Category: pyridine-derivatives

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, molecular weight is 201.02, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromopyridine-2-carboxamide

Example 10 Preparation of 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvcloheylamino)ethyl)picolinamide (Compound-46) and 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvclohexylamino)ethyl)picolinamide (Compound-47)[00144] 5-Bronnopicolinannide 112 (1.29 g, 6.4 mmol) and chloral (1.25 ml_) in dioxane (10 ml_) were heated to 100 0C. The mixture was concentrated to give 5- bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (99%). [00145] A solution of 5-bromo-N-(2,2,2-thchloro-1 -hydroxyethyl)picolinamide 122 (0.83 g, 2.39 mmol) in chloroform (20 ml_) was reacted with PCI5 (0.51 g, 2.33 mmol) at 50 0C for 30 minutes. The mixture was cooled to -78 0C and 4-ethylcyclohexanamine was added (1 g, 7.5 mmol). After 1 hour, the mixture was warmed to room temperature. The reaction mixture was subjected to an aqueous work-up and the product extracted with chloroform. The organic solution was concentrated onto silica gel and the product was eluted (flash: 97:3 hexane:ether then prep-HPLC: Phenomenex Luna column (Sitheta2), 10 micron, 250×50 mm, 150 mL/minute; 3:7 hexanes:dichloromethane) to give first eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcyclohexylamino)ethyl)picolinamide (Compound-46, 106 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.26 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.6 Hz, 1 H), 8.01 (dd, J = 8.4, 2.4 Hz, 1 H), 5.56 (t, J = 9.3 Hz, 1 H), 2.96 (brs, 1 H), 1.80- 1.71 (m, 2H), 1.59-1.21 (m, 10H), 0.85 (t, J = 7.2 Hz, 3H), and second eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4-ethylcyclohexylamino)ethyl)picolinamide (Compound- 47, 166 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.30 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.9 Hz, 1 H),8.01 (dd, J = 8.4, 2.1 Hz, 1 H), 5.50 (t, J = 8.7 Hz, 1 H), 2.68-2.58 (m, 1 H), 2.16-2.07 (m, 1 H), 1.86-1.70 (m, 4H), 1.27-1.01 (m, 6H), 0.96-.087 (m, 1 H) 0.83 (t, J = 7.5 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; NGUYEN, Phong X.; HEIDELBAUGH, Todd M.; CHOW, Ken; GARST, Michael E.; WO2011/19681; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.Product Details of 83766-88-5

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83766-88-5, 2-(tert-Butoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 195044-14-5 ,Some common heterocyclic compound, 195044-14-5, molecular formula is C9H12BrN, 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.

Step-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (200 mg, 0.833 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (214 mg, 0.999 mmol, 1.2 eq) in 1,4 dioxane (3 mL) was added potassium carbonate (230 mg, 1.666 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (31 mg, 0.666 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (30 mg, 0.333 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 95% EtOAc/Hexane to afford 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 32.25%) as off white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,195044-14-5, its application will become more common.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); 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. 1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate. A new synthetic method of this compound is introduced below., COA of Formula: C9H7BrN2O2

A mixture of methyl delta-bromo-lJ-diazabicyclo^^.OJnona^^^jdelta-tetraene-S-carboxylate (0.39 mmol, 100 mg), (6-dimethylaminopyridin-3-yl)boronic acid (0.59 mmol, 98 mg), cesium carbonate (1.57 mmol, 510 mg) and Pd(dppf)Cl2*DCM ( 39 mumol, 32 mg) was dissolved in DMF (3 ml). The mixture was stirred at 80 0C for 1 h and filtered. The filtrate lambdavas subjected to preparative HPLC to give 20 mg of the title compound as a white solid. IH NMR (400 MHz, DMSO-^6) delta ppm 9.24 (s, 1 H) 8.69 (d, J=2.02 Hz, 1 H) 8.38 (s, 1 H) 8.02 (dd, J=8.84, 2.27 Hz, 1 H) 7.61 (s, 2 H) 6.73 (d, J=8.84 Hz, 1 H) 3.89 (s, 3 H) 3.08 (s, 6 H); MS m/z (M+H) 297

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, 1042141-37-6, Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate.

Reference:
Patent; ASTRAZENECA AB; WO2008/91195; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98139-15-2, Adding some certain compound to certain chemical reactions, such as: 98139-15-2, name is 4-Aminopicolinonitrile,molecular formula is C6H5N3, 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 98139-15-2.

Into a 30-mL sealed tube, was placed 2-bromo-5-methoxy-4-[3-(pyrrolidin-l- yl)propoxy]pyridine (314 mg, 1.00 mmol, 1.00 equiv.), 4-aminopyridine-2-carbonitrile (240 mg, 2.01 mmol, 2.00 equiv.), Pd2(dba)3-chloroform (0.1 g, 0.10 equiv.), t-BuXPhos (0.085 g, 0.20 equiv.), Cs2C03 (970 mg, 2.97 mmol, 3.00 equiv.), dioxane (10 mL). The resulting solution was stirred for 16 h at 110 C in an oil bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The organic layer was washed with 1×50 mL of brine, dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (3 mL) was purified by Flash- Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN_Water=l :5 increasing to MeCN_Water=10: l within 120 min; Detector, UV 254 nm. 70 mg product was obtained. This resulted in 70 mg (20%) of 4-([5-methoxy-4-[3- (pyrrolidin-l-yl)propoxy]pyridin-2-yl]amino)pyridine-2-carbonitrile as an off-white solid.

According to the analysis of related databases, 98139-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72648-12-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.72648-12-5, name is 2-Chloro-3-(trichloromethyl)pyridine, molecular formula is C6H3Cl4N, molecular weight is 230.91, as common compound, the synthetic route is as follows.

The 2-chloro-3-trichloromethylpyridine is hydrolyzed to obtain a 2-chloronicotinic acid reaction product, and the reaction formula is as follows

Statistics shows that 72648-12-5 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-3-(trichloromethyl)pyridine.

Reference:
Patent; Weifang Xinlv Chemical Co., Ltd.; Han Zengrui; Sun Zaichen; Han Zhiren; Zhang Jinwang; Jiang Dongsheng; (10 pag.)CN110229098; (2019); A;,
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. 6960-22-1, name is 6-Methylnicotinamide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Methylnicotinamide

Example 4: Synthesis of 106Step 1 :3.00 g (22.0 mmol) 6-methylnicotinamide is dissolved in 10 ml THF under argon-atmosphere and 34 ml (34 mmol; 1.5 eq.) 1 M lithium aluminum hydride in THF are added. After 45 min additional lithium aluminum hydride (1.22 g; 1.5 eq.) in 40 ml THF is added. The reaction mixture is heated to 60C for 24 h under stirring. The reaction mixture is carefully quenched under stirring with isopropyl alcohol, methanol and finally water at 0C. The solvent is removed under vacuum. After addition of 100 ml 2N NaOH solution and 100 ml DCM the white precipitate is centrifuged off and the aqueous layer is extracted 4 times with 60 ml DCM. The combined organic layers are dried over magnesium sulphate and the solvent is removed under reduced pressure yielding 1.57 g (12.9 mmol; 58%) of the amine 2 which is used without further purification for subsequent reaction steps.

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, 6960-22-1, 6-Methylnicotinamide.

Reference:
Patent; JERINI AG; WO2006/128670; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6318-51-0, 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. 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone. A new synthetic method of this compound is introduced below.

0.2 g of (4-chlorophenyl) (2-pyridyl) methanone was dissolved in 2 mL of hydrogen peroxide (mass concentration of 30% aqueous solution) 1.0 mL of acetic acid was added and the reaction was heated to 85 C. for 12 h. The progress of the reaction was monitored by TLC until the reaction was complete. The mixture was saturated with sodium bicarbonate, extracted with dichloromethane, washed, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, Removal of the solvent gave 0.21 g of a white solid in 95% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, and friends who are interested can also refer to it.

Reference:
Patent; Yichang Renfu Pharmaceutical Co., Ltd.; China Three Gorges University; Fu Yigang; Lv Jinliang; Zhou Haifeng; Wang Baigui; Cao Lu; Zheng Huazhang; Tian Luanyuan; Li Shiqun; Li Lie; Du Wentao; (13 pag.)CN106938995; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1132-37-2 , The common heterocyclic compound, 1132-37-2, name is Dipyridin-2-ylmethane, molecular formula is C11H10N2, 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.

[0158] Benzyl potassium 4.0 g (30.5 mmol) was added into a solution of dipyridin-2-ylmethane 5.2 g (30.5 mmol) in 100 mL THF at -70 C. over 10 minutes. The mixture was stirred at ambient temperature for 16 hours after which the bright yellow mixture was filtrated and washed with THF. Solvents were evaporated and the product washed with pentane and evaporated to yield a bright yellow solid which on the basis of the 1H-NMR spectrum in DMSO-d6 was [DPM-K+] [THF]0.5. Yield 5.44 g (73.0%) based the THF complex (Mw=244.35 g mol-1). The product decomposed during ETMS analysis. Elemental analysis calculated for [DPM-K+] [THF]0.5: C 64.6%, H 4.8%, N 12.0%, K 21.9%. Found: C 63.9%, H 5.36%, N 11.46%, K 16.0%. NMR spectra were recorded at +22.7 C., +50 C. and at +70 C. in DMSO-d6. The complex shows fluxional behaviour in NMR with increasing temperature which is caused by the transition between the two resonance structures A and B. The peaks coalescence at +70 C. The singlet bridgehead proton is exchanged slowly with the methyl deuterium of DMSO-d6 which is seen as an appearing triplet in 13C-NMR. 1H-NMR in DMSO-d6 at +70 C. delta: 8.20 and 6.25 (broad coalesence peaks, 2H, from HaHa’), 7.65 (d, 2H, from HdHd’), 6.78 (broad, 2H, from HbHb’), 5.76 (broad, 2H, from HcHc’), 4.62 (S, 1H, exchangeable proton He). 13C-NMR in DMSO-d6 at delta: 160.2, 147.9, 147.8, 132.3, 131.2, 116.9, 114,3, 105.3, 103.3, triplet 87.2 from exchanged CHeDMSO-d6. 13C-CPMAS delta: 163, 150, 138, 119, 109, 82.

The synthetic route of 1132-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andell, Ove; Maaranen, Janne; Hoikka, Jouni; Vanne, Tiina; Rautio, Soile; US2003/225275; (2003); 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 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Chloro-5-nitronicotinic acid

EXAMPLE 16 2-Fluoro-3- nitro-5-trifluoromethylpyridine/2-chloro-3-nitro-5-trifluoromethylpyridine mixture A steel bomb was charged with 6-chloro-5-nitronicotinic acid (4.1 g, 0.02 m), SF4 (21 g) and HF (3.7 ml). The mixture was heated at 90 for eight hours. After cooling to 25, the bomb was vented and the contents poured onto ice. The solution was neutralized with saturated Na2 CO3 solution and extracted with CH2 Cl2. The organic layer was dried over Na2 SO4, filtered and the solution was distilled. A mixture of 2-chloro and 2-fluoro-3-nitro-5-trifluoromethylpyridine (3.3 g) was obtained by distillation at 198-200 (760 mm).

With the rapid development of chemical substances, we look forward to future research findings about 7477-10-3.

Reference:
Patent; Merck & Co., Inc.; US4279913; (1981); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem