Month: April 2022

Reference of 1211523-71-5 , The common heterocyclic compound, 1211523-71-5, name is 2-(2-Bromopyridin-3-yl)acetonitrile, molecular formula is C7H5BrN2, 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: General procedure for indole synthesis by Cu-catalyzed amidation reaction. A dried re-sealable vialwith a Teflon stir bar was charged with amide (3.0 equiv, 1.5 mmol), CuI (5 mol%, 0.025 mmol), K3PO4(2.0 equiv, 1.0 mmol). The vial was sealed with a rubber septum and evacuated and refilled with argonthree times through a syringe needle. Under an argon atmosphere, toluene (0.5 mL),trans-1,2-diaminocyclohexane (20 mol%, 0.1 mmol) and aryl halide (0.50 mmol) were each added viasyringe. The rubber septum was then removed and quickly replaced with a Teflon screw cap and thereaction mixture was stirred at 110 C for 24 h. The resulting suspension was allowed to reach roomtemperature and filtered through a pad of silica gel eluting with AcOEt (10 mL). The filtrate wasconcentrated and the residue was purified by flash chromatography to afford a pure product.

The synthetic route of 1211523-71-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abe, Masahiro; Denneval, Charline; Nozawa-Kumada, Kanako; Kondo, Yoshinori; Heterocycles; vol. 92; 5; (2016); p. 900 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 443956-08-9 ,Some common heterocyclic compound, 443956-08-9, molecular formula is C5H3BrN2O3, 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.

Under an atmosphere of nitrogen, zinc powder (1.5 g,22.9 mmol) and NH4Cl (1.5 g, 22.9 mmol) were added to the solutionof 2-nitropyridin-3-ol (17) (1 g, 4.6 mmol) in C2H5OH (20 mL).The reaction was heated to 50 C and stirred for 16 h. The crudereaction mixture was filtered and purified by flash column chromatography(PE:EA 5:1) to provide the title compound 6-bromo-2-nitropyridin-3-ol (18) (524 mg, 60%). 1H NMR (400 MHz, DMSO)d 9.70 (s, 1H), 6.74 (d, J 7.8 Hz, 1H), 6.49 (d, J 7.8 Hz, 1H), 5.91 (s,1H); MS (M H): m/z 188.99.

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. 443956-08-9, 6-Bromo-2-nitropyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Shuxia; Fang, Yu; Wang, Huan; Gao, Hang; Jiang, Guohua; Liu, Jianping; Xue, Qianqian; Qi, Yueheng; Cao, Mengying; Qiang, Bingchao; Zhang, Huabei; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 255 – 266;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1214328-96-7, 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 1214328-96-7, name is Methyl 3-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

[01474] Step 2: Synthesis of methyl 3-bromo-4,6-dichloropyridine-2-carboxylate[01475] 0 a stjrre(j so]u ion of methyl 3-bromo-6-chloropyridine-2-carboxylate ( 1 .92 g, 7.67 mmol) in TFA ( 1 8ml) was added hydrogen peroxide (30% w/w aqueous solution, 5.22 ml, 53.7 mmol) and the reaction mixture was heated at 60C for 21 h. The reaction mixture was then cooled and slowly poured onto saturated 2C03 solution ( 100ml), followed by extraction of the aqueous layer with EtOAc (3x 100ml), washing of the combined organic phases with brine (2x50ml), drying (Na2S04) and evaporation. The desired 3-bromo-6-chloro-2- (methoxycarbonyl)pyridin- l -ium- l -olate (2.6 l g, -75% purity) was used crude in the next stage of the synthesis without any further purification. To the crude 3-bromo-6-chloro-2- (methoxycarbonyl)pyridin-l -ium- l – olate (-75% purity, 2.61 g, 7.35 mmol) was added POCl3 (3.42 ml, 36.7 mmol) and the solution was heated to 100C for 4h. After cooling the POCI3 was remove in vacuo to give a white solid which was columned over silica eluting with 0% to 10%) of EtOAc in heptane to afford the title compound as a pale yellow powder (1 .07 g, 49% over two steps). LC-MS 99%, 2.02 min (3.5 minute LC-MS method), m/z= 283.7/285.7/287.7, NMR (500 MHz, Chloroform-d) delta ppm 7.56 (s, 1 H) 4.00 (s, 3 H).

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 1214328-96-7, Methyl 3-bromo-6-chloropicolinate.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83766-88-5, 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 83766-88-5 as follows.

A 5-mL reactionvial was equipped with a stir bar, a rubber septum, and an argon inlet needle.The vial was charged with t-butoxypyridine(3) (1.2 mmol) and dry PhCH3(1 mL), and was allowed to stir at 0 C. MeOTf (1.2 mmol) was added dropwise tothe reaction mixture over 5 min. Upon complete addition, the reaction wasallowed to stir for 1h. The alcohol (1 mmol) dissolved in dry PhCH3or dry DCM (1 mL) depending upon the solubility of the alcohol, was added over30 seconds to the reaction mixture. The ice bath was removed and the reactionmixture was allowed to stir at room temperature (~ 23 C) for 1.5h. When thereaction was complete by TLC, the mixture was diluted in Et2O or DCMdepending upon the solubility of the product. Et2O was preferredbecause the hydroxypyridine/pyridone byproduct (5) was less soluble in this solvent than DCM. The diluted reactionmixture was washed with water (10 mL), then brine (10 mL). The organic fractionwas dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to isolate the crude productmixture. The crude mixture was purified by flash chromatography to yield thepure t-butyl ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; Salvati, Anna E.; Hubley, Christian T.; Albiniak, Philip A.; Tetrahedron Letters; vol. 55; 51; (2014); p. 7133 – 7135;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 52605-96-6, 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 52605-96-6, name is 2-Chloro-3-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the product of step 1 (12.8 g, 89.16 minol) in TFIF (100 mL) at .-70 was added LDA (67 rnL) dropwise. After stirring for 40 mm, a solution of 12 (29.5 g, 116rnmol) in THF (50 rnL) was added dropwise. The mixture was stirred at -70 C for 5 h, sat, aq. NHCl added and the mixture extracted with EtOAc (100 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica (10% EtOAc in petroleum ether) to give the title compound as a solid. LRMS miz (M+H) 269.1 found, 269.1 required.

According to the analysis of related databases, 52605-96-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72587-18-9, 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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

Production Example 14 (1) [0776] A mixture of 5.14 g of 3-amino-2-chloro-5-trifluoromethylpyridine, 3.92 g of zinc cyanide, 1.19 g of tris(dibenzylideneacetone)dipalladium(O), 1. 45 g of 1,1′-bis (diphenylphosphino) ferrocene and 20 ml of DMF was stirred at 150C for 40 minutes. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, then combined with the organic layer of the filtrate and washed with water, and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and then the resulting residue was applied to a silica gel column chromatography to obtain 2.23 g of 3-amino-2-cyano-5-trifluoromethylpyridine. 3-Amino-2-cyano-5-trifluoromethylpyridine 1H-NMR(CDCl3)delta: 8.29(1H, d), 7.33(1H, d), 4.70(2H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; TAKAHASHI, Masaki; ITO, Mai; NOKURA, Yoshihiko; TANABE, Takamasa; SHIMIZU, Chie; EP2865671; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1197294-80-6, 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 1197294-80-6, name is tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate (1.00 g, 2.66 mmol), 5-chloro-2-hydroxyphenylboronic acid (458 mg, 2.66 mmol) and sodium carbonate (1.13 g, 10.64 mmol) were combined and dissolved in a mixture of dioxane/water (14 mL/4 mL). The reaction mixture was degassed for 20 min with nitrogen and then tetrakistriphenylphosphinepalladium (0) (153 mg, 0.133 mmol) was added. The reaction mixture was heated at 70 C. for 18 hours and then partitioned between ethyl acetate (20 mL) and water (10 mL). The organic layer was separated, washed with brine (10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage (10% to 60% ethyl acetate in heptane over 20 CV) to give the title compound (700 mg, 66%) as a white solid.1H NMR (400 MHz, CD3OD): delta 1.40 (s, 9H), 3.50 (s, 8H), 6.80-6.90 (m, 2H), 6.95 (s, 1H), 7.15 (d, 1H), 7.30 (s, 1H), 8.05 (d, 1H).LCMS Rt=2.48 minutes MS m/z 388 [M-H]-.

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 1197294-80-6, tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; ICAGEN INC.; PFIZER LIMITED; US2012/10182; (2012); 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. 623585-74-0, name is Methyl 2,5-dichloroisonicotinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 2,5-dichloroisonicotinate

To a cold solution of methyl 2,5-dichloroisonicotinate (500 mg, 2.42 mmol) in THF (15 mL) was added N-Methyl-2-pyrrolidone (1.4 mL), iron(III)acetyl acetone (43 mg, 0.12 mmol) and methyl magnesium bromide (36 mg, 0.305 mmol) at 0C. The reaction mixture was stirred at 0C for 1 h and then at rt for 18 h. The reaction mixture was quenched with brine and was extracted with ethyl acetate. The organic layer was separated, dried, filtered and concentrated to afford 130 mg of the title product.1H NMR (300 MHz, DMSO d6): delta 8.46 (s, 1H), 7.74 (s,lH), 3.87 (s, 3H), 2.44 (s, 3H).

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, 623585-74-0, Methyl 2,5-dichloroisonicotinate.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/72825; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116986-09-5 ,Some common heterocyclic compound, 116986-09-5, molecular formula is C8H8BrNO2, 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.

A mixture of 2-hydroxyl-5-methoxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (1.2eq) was added to this mixture and the reaction was stirred at room temperature for 8-10 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 3:2 to obtain pure product as pale yellow powder with a yield of 82%. IR (Diamond, cm-1): 2897, 1712, 1671, 1607, 1567, 1490, 1445, 1398, 1365, 1275, 1232, 1 165, 1 139, 1 106; 1H-NMR (400 MHz, DMSO-d6): d 10.35 (s, 1H), 8.65 (dd, J = 4.6, 1.28 Hz, 1H), 8.2 (dd, J = 7.84, 0.76 Hz, 1H), 7.66 (dd, J= 7.88, 4.68 Hz, 1H), 7.24 (m, 3H), 5.49 (s, 2H), 3.83 (s, 3H), 3.77(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 188.81, 166.12, 154.66, 153.55, 148.49, 146.69, 136.89, 133.04, 126.43, 124.89, 122.96, 1 15.79, 1 10.68, 67.44, 55.56, 52.34. MS (ESI) m/z found 324.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 98% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); A1;,
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. 25813-25-6, name is 3,5-Dibromopyridin-4-ol, the common compound, a new synthetic route is introduced below. Application In Synthesis of 3,5-Dibromopyridin-4-ol

Compound (M-41) (10.0 g, 39.5 mmol) was suspended in acetonitrile (50 mL), DIPEA (15 mL, 87 mmol) wasadded at room temperature, phosphoryl chloride (7.4 mL, 79 mmol) was added under ice-cooling, and the mixture wasstirred with heating under reflux for 17 hr. The mixture was allowed to cool, and the reaction mixture was added dropwiseto ice water, and neutralized with sodium carbonate (11.6 g, 138 mmol). Thereafter, the mixture was extracted with ethylacetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solventwas evaporated under reduced pressure to give a chloro compound (yield 10.6 g, 99%) as a brown solid. The chlorocompound (10.6 g, 39.1 mmol) was dissolved in THF (70 mL), sodium methoxide (28% methanol solution, 14 mL, 59mmol) was added, and the mixture was stirred at 60C for 30 min. The mixture was allowed to cool, water was addedto the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successivelywith water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reducedpressure to give compound (VII-46) (yield 9.21 g, 88%) as a yellow solid

The synthetic route of 25813-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem