Pyridine-derivatives

Electric Literature of 6443-85-2, 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.6443-85-2, name is 2-(Pyridin-3-yl)acetonitrile, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.

Example 1A trans-2-(3-Pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile To a stirred solution of 400 g (2.3 mole) 3,5-dichlorobenzaldehyde in 11.4 liters absolute ethanol were added 283.5 g (2.4 mole) 3-pyridylacetonitrile and 720.9 g of K2 CO3. Within 2 minutes of the K2 CO3 addition, a solid precipitate formed. The reaction mixture was stirred about 2.5 hours. Water (22.9 liters) was added to the stirred reaction mixture. After stirring for 1 hour, the mixture was filtered and the filter cake was washed with water (10 liters), dried and recrystallized from isopropanol. Five hundred thirty four g (85% yield) of trans-2-(3-pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile were obtained, m.p. 150-151 C.

The chemical industry reduces the impact on the environment during synthesis 6443-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Rhone-Poulenc Rorer International (Holdings) Inc.; US5418245; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58530-53-3, 2,4-Dibromopyridine, 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, HPLC of Formula: C5H3Br2N, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3Br2N

Step 1: ethyl 2-[(4-bromopyridin-2-yl)amino]-1,3-oxazole-5-carboxylate To a mixture of 2-amino-oxazole-5-carboxylic acid ethyl ester (0.483 g, 3.09 mmol), tris(dba)dipalladium (O) (0.070 g, 0.077 mmol), xantphos (0.120 g, 0.208 mmol) and cesium carbonate (1.95 g, 5.98 mmol) in 1,4-dioxane (15.0 mL, 192 mmol) was added 2,4-dibromopyridine (1.078 g, 4.55 mmol). The reaction was heated in the microwave at 115 C. for 1 h. The reaction was diluted with DCM (30 mL), silica gel was added to the mixture (11 g) and the solvents were removed to absorb material onto the silica. Purification of sample by column chromatography to afford ethyl 2-[(4-bromopyridin-2-yl)amino]-1,3-oxazole-5-carboxylate (0.561 g, 58%). 1H NMR (400 MHz, DMSO-d6) delta 11.64 (s, 1H), 8.34 (s, 1H), 8.21 (d, J=5.3 Hz, 1H), 7.90 (s, 1H), 7.32 (dd, J=5.3, 1.6 Hz, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H) and ethyl 2-[(2-bromopyridin-4-yl)amino]-1,3-oxazole-5-carboxylate (0.13 g, 14%). 1H NMR (400 MHz, DMSO-d6) delta 11.63 (s, 1H), 8.23 (d, J=5.7 Hz, 1H), 8.01-7.84 (m, 2H), 7.47 (dd, J=5.7, 2.0 Hz, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H).

The synthetic route of 58530-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

To a mixture of tert-butyl 8-bromo-5-methyl-3,4-dihydro-lH-pyrido[4,3-delta]indole- 2(5H)-carboxylate (0.48 g, 1.3 mmol), 4-(benzyloxy)pyridin-2(lH)-one (264 mg, 1.31 mmol), 8-hydroxyquinoline (29 mg, 0.20 mmol), K2CO3 (217 mg, 1.57 mmol) and CuI (38 Attorney’s Docket 2882.023B mg, 0.20 mmol) was added DMSO (5 mL). The reaction mixture was degassed and backfilled with N2. The reaction mixture was heated to 130 0C and stirred at 130 0C overnight. After it was cooled, the mixture was filtered through a layer of Celite. The filtrate was diluted with CH2Cl2, washed with H2O and 5% LiCl, dried with Na2SO4, filtered, and concentrated. Purification by flash column chromatography (silica gel, 5% CH3OH in CH2Cl2) gave the title compound (0.28 g, 44%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 7.36-7.29 (m, 8H), 7.13 (d, J= 8.0 Hz, IH), 6.09 (d, J= 2.0 Hz, IH), 6.03 (dd, J = 7.5, 2.0 Hz, IH), 5.05 (s, 2H), 4.61 (s, 2H), 3.84 (m, 2H), 3.66 (s, 3H), 2.82 (m, 2H), 1.49 (s, 9H); ESI MS m/z 486 [M + H]+.

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 118650-08-1, Adding some certain compound to certain chemical reactions, such as: 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate,molecular formula is C8H8BrNO2, 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 118650-08-1.

(5-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 58 mg, 0.25 mmol), palladium acetate (3.8 mg, 0.017 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (14 mg, 0.034 mmol), potassium phosphate (108 mg, 0.51 mmol) and water (0.4 mL) were added to a solution of 2-(4-{1-ethyl-1-[3-methyl-4-(4-trimethylsilanyloxy-tetrahydro-thiopyran-4-ylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 136-(4); 100 mg, 0.17 mmol) in toluene (4 mL). The mixture was stirred in a nitrogen stream at 110C for two hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate = 1:3) to give the title compound (82 mg, 79%). 1H-NMR (chloroform-d): 0.23 (s, 9H), 0.65 (t, 6H, J=7.3Hz), 1.96-2.06 (m, 2H), 2.12 (q, 4H, J=7.3Hz) 2.16-2.24 (m, 2H), 2.24 (s, 3H), 2.41 (s, 3H), 2.7-2.8 (m, 2H), 2.8-2.9 (m, 2H), 3.67 (s, 2H), 3.72 (s, 3H), 6.96-7.12 (m, 5H), 7.30 (d, 1H, J=8.0Hz), 7.60-7.64 (m, 1H), 8.47 (d, 1H, J=1.8Hz), 8.52 (d, 1H, J=1.8Hz).

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. 118650-08-1, Methyl 2-(5-bromopyridin-3-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109-04-6, 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 109-04-6, name is 2-Bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a flame-dried Schlenk tube equipped with a magnetic stir bar was loaded alkyl bromide (0.15 mmol, 100 mol%, solid), halogenated pyridine (0.30 mmol, 300 mol%, solid), ligand (0.015 mmol, 10 mol%), zinc powder (0.45 mmol, 300 mol%). The tube was capped with a rubber septum and moved to a dry glove box, at which NiBr2 (0.015 mmol, 10 mol%), MgCl2 (0.15 mmol, 100 mol%) and Bu4NBr (0.075 mmol, 50 mol%) were added. Then the tube was moved out of the glove box. Alkyl bromide (0.15 mmol, 100 mol%, liquid), halogenated pyridine (0.30 mmol, 300 mol%, liquid), pyridine (0.15 mmol, 100 mol%) and DMA(1.0 mL) were added via syringe. After the reaction mixture was allowed to stir overnight under N2 atmosphere at 30 C, it was directly loaded onto a silica column without work-up. The residue in the reaction vessel was rinsed with small amount of DCM or eluent. Flash column chromatography provided the product as solid or oil.

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 109-04-6, 2-Bromopyridine.

Reference:
Article; Liu, Huiyan; Liang, Zhuye; Qian, Qun; Lin, Kunhua; Synthetic Communications; vol. 44; 20; (2014); p. 2999 – 3007;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 894074-85-2, 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.894074-85-2, name is Ethyl 2-chloro-5-methylnicotinate, molecular formula is C9H10ClNO2, molecular weight is 199.63, as common compound, the synthetic route is as follows.

A mixture of ethyl 2-chloro-5-methylnicotinate (14.7 g) , 2, 2′ -azobis (isobutyronitrile) (1.31 g) , N- bromosuccinimide (17.1 g) and carbon tetrachloride (200 ml) was heated at 900C for 5 hours. After an aqueous saturated sodium chloride solution (100 ml) was added to the reaction mixture, this was extracted with ethyl acetate, and the ethyl acetate layer was washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the desired product (10.5 g) as an oil. 1H-NMR (CDCl3) delta 1.4 – 1.5 (3H, m) , 4.3-4.5 (4H, m) , 7.97 (IH, d) , 8.19 (IH, d) .

The chemical industry reduces the impact on the environment during synthesis 894074-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2006/64944; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19798-77-7, 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. 19798-77-7, name is 4-Amino-3-chloropyridine. A new synthetic method of this compound is introduced below.

To a (100 ml_) round bottom flask was added 2-(5-iodo-3-methyl- 4-oxo-3H-pyrrolo[2,3-d]pyrimidin-7(4H)-yl)acetic acid (1.2 g, 3.60 mmol), HATU (1.370 g, 3.60 mmol) and 4-amino-3-chloropyridine (0.695 g, 5.40 mmol). N,N- dimethylformamide (DMF) (Volume: 7 mL) was added. The mixture was stirred at room temperature for 2 hrs after which an additional amount HATU (0.5 eqv) was added until reaction was judged complete by LCMS. A mixture of EtOAc/Hexanes (50 ml, 1 :4) was added and the crude mixture stirred for an additional 5 minutes. The top layer was decanted and the resulting mixture was treated with 50 mL of water. The resulting precipitate was filtered, dried under vacuum at 45-50C to afford the desired product (1.582g, 95% yield); LCMS [M+H]+ 444.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19798-77-7, 4-Amino-3-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; PRAKESCH, Michael; JOSEPH, Babu; MORIN, Justin-Alexander; (441 pag.)WO2019/153080; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7153-08-4, 3,5-Diiodopyridin-4-ol, 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, Safety of 3,5-Diiodopyridin-4-ol, blongs to pyridine-derivatives compound. Safety of 3,5-Diiodopyridin-4-ol

Example 405 N-[5-{7-(4-tert-Butylphenyl)furo[3,2-c]pyridin-2-yl}pyridin-3-yl]acetamide Step 1: Synthesis of N-{5-(7-iodofuro[3,2-c]pyridin-2-yl)pyridin-3-yl}acetamide [0743] A solution prepared by dissolving 3,5-diiodopyridin-4-ol (5.0 mmol), N-(5-ethynylpyridin-3-yl)acetamide (6.0 mmol) and copper(II) oxide (3.5 mmol) in anhydrous pyridine (30 ml) was stirred under reflux for 6 hours. The reaction mixture was cooled to room temperature, filtered through Celite, and concentrated under reduced pressure to yield brown oil. The residue was diluted with ethyl acetate, washed with aqueous ammonia, water and brine, in sequence, which was then dried over anhydrous magnesium sulfate and filtered. After the filtrate was concentrated, the residue thus obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1, v/v) to obtain the title compound as light brown oil (yield: 49%).

The synthetic route of 7153-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; Seo, Hyoung Sig; Kim, Tae Kyun; Lee, Hyun Joo; Kim, Dong Hoon; Lee, Gyu Jin; Park, Jun Chul; Gal, Ji Yeong; Kim, Tae-hoon; Hyun, Kwan Hoon; Ahn, Kyoung Kyu; Park, Kaapjoo; Nam, Su Youn; Lee, Ge Hyeong; Lim, Hee Jong; US2015/191478; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-37-0, 2,5-Dibromo-3-nitropyridine, 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, Product Details of 15862-37-0, blongs to pyridine-derivatives compound. Product Details of 15862-37-0

Step 1: Methyl 4-(5-bromo-3-nitropyridin-2-yl)benzoate To a mixture of 2,5-dibromo-3-nitropyridine (2.00 g, 7.09 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (1.28 g, 7.09 mmol) Pd(dppf)C12 (0.36 g, 0.50 mmol) in THF (30 mL) was added tripotassium phosphate (3M in water) (7.09 mL, 21.3 mmol). The reaction mixture was purged with N2 (3x) and then stirred at 80 C for 3 h. The aqueous layer was separated. The organic layer dried with Na2SO4, filtered through a small plug of Celite washing with EtOAc and concentrated. The crude residue waspurified using ISCO silica gel chromatography (120 g column, gradient from 0% to 50% EtOAc/CH2C12) to give the title compound (1.64 g, 69%) as a white solid. Step 1: 5-Bromo-2-(2-fluoro-5-methanesulfonylphenyl)-3-nitropyridineFollowing procedures analogous to those described for methyl 4-(5-bromo-3-nitropyridin-2-yl)benzoate, 2-(2-fluoro-5 -methanesulfonylphenyl)-4,4,5 ,5 -tetramethyl1,3 ,2-dioxaborolane (500 mg, 1.66 mmol) was converted to the title compound (325 mg,52%). ?H NMR (500MHz, CDC13) oe 9.02 (d, J=2.0 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H), 8.34(dd, J6.5, 2.4 Hz, 1H), 8.10 (ddd, J8.7, 4.7, 2.4 Hz, 1H), 7.34 (dd, J=9.4, 8.8 Hz, 1H),3.15 (s, 3H); LCMS (M+H) = 375; HPLC RT = 1.977 mm (Column: Chromolith ODS S54.6 x 50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B:90:10 MeOH:water with 0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 mm; Flow: 4 mL/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-37-0, 2,5-Dibromo-3-nitropyridine, and friends who are interested can also refer to it.

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

Electric Literature of 189278-27-1, 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. 189278-27-1, name is 2-Bromo-6-(trifluoromethyl)pyridine, molecular formula is C6H3BrF3N, 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.

Example 30 (3aR,4R,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-ol (3aR,4R,6aS)-Octahydrocyclopenta[c]pyrrol-4-ol (1.65 g, 12.97 mmol) from Example 29, 2-bromo-6-(trifluoromethyl)pyridine (3.66 g, 16.22 mmol) and triethylamine (7.23 mL, 51.9 mmol) were combined in ethanol (7.23 mL). The reaction was heated at 80 C. for 24 hours and the solvent was concentrated in vacuo. The resulting residue was purified by silica gel chromatography using 0-40% ethyl acetate/hexane as eluent to give the title compound and the title compound of Example 31: 1H NMR (500 MHz, pyridine-d5) delta ppm 7.47 (t, J=7.9, 1H), 6.94 (d, J=7.2, 1H), 6.53 (d, J=8.6, 1H), 6.38 (d, J=4.1, 1H), 4.47-4.38 (m, 1H), 4.12 (dd, J=11.0, 4.3, 1H), 3.70-3.63 (m, 1H), 3.53 (t, J=10.0, 1H), 3.38 (dd, J=10.4, 4.6, 1H), 2.80-2.73 (m, 1H), 2.72-2.64 (m, 1H), 1.97-1.74 (m, 3H), 1.64-1.56 (m, 1H); MS (ESI+) m/z 273 (M+H)+.

According to the analysis of related databases, 189278-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; US2011/294854; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem