 357.0 (LCMS).

According to the analysis of related databases, 1211533-83-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (214 pag.)WO2019/94641; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65753-47-1, Adding some certain compound to certain chemical reactions, such as: 65753-47-1, name is 2-Chloro-3-(trifluoromethyl)pyridine,molecular formula is C6H3ClF3N, 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 65753-47-1.

2-Chloro-3-trifluoromethyl-pyridine (3 g, 16.53 mmol) was dissolved in 30ml of a solution of sodium methoxide (5.4M) in methanol. The mixture was stirred at ambient temperature for 2 days. After this period of time, the reaction was taken into ice and extracted with DCM three times. The combined extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 2-methoxy-3-trifluoromethyl-pyridine as a light liquid (2.7 g, 89% yield). 1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 3.98 (s, 3H) 7.2 (dd, 1 H) 8.1 1 (d, 1 1-1) 8.45 (d, 1 H). MS: 178.1 [M+1 ]+, Rt(1) =1 .29 min.

According to the analysis of related databases, 65753-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, molecular formula is C12H11ClN2O, 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.

Following hydrogenation to form the first aniline intermediate, acid catalyzed coupling was performed to prepare 4-[3-chloro-4-(2-pyridylmethoxy)anilino]-3-cyano-7-ethoxy-6-N-acetylaminoquinoline, as shown below: To perform the coupling reaction, the two reactants were heated together in alcohol at 65-78 C. over 4-6 hours, yielding the product. The reaction begins as an amber slurry and thickens to a lighter beige slurry as it approaches completion. Upon scaling up from 75 g to 350 g, it proved necessary to add a catalytic amount (0.025 eq.) of methanesulfonic acid to initiate the reaction. As a specific example, 4-chloro-3-cyano-7-ethoxy-6-N-acetylaminoquinoline (0.141 kg, 0.49 mole) was added to the mixture of Example 2, followed by ethanol (0.037 L) to give a suspension. A catalytic amount of methanesulfonic acid (1.17 g) was added at 20-25 C. The resulting slurry was heated to 70-75 C. and held for a minimum of 4 hours. Thickening of the slurry was evident after 1.5 hours. Following reaction completion, the mixture was cooled to room temperature and may be used ?as is? in the telescoped reaction of Example 4 below.; As solvents EtOH, DMF or other suitable solvent may be used. Experimental results obtained using different solvents and reaction conditions are shown in Table 3. Difficulty filtering the product of this step (noted in several entries on Table 3) was circumvented by not isolating the solid at this point, but telescoping the reaction with the next step. It has been found that on the order of 20 volumes of EtOH were necessary to achieve reasonable stirring, but that the reaction can proceed in only 10 volumes of DMF, without significant loss in purity. In Table 3, where the entry is labelled NI, the intermediate product was not isolated, but carried into the next reaction step. TABLE 3 Coupling Reaction Coupling Temp Time Yield Solvent Solvent ( C.) (h) (%) Comments IPA EtOH 78 4 85.4 contains impurity THF EtOH 78 4 90.5 v. slow filtration THF THF 68 4 NA Only 16% product formed THF EtOH 78 4 94.2 v. slow filtration EtOH IPA 82 5 NA No reaction EtOH MeOH 65 5 60.0 v. slow filtration THF EtOH 78 1.5 80.3 v. slow filtration (MeSO3H) THF EtOH 78 4 86.0 v. slow filtration THF EtOH 78 3 85.7 4 h filtration – hard, green (MeSO3H) coated solid on drying THF Dimethoxy 85 2 74.2 Faster filtration (<1 hr) ethane Nice yellow solid THF Diethoxy 85 5 - - Methane THF Dimethoxy 70 6 - - Ethane THF EtOH 78 6 96.6 Slow filtration THF DMF 78 0.5 65.6 Some product lost in filtrate (MeSO3H) THF DMF 70 8 NI See Note 1 (MeSO3H) THF EtOH 78 6 ND See Note 2 (MeSO3H) THF EtOH 78 4 NI Yield to the free base is (MeSO3H) 80.4%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 83%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 86%3/ NR = no reaction, NI = not isolated; ND = not determined; NA = not available 1. Carried through to the deprotection and generation of free base to give 69.5% overall yield. 2. The overall yield after the deprotection and generation of the free base is 76.1% 3This reaction was not filtered at all but taken as slurry to the next step. 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 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 97483-77-7 ,Some common heterocyclic compound, 97483-77-7, molecular formula is C6H3BrN2, 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.

Pyridine (40.0 mL, 4.0 v/w) was placed in a reactor, and zinc chloride (11.2 g, 81.9 mmol) was added dropwise at 40C or less. Thereafter, sodium azide (8.90 g, 137 mmol) and 5-bromo-2-cyanopyridine (10.0 g, 54.6 mmol) were added into the reactor, and the reaction mixture was stirred to reflux at 120C for 2 hr. After the termination of the reaction, the reaction product was cooled to room temperature, added with purified water (200 mL, 20.0 v/w), stirred at room temperature for 1 hr, filtered, and washed with purified water (200 mL, 20.0 v/w). The filtered solid was added with a 6 N hydrochloric acid aqueous solution (200 mL, 20.0 v/w) and then stirred at room tem[43jperature for 2 hr. The reaction product was filtered, washed with purified water (200mL, 20.0 v/w), and concentrated under reduced pressure, thus yielding a desired whitecompound. Yield (11.34 g, 91.8%), Purity 99.4%5-bromo-2-(2H-tetrazol-5-yl)pyridine:1H NMRoe (DMSO-d6, ppm) 8.95 (d,1H), 8.35 (dd,1H), 8.17 (d,1H)

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. 97483-77-7, 5-Bromopicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ST PHARM CO., LTD.; WOO, Seok Hun; CHOI, YunHee; KIM, Hong Jun; CHANG, Sun Ki; LIM, Geun Jho; (14 pag.)WO2017/99530; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1796-83-4, 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 1796-83-4, name is Dimethyl pyridine-3,4-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step A. Dimethyl pyridine-3,4-dicarboxylate 1 -oxideTo a stirred mixture of dimethyl pyridine-3,4-dicarboxylate (10.13 g, 51.9 mmol) and urea hydrogen peroxide (9.80 g, 104 mmol) in CH3CN (100 mL) at 0 0C was added dropwise trifluoroacetic anhydride (22.31 g, 106 mmol). The reaction mixture was stirred at 0 10 0C for 2 h, and then saturated aqueous sodium bisulfite (80 mL) was added slowly and the quenched mixture was diluted with 0.5 N HCl (300 mL) and extracted with CH2Cl2 (3 x 400 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: mlz = 212 (M + 1).

According to the analysis of related databases, 1796-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/120652; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54664-55-0, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]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, HPLC of Formula: C8H8ClN, blongs to pyridine-derivatives compound. HPLC of Formula: C8H8ClN

Step 3 : 4-chloro-6,7-dihydro-5H-cvclopentarb1pyridine-l-oxide To a solution of 4-chloro-6,7- dihydro-5H-cyclopenta[b]pyridine (38 g, 247 mmol) and methyl trioxorhenium(VII) (400 mg, 1.61 mmol) in DCM (250 mL) was added hydrogen peroxide (76 mL, 742 mmol, 30%wt). After addition, the mixture was stirred at 20C for 48h. TLC showed SM was consumed. The mixture was diluted with DCM (300 mL) and water (150 mL), quenched with solid powder sodium sulfite portionwise until potassium iodide-starch test paper (the paper wetted by lmol/L aqueous HC1) did not turn blue. The organic phase was separated and the aqueous phase was extracted with CHCI3 (500 mL chi 3). The combined organic phases were dried over Na2S04, filtered and concentrated to give the title compound, which was used for the next step without further purification.

The synthetic route of 54664-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERTZ, Eric; EDMONDSON, Scott, D.; SO, Sung-Sau; SUN, Wanying; LIU, Weiguo; NEELAMKAVIL, Santhosh, F.; GAO, Ying-Duo; HRUZA, Alan; ZANG, Yi; ALI, Amjad; MAL, Rudrajit; HE, Jiafang; KUANG, Rongze; WU, Heping; OGAWA, Anthony, K.; NOLTING, Andrew, F.; (152 pag.)WO2016/168098; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 90902-83-3, Adding some certain compound to certain chemical reactions, such as: 90902-83-3, name is 3-Amino-2-bromo-5-chloropyridine,molecular formula is C5H4BrClN2, 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 90902-83-3.

Example 45: N-(2-Bromo-5-chloro-pyridin-3-yl)-4-tenVbutyl-N-methoxymethyl- benzenesulfonamide; [00436] A 200 mL round-bottom flask was charged with 2-bromo-5-chloro- pyridin-3-ylamine (10.4 g, 50.0 mmol), 4-tert-butyl-benzenesulfonyl chloride (20.0 g, 85.0 mmol), and pyridine (38 mL). The resultant solution was heated to 70 C and stirred overnight. The following day, the pyridine was removed by removed in vacuo and THF (30 mL) and 4.0 N NaOH (100 mL) were added and the reaction was stirred at 60 C overnight. The organics were subsequently removed in vacuo and the residues were diluted with water (400 mL). The small quantity of insoluble solid was removed by filtration and the pH was adjusted to 6-7 with concentrated HCI. The resultant aqueous solution was extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated under reduced pressure to afford the diarylsulfonamide (13.4 g) in 66 % yield. To a solution of the crude sulfonamide (12.0 g, 35.0 mmol) and K2CO3 (24.0 g, 170 mmol) in anhydrous THF (80 mL) was added chloromethyl methyl ether (4.0 mL, 52.7 mmol). The resultant heterogeneous solution was stirred for 60 min at ambient temperature and the solids were subsequently removed via filtration. The filtrate was then removed in vacuo and the residue was dissolved in EtOAc. The organics were washed with saturated Na2CO3, dried over MgSO4, and evaporated in vacuo to generate a brownish oil. The oil was triturated with hexanes and the resultant solid filtered to produce the desired product as a light yellowish solid (11.5 g, 86% yield).

According to the analysis of related databases, 90902-83-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
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. 82257-09-8, name is 3-Bromo-4-methoxypyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 82257-09-8

To a stirred solution of tert-butyl 4-[(2-{[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 Hbenzimidazol-2-yl]amino}pyridin-4-yl)methyl]piperazine-1 -carboxylate (400 mg, 748 pmol) and 3-bromo-4-methoxypyridine (169 mg, 898 pmol) in dioxane (4 mL) and water (0.7 mL) wasadded sodium carbonate (238 mg, 2.25 mmol) and Pd(dppf)Cl2. CH2CI2 (91.7 mg, 112 pmol). The mixture was heated to reflux for 24 h. Further 3-bromo-4-methoxypyridine (70 mg) was added and the mixture was heated to reflux for 24 h. Dichioromethane was added, the mixture was dried (magnesium sulfate), filtered and the solvent was removed in vacuum. Silicagel chromatography gave 16.0 mg (4% yield) of the title compound as a crude product that wasused without further purification.LC-MS (Method 2): R = 1.20 mm; MS (ESIpos): m/z = 516 [M+H]1H-NMR (400 MHz, CHLOROFORM-d) oe [ppm]: 1.261 (0.74), 1.468 (16.00), 2.330 (1.89),3.394 (1.99), 3.444 (1.92), 3.927 (1.16), 6.927 (0.58), 6.941 (0.64), 6.953 (0.79), 6.965 (0.70),7.081 (1.09), 8.283 (0.78), 8.296 (0.74), 8.483 (0.57), 8.497 (0.56), 8.540 (1.04).

The synthetic route of 82257-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1187236-18-5, Adding some certain compound to certain chemical reactions, such as: 1187236-18-5, name is Ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate,molecular formula is C10H9BrN2O2, 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 1187236-18-5.

A mixture of 258-2 (300 mg, 1.12 mmol), B (356 mg, 1.23 mmol), Cul (21 mg, 0.11 mmol), K3PO4 (473 mg, 2.23 mmol), and picolinic acid (28 mg, 0.22 mmol) in DMSO (6 ml) is sparged with N2 for 5 min, and heated at 90 C overnight. The reaction mixture is cooled to ambient temperature, diluted with EtOAc and water, and filtered. The filtrate is washed with water and brine. The organic layer is dried, concentrated, and purified Si02 (0-6%, MeOH in DCM) to give 258-3

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. 1187236-18-5, Ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ABEYWARDANE, Asitha; BRUNETTE, Steven Richard; BURKE, Michael Jason; KIRRANE, Thomas Martin, Jr.; MAN, Chuk Chui; MARSHALL, Daniel Richard; PADYANA, Anil Kumar; RAZAVI, Hossein; SIBLEY, Robert; SMITH KEENAN, Lana Louise; SNOW, Roger John; SORCEK, Ronald John; TAKAHASHI, Hidenori; TAYLOR, Steven John; TURNER, Michael Robert; YOUNG, Erick Richard Roush; ZHANG, Qiang; ZHANG, Yunlong; ZINDELL, Renee M.; WO2014/14874; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem