Category: pyridine-derivatives

Electric Literature of 84249-14-9, 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.84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.

To a solution of 258-1 (2.477 g, 14.3 mmol) in THF (40 ml) is added AU-1 (2.20 ml, 15.8 mmol), and the mixture is heated at reflux for 2 h. A solution of TEA (5 ml) in ethanol (15 ml) is added. After stirring for 2 h at 80 C, the mixture is cooled to ambient temperature, and filtered. The residue is dissolved in EtOAc, washed with water, and concentrated. The residue is purified on SiO2 (0-70% EtOAC in heptane) to give 258-2.

Statistics shows that 84249-14-9 is playing an increasingly important role. we look forward to future research findings about 2-Amino-4-bromopyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ABEYWARDANE, Asitha; BRUNETTE, Steven Richard; BURKE, Michael Jason; KIRRANE, Thomas Martin, Jr.; MAN, Chuk Chui; MARSHALL, Daniel Richard; PADYANA, Anil Kumar; RAZAVI, Hossein; SIBLEY, Robert; SMITH KEENAN, Lana Louise; SNOW, Roger John; SORCEK, Ronald John; TAKAHASHI, Hidenori; TAYLOR, Steven John; TURNER, Michael Robert; YOUNG, Erick Richard Roush; ZHANG, Qiang; ZHANG, Yunlong; ZINDELL, Renee M.; WO2014/14874; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1072-97-5 ,Some common heterocyclic compound, 1072-97-5, molecular formula is C5H5BrN2, 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.

2-Amino-5-bromopyridine (2) (20 g, 115.6 mmol) was added to a 500-mL three-necked flask at room temperature, followed by the addition of anhydrous ethanol (200 mL) and sodium bicarbonate (24.3 g, 289.0 mmol). Then ethyl 3-bromopyruvate (33.8 g, 173.4 mmol) was slowly added dropwise with stirring. After the completion of the dropwise addition, the reaction mixture was heated to 85 C and refluxed for 8 h. After the reaction completed, the solvent was evaporated to dryness under reduced pressure. Then proper water was added the pH was adjusted to 8 to 9 with sodium hydroxide. The solution was stirred well and filtered. The filter cake was washed with methyl tert-butyl ether (15 mL×3) to obtain 3 (25.1 g, yield 80.6%) as a yellow-brown powder. 1H NMR (400 MHz, chloroform-d) delta 8.32 (s, 1H, Ar-H), 8.16 (s, 1H, Ar-H), 7.61 (d, J = 9.6 Hz, 1H, Ar-H), 7.33 (dd,J = 9.6, 1.8 Hz, 1H, Ar-H), 4.48 (q, J = 7.1 Hz, 2H, -OCH2-), 1.46 (t, J = 7.1 Hz, 3H,-CH3). MS (ESI): m/z 270.0 [M+H]+.

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. 1072-97-5, 5-Bromopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qin; Long; Zhu; Zhou; Chai; Zhao; Journal of Structural Chemistry; vol. 60; 12; (2019); p. 1917 – 1924; Zh. Strukt. Kim.; vol. 60; 12; (2019); p. 2002 – 2009,8;,
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.18437-58-6, name is 4-Amino-2-picoline, molecular formula is C6H8N2, molecular weight is 108.14, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of (E)-methyl 3-(2-(2-chloropyrimidin-5-yl)vinyl)-4-fluoro- 5-methoxybenzoate (232 mg, 0.72 mmol) in 1,4-dioxane (12 mL) were added 2-methylpyridin-4-amine (93 mg, 0.86 mmol), palladium( II )acetate (16 mg, 0.072 mmol), Xantphos (83 mg, 0.14 mmol) and Cs2C03 (703 mg, 2.16 mmol). Then the mixture was stirred under microwave at 150C for 20 min. The mixture was then concentrated and purified via ISCO (eluted with MeOH in DCM 0%~15%) directly to give a yellow solid (143 mg, 50.4% yield). MS (m/z): 395.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18437-58-6, 4-Amino-2-picoline, and friends who are interested can also refer to it.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; ZHANG, Weihan; LI, Jinshui; WO2014/139465; (2014); 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 1480-65-5, name is 5-Chloro-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 1480-65-5

General procedure: To an oven dried glass vessel capable of being sealed with a Teflon cap (for microwave vials) was added XPhos?Pd-G2 (11.8mg, 15mumol), XPhos (14.3mg, 30mumol), B2(OH)4 (203mg, 2.25mmol), KOAc (441mg, 4.5mmol), and halide (only if a solid). The vessel was sealed, evacuated, and filled with an inert gas (4×). EtOH (15mL, degassed) was added via syringe followed by the addition of ethylene glycol (280mg, 250muL, 4.5mmol) and the halide (1.5mmol) in a similar manner (if applicable). The reaction was heated to the specified temperature until the starting material was consumed (as monitored by GC). The reaction was cooled, and a needle attached to a manifold under an inert atmosphere was inserted into the septum, and 3equiv of degassed K3PO4 (1M, 4.5mL, 4.5mmol) was added via syringe, and the reaction was allowed to sit for 5min. Then the second halide was added in a similar manner (as a solution in 500muL of degassed EtOH or THF if a solid). The manifold needle was removed, and the reaction was heated to the specified temperature for 24h. The reaction was cooled to rt and filtered through a very thin pad of Celite, eluting with 5×10mL of EtOAc, and then concentrated. The crude reaction was dissolved in EtOAc (10mL), transferred to a separatory funnel, and then saturated NaHCO3 (10mL) was added. The aqueous layer was extracted with EtOAc (3×5mL). The combined organics were dried (Na2SO4), filtered, and concentrated. The desired compound was purified by silica gel column chromatography, eluting with EtOAc/hexane.

With the rapid development of chemical substances, we look forward to future research findings about 1480-65-5.

Reference:
Article; Molander, Gary A.; Trice, Sarah L.J.; Tschaen, Brittany; Tetrahedron; vol. 71; 35; (2015); p. 5758 – 5764;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53014-84-9, 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. 53014-84-9, name is 2-Methyl-5-formylpyridine. A new synthetic method of this compound is introduced below.

Ethyl cyanoacetate (607 mg, 5,36 mmol), 6-methylpyridine-3~carbaldehyde (650 mg, 5.36 mmol), piperidine (0.26 mL) and acetic acid (48 mg) were siiiTed in eihanol (10 mL) at RT for 16 h. The mixture was diluted in TBME/Heptane and cooled on dry ice to induce precipitation. Solid formed was filtered off and washed with peniane to give the title compound as a white solid (0.89 g, 70%), 1H NMR (500 MHz, Chlorofonn-d) delta 8.78 (d, J – 2.3 Hz, 1H) 8.51 (dd, J – 8.3, 2.4 Hz, 1H), 8.23 (s, 1H), 7.32 (d, J = 8.3 Hz, 1 H), 4.40 (q, J = 7.1 Hz, 2H), 2.65 (s, 3H), 1.40(t, J – 7, 1 Hz, 3H). LCMS Method C: rt 1.08 min; 91 % m/z 216.9 (MH?),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53014-84-9, 2-Methyl-5-formylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; EVOTEC INTERNATIONAL GMBH; GAMPE, Christian, M.; KAHNE, Daniel, Evan; KAHNE, Suzanne, Walker; QIAO, Yuan; EAST, Stephen; PARKES, Alastair, L.; SOUTHEY, Michelle; HUNTER, James; WHITTAKER, Mark; ARTHUIS, Martin; (359 pag.)WO2016/191658; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 82671-06-5, 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid, 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, Formula: C6H2Cl2FNO2, blongs to pyridine-derivatives compound. Formula: C6H2Cl2FNO2

CDI (35.6 g, 220 mmol) was added portionwise to a solution of C1 (42 g, 200 mmol) in THF (400 mL).The mixture was stirred for 5 min, protected with Ar, heated to 50 C, and reacted for 1 h.After LC-MS monitoring, the starting material disappeared, and the reaction mixture was diluted with toluene (100 mL) and concentrated to half of the original volume.The resulting mixture was cooled to 0 C and ammonium hydroxide (55 mL, 400 mmol) was slowly added.The reaction was carried out for 10 min at room temperature, diluted with EA (200 mL) and washed with water (100 mL*3).The organic layer was dried over anhydrous Na 2 SO 4 and dried. PE/EA (10/1, 200 mL) beaten, filtered,The remaining mother liquor was concentrated to half of the initial volume, cooled to 0 C, and the solid was again precipitated and filtered.The two crops were combined to give a pale-yellow solid product 74-1 (22.10 g, yield 53%).The primary product was used in the next reaction without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,82671-06-5, 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Weijing Biological Pharmaceutical (Shanghai) Co., Ltd.; Fan Houxing; Xie Yuli; (72 pag.)CN110256421; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 59782-85-3, Adding some certain compound to certain chemical reactions, such as: 59782-85-3, name is 2,5-Dichloronicotinic acid,molecular formula is C6H3Cl2NO2, 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 59782-85-3.

Lithium 2-amino-5-chloronicotinateA solution of 2,5-dichloronicotinic acid (20.2 g, 0.105 mol) in methanol (500 ml_) was cooled to 00C and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over -30 min. The reaction mixture was stirred at 00C for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to room temperature, and the reaction was allowed to stir for an additional 2 days at room temperature. The solvent was removed under reduced pressure to give an off-white residue. The residue was dissolved in Et2O (-500 mL) and the resulting solution was washed successively with satd. aq. NaHCO3 solution (-300 mL), water (-300 mL), and brine (-300 mL). The organic layer was separated, dried over anhydrous MgSO4, and filtered. Removal of the solvent under reduced pressure yielded methyl 2,5-dichloronicotinate (21.0 g, 97%) as a white solid.

According to the analysis of related databases, 59782-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/91428; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 115473-15-9, 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 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

2. Take the reaction tube, rotor, air head in the oven full drying, dryer cooling.CH3CN (1 mL) was stirred with molecular sieve at room temperature for 10 min under argon.Protected in argonFollowed by the addition of material C:(0.14 mmol, 27.5 mmol), Na2CO3 (0.29 mmol, 31.0 mg)Finally, alpha-cyclopropylcarbonyl-2-fluorobenzyl chloride (0.117 mmol, 25.0 mg, 20 muL) was slowly added and heated at 60 C for 12 h (reflux condenser). The solvent was spin dried and the column was directly chromatographed,The product was obtained as a white solid D (20.2 mg, yield 52%.)

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 115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride.

Reference:
Patent; Lanzhou University; Zhang Fumin; Peng Rui; Tang Shizhong; (9 pag.)CN107056803; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 524955-09-7, Adding some certain compound to certain chemical reactions, such as: 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline,molecular formula is C12H11ClN2O, 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 524955-09-7.

General procedure: A mixture of (E)-N’-(2-cyano-4-nitrophenyl)-N,N-dimethylformimidamide (5) (2.99g, 13.7 mmol) and appropriate aniline (15.1 mmol) in glacial acetic acid (15.0mL) was refluxed for 2 h. The acetic acid was evaporated and the solid waswashed with water and diethyl ether and dried to afford the titled compounds.

According to the analysis of related databases, 524955-09-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Elkamhawy, Ahmed; Farag, Ahmed Karam; Viswanath, Ambily Nath Indu; Bedair, Tarek M.; Leem, Dong Gyu; Lee, Kyung-Tae; Pae, Ae Nim; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5147 – 5154;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 24484-93-3, Adding some certain compound to certain chemical reactions, such as: 24484-93-3, name is Methyl 4-chloropicolinate,molecular formula is C7H6ClNO2, 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 24484-93-3.

13 g (62.5 MMOL) 1 are dissolved together with 2.98 g (31.24 MMOL) dry magnesiumchloride in THF. After 5 min 110 ML METHYLAMIN-SOLUTION (2M in THF) are added dropwise within 10 min and the suspension stirred for 2 h at room temperature. 120 ml water und 63 mL 1 M HCI-SOLUTION are added and the mixture is extracted three times with ethyl acetate. The combined organic phases are washed with brine, dried with NA2SO4, filtered and evaporated. Yield : 10.5 g (98. 5 %) 2, colourless oil.

According to the analysis of related databases, 24484-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; WO2005/4864; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem