Category: pyridine-derivatives

Related Products of 824-51-1, 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. 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

(d) Step 4 6-Methyl-1H-pyrrolo[2,3-b]pyridine (0.066 g, 0.50 mmol) was successively added with acetic acid (0.2 mL), water (0.4 mL), and hexamethylenetetramine (0.098 g, 0.70 mmol), and then the mixture was stirred overnight at 120C in a sealed tube. The reaction mixture was added with water, and then the precipitated solid was collected by filtration to obtain 6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.054 g, 67%). 1H NMR (300 MHz, DMSO-d6) delta 2.55 (s, 3H), 7.16 (d, J = 8.1 Hz, 1H), 8.27 (d, J = 8.1 I Hz, 1H), 8.36 (s, 1H), 10.28 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,824-51-1, its application will become more common.

Reference:
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2,6-Dibromo-4-methylpyridine

A suspension of 2,6-dibromo-4-methylpyridine (2.91 g, 11.6 mmol), pivalic acid (0.25 mL, 2.11 mmol), potassium carbonate (2.92 g, 21.1 mmol), thiazole (0.75 mL, 10.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.49 g, 0.42 mmol) in N,N- dimethylacetamide (23 mL) was heated at 130 C for 18 hours. The reaction mixture was diluted with ethyl acetate, filtered through a pad of CELITE, and washed with water (2x). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/hexanes) to afford 2-bromo- 4-methyl-6-(l,3-thiazol-5-yl)pyridine. 1H NMR (600 MHz, CDC13) delta 8.80 (s, 1H), 8.29 (s, 1H), 7.38 (s, 1H), 7.19 (s, 1H), 2.34 (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, 73112-16-0, 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 54957-86-7, 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.54957-86-7, name is 2,3-Dichloro-6-methylpyridine, molecular formula is C6H5Cl2N, molecular weight is 162.0166, as common compound, the synthetic route is as follows.

A mixture of 8,1 (1 .70 g, 10,51 mmol), Zn(CN)2 (0.74 g, 6.30 mmol) and Zn (0.031 g, 0,47 mmol) in DMF (10.5 mL) is degassed (B. Van Wagenen, US2003/55085). PdC^dppfj-CHzCIs adduct (0.189 g, 0.231 mmol) is added and the solution is again degassed then is heated at 125C for 5 h. The crude mixture is diluted with EtOAc (150 mL) and the mixture is filtered through diatomaceous earth (washing the cake with EtOAc (25 mL)). The filtrate is washed twice with a mixture of water and saturated NaHC03 solution (3/1 ) and with brine, then dried (Na2S04), filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (10-10Q%EtQAc:Hex) to give 8.2; MS: m/z = 153.1/155.1 (MH+); 1 H NMR (400 MHz, CDCI3) delta ppm 2.60 (s, 3 H), 7.34 (d, J=8.22 Hz, 1 H), 7.73 (d, J=8.61 Hz, 1 H).

Statistics shows that 54957-86-7 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloro-6-methylpyridine.

Reference:
Patent; UNIVERSITE DE MONTREAL; SIMONEAU, Bruno; CHANTIGNY, Yves; YEH, Jonathan; SAUVAGEAU, Guy; MARINIER, Anne; (94 pag.)WO2019/87129; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16744-81-3 ,Some common heterocyclic compound, 16744-81-3, molecular formula is C7H7NO2, 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.

To a solution of 4-methoxypicolinaldehyde (1.01 g, 7.36 mmol) in DCM (40 mL) was added trimethylsilanecarbonitrile (1.106 mL, 8.84 mmol). The mixture was stirred at room temperature overnight. The mixture was concentrated down to afford a light brown oil, which was treated with conc. sulfuric acid (5 mL, 94 mmol) for 4 hours, then poured the reaction mixture into ice, and adjusted the PH to 9 using NH4OH. The mixture was concentrated down with Celite®, purified by silica column( CombiFlash®, 40g column) using 0-10percent MeOH/DCM to afford 2-hydroxy-2-(4-methoxypyridin-2-yl)acetamide (748 mg, 4.11 mmol, 55.7percent yield) as a yellow solid. LCMS m/z = 183.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16744-81-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
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Pyridine | C5H5N – PubChem

Related Products of 56673-34-8, 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 56673-34-8 as follows.

2.0 g of 5-Bromo-pyridine-2-thiol (compound C1 ) are dissolved in 40 ml of carbon tetrachloride and 8 ml of water. Subsequently, the suspension is cooled in an ice bath and chlorine gas is passed into the reaction mixture for 20 min (flow: 35 ml/min). Thereafter, nitrogen is passed into the yellow solution to remove excess chlorine. Subsequently, the mixture is diluted with 150 ml of dichloromethane and extracted with 50 ml of brine. The organic layer is separated, dried using Na2SO4, filtered with suction, and evaporated to dryness to afford 2.70 g of the title compound as light yellow needles. M. p. 8O0C. GC-MS: 254.8/256.8/258.8 (77:100:25; M+). TLC: Rf = 0.84 (dichloromethane/ethanol 20:1 parts by volume).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56673-34-8, its application will become more common.

Reference:
Patent; ALTANA PHARMA AG; WO2007/39580; (2007); 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. 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 135450-23-6

[00369] 6-((((tert-Butoxy)carbonyl)amino)methyl)picolinonitrile (P31): To a solution of commercially available chloride P30 (9.66 g, 63.3 mmol) in DMF (400 mL) at ambient temperature was treated with potassium phthalimide (11.7 g, 63.3 mmol). After stirring for 5 h, the mixture was concentrated under vacuum. The remaining mixture was taken up in H20 (200 mL) and was filtered to collect the solid. The solid was washed with H20 (100 mL) and THF (100 mL) to obtain the desired phthalimide derivative (11.5 g, 69%) and was moved forward without further purification. To a solution of the crude phthalimide derivative (5.84 g, 22.2 mmol) in THF/MeOH (200 mL, 1:1, v/v) at ambient temperature was treated with hydrazine monohydrate (1.18 mL, 24.4 mmol). After 2 h, 1.0 M HC1 (24.5 mL) was added to the mixture and was stirred for another 3 h before concentrating the reaction mixture under vacuum. The remaining residue was taken up in H20 (200 mL) and the unwanted solid was removed through filtration. The filtrate was concentrated and placed under vacuum to remove the remaining H20. The crude solid was taken up in CH2C12 (175 mL) and triethylamine (9.28 mL, 66.6 mmol) and Boc2O (4.86 g, 24.4 mmol) was added. After stirring for 12 h at room temperature, the reaction was quenched with a saturated solution of NaHCO3 (200 mL), extracted with CH2C12 (3 x 150 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified using flash chromatography (10% to 45% ethyl acetate in hexanes) to provide the aryl pyridine ?IN? fragment (2.24 g, 43%): ?H-NMR (CDC13, 400 MHz) oe 7.78 (t, J = 7.6 Hz, 1H), 7.56 (d, J = 7.6 Hz, 1H), 7.49 (d, J= 8.0 Hz, 1H), 5.51 (s, 1H), 4.44 (d, J= 5.6 Hz, 2H), 1.43 (s, 9H); ?3C-NMR (CDC13, 100 MHz) 160.1, 155.9, 137.6, 133.0, 127.0, 125.1, 117.1, 79.9, 45.5, 28.3; JR (neat) 3347, 2979, 2934, 2239, 1699, 1518, 1453, 1250, 1170, 862; HRMS (ESI) mlz calcd for C12H15N3NaO3 [M+Na1 256.1062, found 256.1062.

The synthetic route of 135450-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLORADO STATE UNIVERSITY RESEARCH FOUNDATION; DANA-FARBER CANCER INSTITUTE, INC.; UNIVERSITY OF NOTRE DAME DU LAC; WILLIAMS, Robert, M.; BRADNER, James, E.; CLAUSEN, Dane; WIEST, Olaf, G.; NEWKIRK, Tenaya, L.; BOWERS, Albert, A.; GUERRA, Jennifer, Marie; (144 pag.)WO2016/144665; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 24207-22-5 ,Some common heterocyclic compound, 24207-22-5, molecular formula is C7H8BrNO, 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.

[0125] 2-Bromo-3-methoxy-6-methylpyridine (XXXXV) 760 mg (3.76 mmol) was dissolved in 15 ml of water, and to the resulting solution was added potassium permanganate (KMnO4) (1.49 g, 9.40mmol) and the mixture was heated at 80 C for 3 hrs. After TLC was conducted, pH was adjusted to 4 with 10% hydrochloric acid (HCl) and filtration was conducted with celite. The filtrate was extracted with 50 ml of ethylacetate (EA). The organic layer was treated with magnesium sulfate (MgSO4) and filtered, and the solution was concentrated to give the title compound as a white solid (665 mg, 2.87 mmol, 75 %) without purification. 1H NMR (400 MHz, DMSO-d6) delta 13.22 (s, OH), 8.05 (d, J = 8.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 4.02 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24207-22-5, its application will become more common.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66909-38-4, 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. 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, 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.

6-Chloro-4-methylpyridin-3-amine (22.0 g, 154.9 mmol) was dissolved in DMF (150 mL) and treated with NIS (41.8 g, 185.9 mmol). The reaction mixture was stirred at rt overnight, then water (200 mL) was added, and the mixture was extracted with EtOAc (3×200 mL). The combined organics were concentrated in vacuo and the residue was subjected to silica gel flash chromatography eluting with Et2O-EtOAc to give 6-chloro-2-iodo-4-methylpyridin-3-amine. 1H NMR (DMSO-d6, 400 MHz): delta7.11 (s, 1H), 5.23 (s, 2H), 2.15 (s, 3H) ppm

According to the analysis of related databases, 66909-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); 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. 87674-15-5, name is 1-(3-Fluoropyridin-4-yl)ethanol, the common compound, a new synthetic route is introduced below. Formula: C7H8FNO

a) 4-(l-Chloroethyl)-3-fluoropyridinel-(3-fluoropyridin-4-yl)ethanol (0.8 g, 5.7 mmol) was treated with thionyl chloride (5 mL) and the resulting mixture was heated to 80 C for 2 h. Water (10 mL) and sat. sodium bicarbonate (aq., 10 mL) was added. The product was extracted with DCM (three times). The combined organic extracts were washed with brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash column chromatography (eluent heptane: ethyl acetate gradient) to yield 0.36 g (39% yield) of the title compound. 1H NMR (300 MHz, CDCl3) 8.45 (m, 2H), 7.50 (m, IH), 5.34 (q, IH), 1.83 (d, 3H).

The synthetic route of 87674-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/39138; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 83766-88-5, 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine. A new synthetic method of this compound is introduced below.

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.

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