Month: April 2022

Synthetic Route of 2604-39-9, 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. 2604-39-9, name is 2-Chloro-5-nitropyridin-4-amine. A new synthetic method of this compound is introduced below.

To a solution of 2-chloro-5-nitropyridin-4-amine (5.0 g, 28.8 mmol, 1.0 eq.) in DMF (20 mL) was added NBS (6.16 g, 34.6 mmol, l.2 eq.) in several portions. After stirring at room temperature for 4 hrs, most of the solvent was removed under reduced pressure, the residue was suspended in cool water (30 mL), and the solid was filtered and dried under reduced pressure to give 3- bromo-2-chloro-5-nitropyridin-4-amine (6.2 g, 85% yield) as an off-white solid. LC-MS (ESI): m/z 252, 254 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2604-39-9, 2-Chloro-5-nitropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; LI, Mingzong; LIU, Peng; MEDEIROS, Matthew; REZNIK, Samuel K.; SUI, Zhihua; TRAVINS, Jeremy M.; POPOVICI-MULLER, Janeta; ZHOU, Shubao; MA, Guangning; (298 pag.)WO2019/191470; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-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, Quality Control of 2-Bromo-5-hydroxy-3-methylpyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-5-hydroxy-3-methylpyridine

(A) A mixture of 552 6-bromo-5-methylpyridin-3-ol (1 g, 5.32 mmol), 188 1-bromo-2-methoxyethane (730 mg, 5.25 mmol) and 149 K2CO3 (1.5 g, 10.87 mmol) in 16 MeCN (20 mL) was stirred at rt overnight, after which the reaction was quenched by the addition of 12 water (100 mL). The resulting solution was extracted with EtOAc (2×100 mL) and the combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by silica gel chromatography (0-15% EtOAc/petroleum ether) to afford 553 2-bromo-5-(2-methoxyethoxy)-3-methylpyridine (500 mg, 38%) as colorless oil. LC/MS: mass calcd. for C9H12BrNO2: 246.10, found: 246.0 [M]+, 248.0 [M+2]+

The synthetic route of 1003711-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Player, Mark R.; Huang, Hui; Winters, Michael P.; (98 pag.)US2017/291908; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1064783-29-4, Adding some certain compound to certain chemical reactions, such as: 1064783-29-4, name is 5-Chloro-3-fluoro-2-nitropyridine,molecular formula is C5H2ClFN2O2, 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 1064783-29-4.

A vial was charged with 5-chloro-3-fluoro-2-nitropyridine (1 equiv), methyl 2-(morpholin-3-yl)acetate hydrochloride (1.1 equiv), DMF (0.4 M), and triethylamine (3 equiv). The vial was sealed and heated to 80 C for 7 h. The mixture was cooled, then diluted with 1N aq. HC1 and extracted with EtOAc (3x). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was dissolved in acetic acid (0.2 M). Iron (10 equiv) was added, and the resulting mixture was heated to 110 C overnight. The mixture was cooled to room temperature, diluted with EtOAc and filtered through celite. The filter pad was washed successively with EtOAc, DCM, and 20% MeOHIDCM. The combined filtrate was concentrated. The residue was suspended between sat. aq. sodium bicarbonate and EtOAc. The layers were separated, and the aq. layer was extracted with EtOAc (4x). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-90% EtOAc/heptane) to give l0-chloro-4,4a,5,7-tetrahydro- 1H-[ 1 ,4]oxazino[4,3 -d]pyrido[2,3 -b] [1 ,4]diazepin-6(2H)-one (54% yield) as awhite solid. ?HNMR (400 MHz, DMSO-d6) ppm 10.12 (s, 1 H) 8.05 (d, J=2.20 Hz, 1H)7.57(d,J=2.2OHz, 1H)3.75-3.88(m,2H)3.36-3.53(m,3H)3.16-3.29(m, 1H)2.96 (br d, J=ll.13 Hz, 1 H) 2.60-2.69 (m, 1 H) 2.02 (d, J=13.69 Hz, 1 H). LCMS (m/z)(M+H) = 254.0, Rt = 0.89 mm.

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. 1064783-29-4, 5-Chloro-3-fluoro-2-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; KARKI, Rajesh; RAMURTHY, Savithri; RAUNIYAR, Vivek; ROBINSON, Richard; SARVER, Patrick James; (374 pag.)WO2017/103824; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65515-39-1, Adding some certain compound to certain chemical reactions, such as: 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile,molecular formula is C9H10N2O, 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 65515-39-1.

LiAlH4 (48.0 g, 1.27 mol) was added into MTBE (600 mL) portion-wise at room temperature. To the suspension was added 2-methoxy-4,6-dimethylpyridine-3-carbonitrile (Cpd S, 103 g, 0.636 mol) in MTBE/THF (1:1, 600 mL) portion-wise. The reaction mixture was stirred at room temperature for an hour then quenched with water (75 mL). The precipitate was collected by filtration and the solids washed with THF (3*100 mL). The filtrate was concentrated under vacuum to give the 1-(2-methoxy-4,6-dimethylpyridin-3-yl)methanamine (Cpd T), which was used in the next step directly.

According to the analysis of related databases, 65515-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); 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. 885168-20-7, name is 2-Bromo-5-fluoro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Bromo-5-fluoro-4-methylpyridine

Isopropylmagnesiumchloride-lithium chloride complex (1.3 M in THF, 16.4 mmol, 13.0 mL) was added to a solution of 2-bromo-5-fluoro-4-methylpyridine (3. 12 g, 16.4 mmol) in d ry THF ( 16 mL) under argon at 0C. The mixture was stirred for 20 min on ice and ~2 hours at rt (coffee colored solution). The Grignard solution was cannulated into a solution of tert-butyl N-[2- [methoxy(methyl)amino]-2-oxo-ethyl]carbamate (1.75 g, 8.0 mmol) in dry TH F (20 mL) at rt and stirred 1 hour. Quenched with 10% NH4CI (20 mL). The THF layer was dried (Na2S04) and evaporated . Recrystallised from heptane gave Intermediate 21 ( 1.42 g, 66%) as a white solid .

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, 885168-20-7, 2-Bromo-5-fluoro-4-methylpyridine.

Reference:
Patent; LEO PHARMA A/S; LARSEN, Mogens; RITZEN, Andreas; NØRREMARK, Bjarne; GREVE, Daniel Rodriguez; (145 pag.)WO2018/141842; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1149-24-2, Adding some certain compound to certain chemical reactions, such as: 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate,molecular formula is C13H17NO4, 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 1149-24-2.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

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. 1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3430-16-8, Adding some certain compound to certain chemical reactions, such as: 3430-16-8, name is 3-Bromo-5-methylpyridine,molecular formula is C6H6BrN, 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 3430-16-8.

The following are successively introduced into a microwave tube: 469.80 mul (4.07 mmol) of 3-bromo-5-methylpyridine in 20 mL of H2O/DMF: (1/3: v/v), 2.03 mL (5.70 mmol) of tributyl(1-ethoxyvinyl)tin, 57.12 mg (81 .38 mmol) of bis(triphenylphosphine)palladium(ll) chloride, 1.12 g (8.14 mmol) of potassium carbonate. After irradiating with microwaves for 1 hour at 1 10C, the reaction mixture is evaporated to dryness and the residue is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is taken up in a solution consisting of 6 mL of methanol and 1 mL of 1 N hydrochloric acid. After stirring overnight at room temperature, the reaction mixture is evaporated to dryness and the residue is taken up in saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 160 mg of 1-(2-methylpyrid-3-yl)ethanone, the characteristics of which are as follows: LC/MS (method G): ESI+ [M+H]+: m/z 136. tr (min) = 0.38. 1H NMR (300 MHz, delta in ppm, DMSO-d6): 2.58 (s, 3H), 2.61 (s, 3H), 7.38 (m, 1 H), 8.2 (m, 1 H), 8.57 (m, 1 H).

According to the analysis of related databases, 3430-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI; EL-AHMAD, Youssef; FILOCHE-ROMME, Bruno; GANZHORM, Axel; MARCINIAK, Gilbert; MUZET, Nicolas; RONAN, Baptiste; VIVET, Bertrand; ZERR, Veronique; WO2013/190123; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1124-29-4, 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. 1124-29-4, name is 5-Acetylpyridin-2(1H)-one, molecular formula is C7H7NO2, 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.

General procedure: To a solution of 111-3 (1 eq.) in DCM (0.1 mmol/mL) was added boronic acid III-4 (2 eq.), Cu(OAc)2 (1 eq), Pyridine (10 eq.) and Pyridine-N-Oxide (2 eq.), followed by addition of4A molecular sieve (quantity approx. equal to 111-3 ). The reaction mixture was stirred at rt underoxygen atmosphere overnight. After completion of the reaction indicated by TLC, the resultingmixture was filtered and washed with , the filtrate was washed with brine, dried over Na2SO4 andconcentrated. The residue was purified by column chromatography on silica gel to give 111-5.[0316] Compound 10 (61% yield): ?H NMR (DMSO-d6, 400 MHz) (5 8.43 (d, J = 2.4 Hz, 1H), 7.90 (dd, J= 9.6, 2.4 Hz, 1H), 7.39 (d, J= 8.8 Hz, 2H), 7.06 (d, J= 8.8 Hz, 2H), 6.51 (d, J = 9.6 Hz, 1H), 3.81 (s, 3H), 2.41 (s, 3H).

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 1124-29-4, 5-Acetylpyridin-2(1H)-one.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1040682-68-5, 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. 1040682-68-5, name is 1H-Pyrrolo[3,2-c]pyridine-4-carbonitrile, molecular formula is C8H5N3, 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 lH-pyrrolo[3,2-c]pyridine-4-carbonitrile (60.0 mg, 0.42 mmol , 1.0 eq), NIS (52.0 mg, 0.46 mmol, 1.1 eq) in DCM (4.0 mL) was stirred at rt for 2 h. After the reaction was complete, water was added, and the mixture was extracted with EA. The organic layer was washed with water, dried over Na2S04, filtered and concentrated. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide 3-iodo-lH-pyrrolo[3,2-c]pyridine-4-carbonitrile (160 mg, 97%).

According to the analysis of related databases, 1040682-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10177-08-9 , The common heterocyclic compound, 10177-08-9, name is 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C12H9NO3, 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.

EXAMPLE 22 5-Phenyl-2(1H)-pyridinone In the manner described in Example 20, a mixture of 12.4 g. of 1,2-dihydro-2-oxo-5-phenyl-3-pyridinecarboxylic acid (prepared as described in Example 15) and 50 ml. of quinoline yields 8.8 g. of the product of the Example as a gray solid, m.p. 173°-177° C.

The synthetic route of 10177-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4209626; (1980); A;; ; Patent; American Cyanamid Company; US4242515; (1980); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem