Tag: M.W:200-300

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. 153034-90-3, name is 2-Chloro-4-iodonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloro-4-iodonicotinaldehyde

Step 1. 2-chloro-4-iodonicotinonitrileTo 2-chloro-4-iodonicotinaldehyde (1.0 g, 3.7 mmol) dissolved in THF (11 mL) was added ammonium hydroxide (11 mL, 280 mmol) followed by iodine (1040 mg, 4.11 mmol), the reaction was held at ambient temperature 3.5 h, color visibly lightens as reaction progresses until the end when it is nearly colorless. LCMS indicates reaction to be complete. Reaction was quenched by addition of saturated NaHSO3, extracted into EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the crude product, 926 mg. Dissolved in CHCl3/MeOH and applied to 120 g silica gel column, the product fractions were concentrated in vacuo to give 728 mg product. The purified material was taken directly to next step.

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, 153034-90-3, 2-Chloro-4-iodonicotinaldehyde.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 83004-10-8, 2-Bromo-6-(bromomethyl)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, Formula: C6H5Br2N, blongs to pyridine-derivatives compound. Formula: C6H5Br2N

To a stirred solution of N-hydroxy-1-(4-methyl-4H-1 ,2,4-triazol-3-yl)-1- phenylmethanimine (0.45 g, 2.22 mmol, 1.0 eq.) in 20 ml of MeCN was added C82CO3 (0.795 g, 2.44 mmol, 1.1 eq.) followed by Kl (0.0365 g, 0.22 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2-bromo-6-(bromomethyl)pyridine (0.586 g, 2.33 mmol, 1.05 eq.) in one portion. The reaction was stirred for 4 h at room temperature. The solid was removed by filtration and washed with 250 ml of fresh MeCN. The filtrate was evaporated, and 500 ml of EtOAc were added. The organic layer was washed with H2O and dried over MgSO4 then concentrated. Chromatography of the crude on silica gel gave N-[(6- bromopyridin-2-yl)methoxy]-1-(4-methyl-4H-1 ,2,4-triazol-3-yl)-1-phenylmethanimine (0.748 g, 90 % yield) as a yellow oil. HPLC/MS : m/z = 373 (M+H)

The synthetic route of 83004-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE SA; WO2009/130193; (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 70158-59-7, name is 2,5-Dichloro-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2,5-Dichloro-3-(trifluoromethyl)pyridine

Step 9 Methyl 4-{[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy}-5,8-dimethyl-1,1-dioxo-1,2,3,4-tetrahydro-1lambda6-thiochromene-6-carboxylate 0.48 g (1.7 mmol) of methyl 5,8-dimethyl-4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-1lambda6-thiochromene-6-carboxylate and 0.4 g (1.9 mmol) of 2,5-dichloro-3-(trifluoromethyl)pyridine were dissolved in 20 ml of tetrahydrofuran and subsequently admixed with 0.21 g (1.9 mmol) of potassium tert-butoxide. The mixture was stirred for 3 h and subsequently concentrated using a rotary evaporator. The residue was taken up in 100 ml of ethyl acetate, washed with sat. NaCl solution (2*20 ml), dried over MgSO4 and concentrated using a rotary evaporator. The residue was purified by chromatography (silica gel, ethyl acetate: heptane=1:3). Yield: 0.64 g (80% of theory); yellow crystals; Rt=0.71 (silica gel/ethyl acetate); 1H NMR (CDCl3): delta 2.35 (s, 3H), 2.8 (m, 2H), 2.8 (s, 3H), 3.25 (s, 1H), 3.8 (m, 1H), 3.9 (s, 3H), 6.6 (m, 1H), 7.7 (s, 1H), 7.95 (m, 1H), 8.4 (m, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 70158-59-7.

Reference:
Patent; Hoechst Schering AgrEvo GmbH; US6297196; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 79491-45-5, 2,6-Dibromo-3-methoxypyridine, 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, 79491-45-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To conc H2SO4 (15 ml) at 0 C were added nitric acid (67%, 4.0 mL) and KNO3 (2.0 g) followed by Compound 137 (2.0 g, 7.5 mmol). The reaction mixture was stirred at 65 C overnight, after which it was poured into crushed ice and neutralized carefully with solid Na2C03, then extracted with EtOAc (2 times). The combined organic extracts were concentrated, and the resulting residue was purified by flash silica gel chromatography (0-80% of EtOAc in hexanes) to give Compound 138 (732 mg, 31% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,79491-45-5, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59237-53-5, 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 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A flask was charged with methyl-6-chloro-5-nitronicotinate (2.00 g, 9.23 mmol), PdC12(PPh3)2 (324.00 mg, 461.70 jimol) and Cul (87.90 mg, 461.70 jimol). The system was evacuated and filled thrice with N2 before addition of TEA (44 mL) and DMF (88 mL) and the resulting solution was degassed with N2 for 10 mm. Thencyclopropylacetylene (1 .56 mL, 18.49 mmol) was added and the reaction mixture was stirred at rt for 18 h. Then, the reaction mixture was concentrated. The residue was purified by column chromatography on silica gel (Irregular SiOH 15-40 jim, 80 g, dry loading on celite®, mobile phase: heptane/DCM, gradient from 50:50 to 0:100). The fractions containing the product were combined and concentrated under vacuum to give1.3 g of intermediate 293 (58percent yield, brown solid).

According to the analysis of related databases, 59237-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15862-37-0, 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 15862-37-0, name is 2,5-Dibromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 5-Bromo-2-(4-chloro-3,5-difluorophenyl)-3-nitropyridine A 24/40-100 mL round bottom flask was charged with 2,5-dibromo-3-nitropyridine (2.00 g, 7.09 mmol) and 2-(4-chloro-3 ,5 -difluorophenyl)-4,4,5 ,5 -tetramethyl-1,3,2-dioxaborolane (1.95 g, 7.09 mmol). The mixture was diluted with THF(30 mL), and PdC12(dppf) (0.0520 g, 0.07 10 mmol) was added followed by aq. potassiumphosphate tribasic, (2.0 M, 7.09 mL, 14.2 mmol). The vial was sealed and degassed usingultra pure argon and sonication for 2 mm. The vial was placed in an oil bath preheated to65 C. After 35 mm, the reaction mixture was concentrated under reduced pressure,diluted with ethyl acetate and a brine solution, and filtered through a pad of Celite. The contents of the flask were transferred into a separatory funnel, and the organic was washed with brine (3X) and then back extracted with ethyl acetate. The combined organics were dried with magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (40 g ISCO RediSep Rf, loaded inlwith:DCM and dried, initial waste: 0 mL, fraction size: 9 mL 13x 100 mm, and eluted with dichloromethane in hexanes 0% [102 mL], 0-20% [150 mL], 20% [501 mL], 20-50% [252 mL], 50% [150 mL]). The fractions were collected to give 1.59 g (64%). ?H NMR (400MHz, CDC13) oe 8.94 (d, J=2.0 Hz, 1H), 8.37 (d, J=2.3 Hz, 1H), 7.23-7.16 (m, 2H). Mass found 350 [M+H].

According to the analysis of related databases, 15862-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58596-88-6 ,Some common heterocyclic compound, 58596-88-6, molecular formula is C6H4Cl2N2O2, 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.

(2e) 6-Chloro-5-methyl-3-nitro-2-pyridinamine [Formula 22]; A mixture of 2,6-dichloro-3-methyl-5- nitropyridine (10.41 g, 50.3 mmol), 28% aqueous ammonia solution (17 ml, 0.25 mol), potassium carbonate (10.4 g, 75.5 mmol) and t-butanol (167 ml) was stirred overnight at 60C under nitrogen atmosphere. After stirring at room temperature for 3 hours, a precipitate was filtered and then washed three times with water, thereby yielding the title compound (4.25 g, 22.7 mmol, 45%) as a yellow solid. ¹H NMR(400MHz, QMSO-D6) No. ppm; 2.23,(3H, s), 8.04(2H, br s), 8.39(1H, s).

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. 58596-88-6, 2,6-Dichloro-3-methyl-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 164513-39-7, 5-Bromo-2-methoxy-4-methylpyridine, 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: 164513-39-7, blongs to pyridine-derivatives compound. SDS of cas: 164513-39-7

Intermediate 31 (50% purity, 165 mg, 0.25 mmol), 5-bromo-2-methoxy-4-methyl-pyridine (75 mg, 0.37 mmol) and 2M aqueous potassium carbonate solution (0.43 mL)were combined in 1 ,4-dioxane (5 mL). Bis[3-(diphenylphosphanyl)cyclopenta-2,4-dien- 1 -yl]iron-dichloropalladium-dichloromethane complex (10 mg, 0.01 mmol) was added, and the mixture was heated at 90C for 18 h. The mixture was partitioned between ethyl acetate (20 mL) and water (15 mL). The organic layer was dried over sodium sulfate andconcentrated under vacuum. The residue was purified by flash chromatography, eluting with 0-100% ethyl acetate in heptanes followed by 0-20% methanol in DCM. The crude product was then further purified by preparative HPLC (Method C) to afford the title compound (23 mg, 23%) as a white solid. OH NMR (500 MHz, CDC13) 7.89 (s, 1H), 7.62(d, J9.2 Hz, 1H), 7.59 (s, 1H), 7.24 (d, J7.3 Hz, 1H), 7.13 (d, J8.1 Hz, 1H), 7.10 (dd, J9.2, 1.3 Hz, 1H), 7.06 (t, J7.5 Hz, 1H), 6.83 (d, J7.4 Hz, 1H), 6.55 (m, 2H), 4.28 (s, 2H),3.93 (s, 3H), 2.52 (s, 3H), 2.11 (s, 3H). Method A HPLC-MS: MH+ m/z 410, RT 3.20 minutes (99%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,164513-39-7, 5-Bromo-2-methoxy-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA S.A.; BENTLEY, Jonathan Mark; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; CAIN, Thomas Paul; CHOVATIA, Praful Tulshi; FOLEY, Anne Marie; GALLIMORE, Ellen Olivia; GLEAVE, Laura Jane; HEIFETZ, Alexander; HORSLEY, Helen Tracey; HUTCHINGS, Martin Clive; JACKSON, Victoria Elizabeth; JOHNSON, James Andrew; JOHNSTONE, Craig; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LEIGH, Deborah; LOWE, Martin Alexander; MADDEN, James; PORTER, John Robert; QUINCEY, Joanna Rachel; REED, Laura Claire; REUBERSON, James Thomas; RICHARDSON, Anthony John; RICHARDSON, Sarah Emily; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2014/9295; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69045-79-0, 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. 69045-79-0, name is 2-Chloro-5-iodopyridine. A new synthetic method of this compound is introduced below.

Zinc dust (127mg, 1.94mmol, 1.1eq) was dried for 18h at 100C in vacuo, transferred to a round bottomed flask and heated with a hot air gun under vacuum. The flask was allowed to cool to room temperature and DMF (2ml) and 1,2-dibromoethane (12mul, 0.141mmol, 0.08eq) added. The mixture was heated to 70C for 10 mins, allowed to cool to r. t., and TMSCI (18mul, 0.141mmol, 0.08eq) added dropwise. This mixture was stirred at r. t. for 30min before dropwise addition of 3-iodoazetidine-1-carboxylic acid tert-butyl ester (Ref SynLett, 1998,4, 379)(500mg, 1.766mmol, 1.Oeq) as a solution in DMF (2ml). The mixture was stirred at 40C for 1 h. 2-chloro-5-iodopyridine was dissolved in DMF (2ml) and added, followed by Pd2dba3 (32mg, 0.035mmol, 0.02eq) and tri-2-furylphosphine (17mg, 0.071mmol, 0.04eq) and the mixture heated to 70C for 4h. The mixture was allowed to cool, diluted with Et20(40ml) and NH4CI (40ml, sat’d aq), layers separated, the aqueous layer was re-extracted with Et20(20ml), organics combined, washed with brine (2x30ml), dried (MgS04), filtered and evaporated to give a yellow solid. This solid was flash chromatographed on silica gel with a gradient elution from 100% CH2CI2 to 99: 1 CH2CI2:MeOH to give 235mg of impure product. This material was further purified by fish chromatography on silica get with a gradient elution from 100% toluene to 95:5 toluene:EtOAc to give the title compound as a yellow solid (193mg, 41%) Tlc Rf = 0.13 (10%EtoAc/Toluene UV visualisation) MS (APCI+) 269 (MH+) ¹H NMR: No.H (400 MHz, CDCI3) 8.3 (1 H, s), 7.7 (1 H, m), 7.35 (1 H, d), 4.35 (2H, t), 3.9 (2H, t), 3.65-3.8 (1 H, m), 1.45 (9H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69045-79-0, 2-Chloro-5-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/115985; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-40-5 ,Some common heterocyclic compound, 17282-40-5, molecular formula is C9H12BrNO2, 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.

General procedure: Chromenone 1a (0.5 mmol), pyridinium salts 2a (0.55 mmol), DBU (1.0 mmol) and 1,4-dioxane (3.0 mL) were dissolved in 10 mL round-bottomed flask and stirring at 80 C for 12 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled down to room temperature and concentrated in vacuum to give the crude product, which was further purified by silica gel chromatography (ethyl acetate: petroleum =1:5) to afford the desired product. 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-40-5, its application will become more common.

Reference:
Article; Dong, Kai-Kai; Huang, Qiang; Tetrahedron Letters; vol. 60; 29; (2019); p. 1871 – 1874;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem