Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 175204-80-5, 3-Amino-4-(trifluoromethyl)pyridine, 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, 175204-80-5, blongs to pyridine-derivatives compound. Computed Properties of C6H5F3N2

The 3-amino-4-trifluoromethylbenzoate methylpyridinio (5g, 30.8mmol) was added to the 50% sulfuric acid (50 ml) at -5 C dropped in NaNO 2 (2.55g, 37 . 0mmol) aqueous solution (10 ml). Transfer to is omitted the reaction at room temperature 30 minutes, then to the reaction system by adding concentrated sulfuric acid (25 ml), heating to 110 C to continue reaction 2 hours. After the reaction, using NaHCO 3 adjusting pH to 6-7, then extracted with ethyl acetate (3×100 ml), the organic phase is dried with anhydrous sodium sulfate, filtered, concentrated, to obtain the title compound (4.8g, yield 95.4%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175204-80-5, its application will become more common.

Reference:
Patent; Shandong Xuan Bamboo Pharmaceutical Technology Co., Ltd.; Wu, Yong qian; (49 pag.)CN105461714; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, 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, 6318-51-0, blongs to pyridine-derivatives compound. Application In Synthesis of (4-Chlorophenyl)(pyridin-2-yl)methanone

(1) The chiral ligand L2 (17.3 mg, 0.025 mmol), metal complex [Ir(COD)Cl] 2 (8.0 g,0.012 mmol) was added to the reaction flask, methanol (1.5 mL) was added under an argon atmosphere, and the reaction was stirred at 25 C for 0.5 h to obtain a catalyst.(2) (4-Chlorophenyl)(pyridin-2-yl)methanone (52.2 g, 0.24 mol) was added to the autoclave, and the catalyst prepared in the step (1) was directly added, lithium t-butoxide (0.96 g). , 12mmol), methanol (100mL), charged with H2 (3.0MPa), reacted at 40 C for 12h, after the reaction is completed, the reaction solution is concentrated under reduced pressure to recover the organic solvent, then add appropriate amount of water, extracted with ethyl acetate, the liquid is The organic phase and the aqueous phase are dried and de-solubilized to obtain (S)-(4-chlorophenyl)(pyridin-2-yl)methanol (50.5 g,0.23 mol), yield: 96%, HPLC purity 98%, ee value 99.9%.The 1H NMR spectrum and the 13C NMR spectrum of (S)-(4-chlorophenyl)(pyridin-2-yl)methanol prepared in this example are shown in Fig. 1 and Fig. 2, respectively, from Fig. 1 and Fig. 2 The resulting (S)-(4-chlorophenyl)(pyridin-2-yl)methanol product can be determined. Racemic compound (4-chlorophenyl)(pyridin-2-yl)methanol and (S)-(4-chlorophenyl) prepared in Example 10The HPLC analysis spectra of the (pyridin-2-yl)methanol product are shown in Figures 3 and 4, respectively.Comparing Fig. 3 and Fig. 4, it can be seen that the two racemates of (4-chlorophenyl)(pyridin-2-yl)methanol have different peak times in the HPLC analysis spectrum.It was confirmed that the final preparation of Example 10 was (S)-(4-chlorophenyl)(pyridin-2-yl)methanol, and the product was highly pure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6318-51-0, its application will become more common.

Reference:
Patent; Zhejiang University of Technology; Zhong Weihui; Ling Fei; Nian Sanfei; (17 pag.)CN109879800; (2019); A;,
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. 27652-89-7, name is (4-Chlorophenyl)(pyridin-2-yl)methanol, the common compound, a new synthetic route is introduced below. COA of Formula: C12H10ClNO

To a stirred solution of (4-chlorophenyl) (pyridin-2-yl) methanol (5 g, 22.83 mmol) in CH2C12 (85 mL) under argon atmosphere was added pyridinium chlorochromate (5.9 g, 27.37 mmol, 1.2 equiv) and celite (5 g) at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 h. After completion of the reaction, the reaction mixture was filtered through celite, washed with CH2C12 and the filtrate was concentrated under reducedpressure. Purification using silica gel column chromatography (20% EtOAc Hexanes as eluent) afforded 3.5 g of (4-chlorophenyl) (pyridin-2-yl) methanone (Yield = 7 1%). ESI + MS: m/z 218 ([M + Hj).

The synthetic route of 27652-89-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BROAD INSTITUTE, INC.; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOLSON, Edward; WAGNER, Florence, Fevrier; WEIWER, Michel; SCOLNICK, Edward; PALMER, Michelle; LEWIS, Michael; PAN, Jennifer, Q.; ZHANG, Yan-Ling; XU, Qihong; (323 pag.)WO2016/100823; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, 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, Recommanded Product: 103058-87-3, blongs to pyridine-derivatives compound. Recommanded Product: 103058-87-3

Example 217A 5-cyclopropyl-2-methoxynicotinaldehyde 5-Bromo-2-methoxynicotinaldehyde (4 gg, 18.52 mmol) in 1,4-dioxane (40 mL) was degassed with nitrogen for 5 minutes, and cyclopropylboronic acid (2.39 g, 27.78 mmol), cesium fluoride (7.84 g, 51.0 mmol) and PdCl2dppf ([1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.756 g, 0.926 mmol) were added. The mixture was degassed again with nitrogen and heated to 100 C. under nitrogen for 2 hours. The mixture was cooled to room temperature and ethyl acetate (50 mL) was added. The mixture was stirred for 5 minutes, filtered over a pad of silica gel, washed with ethyl acetate/heptane (1:1), concentrated and purified via flash chromatography (0 to 20% methyl tert-butyl ether in heptane) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 10.18 (s, 1H), 8.26 (d, J=2.7 Hz, 1H), 7.67 (d, J=2.7 Hz, 1H), 3.94 (s, 3H), 1.95 (tt, J=8.4, 5.0 Hz, 1H), 0.99-0.90 (m, 2H), 0.70-0.63 (m, 2H); MS (ESI+) m/z 178 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (247 pag.)US2018/99932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1060814-91-6, 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. 1060814-91-6, name is Ethyl 2-(4-bromopyridin-2-yl)acetate, molecular formula is C9H10BrNO2, 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 ethyl 2-(4-bromo-2-pyridyl)acetate (1.20 g, 4.92 mmol) in THF (15 mL) and water (10 mL) was added LiOH (471 mg, 19.6 mmol). The mixture was stirred at 15 C for 16 hours. On completion, the reaction mixture was concentrated in vacuo to remove the THF. The residue was acidified with 1 M hydrochloric acid to adjust the pH 1H NMR (400MHz, DMSO-d6) delta = 12.56 (br. s., 1H), 8.39 (d, J = 5.2 Hz, 1H), 7.67 (d, J = 1.6 Hz, 1H), 7.57 (dd, J = 1.6, 5.2 Hz, 1H), 3.77 (s, 2H). Step 3 – Ethyl 2-[[2-(4-bromo-2-pyridyl)acetyl]amino]-2-methyl-propanoate

According to the analysis of related databases, 1060814-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 955372-86-8, 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 955372-86-8 as follows.

Step 2: Preparation of methyl 3-bromo-5-fluoroisonicotinate TMSCHN2 (180 mL, 360 mmol, 2 equiv) was added into a solution of 3-bromo-5-fluoroisonicotinic acid (40 g, 182 mmol, 1 equiv), THF (240 mL), and MeOH (80 mL) dropwise with stirring at 0 C. under nitrogen. The resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1/9) to afford the title compound (35 g, 83%) as yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,955372-86-8, its application will become more common.

Reference:
Patent; Genentech, Inc.; Terrett, Jack Alexander; Chen, Huifen; Constantineau-Forget, Lea; Larouche-Gauthier, Robin; Lepissier, Luce; Beaumier, Francis; Dery, Martin; Grand-Maitre, Chantal; Sturino, Claudio; Volgraf, Matthew; Villemure, Elisia; (138 pag.)US2019/284179; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 167884-17-5, Adding some certain compound to certain chemical reactions, such as: 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol,molecular formula is C8H8N2O, 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 167884-17-5.

(5) Imidazo[1,2-a]pyridine-5-carbaldehyde Ethyl imidazo[1,2-a]pyridine-5-carboxylate (824 mg) was dissolved in methylene chloride (40 mL). Diisobutylaluminum hydride (1 M solution in toluene) (5 mL) was added at -78C and the mixture was stirred at – 78C for two hours. Diisobutylaluminum hydride (1 M solution in toluene) (10 mL) was further added to the mixture, followed by stirring at -78C for two hours. Methanol (1 mL) was added to the reaction mixture at – 78C, followed by addition of a 20% (+)-potassium sodium tartrate solution. After stirring at room temperature, the reaction mixture was filtered through celite and washed with methylene chloride, followed by extraction with methylene chloride twice. The organic layers were combined, washed with a saturated sodium chloride solution and then dried over magnesium sulfate. The drying agent was removed by filtration and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in acetone (15 mL). 80% manganese dioxide (3 g) was added and the mixture was stirred at room temperature for 11 hours and 20 minutes. The reaction mixture was filtered and washed with acetone. The solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol) to obtain the title compound (96 mg). 1H-NMR (400 MHz, CDCl3) delta(ppm): 7.35-7.44 (m, 1H), 7.53 (d, J=6.8 Hz, 1H), 7.88 (s, 1H), 7.99 (d, J=8.8 Hz, 1H) , 9.04 (s, 1H) , 9.92 (s, 1H) .

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. 167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2017275; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol, 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, 582303-10-4, blongs to pyridine-derivatives compound. Product Details of 582303-10-4

To a mixture of methyl (4- (difluoromethyl) -6-hydroxy-l- benzothiophen-3-yl) acetate (78 mg) and THF (dry) (2 mL) were added (2, 6-dimethylpyridin-3-yl) methanol (43.2 mg) , tri-n- butylphosphine (0.212 mL) and ADDP (94 mg) at room temperature. The mixture was stirred at room temperature for 2 h. To the mixture were added ADDP (94 mg) and tri-n-butylphosphine (0.212 mL) , and the mixture was stirred at room temperature for 30 min. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by short pad of silica gel (EtOAc/hexane ) . To a mixture of the residue and THF (2 mL) was added IN NaOH (1 mL) at room temperature. The mixture was stirred at room temperature for 16 h. The mixture was neutralized with IN HCl at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgS04 and concentrated in vacuo. The crude product was purified by preparative HPLC (C18, H20/CH3CN (including 10 mM NH4HC03) ) . The fraction was extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgS0 and concentrated in vacuo. The residue was crystallized from EtOAc-hexane to give the title compound (29.1 mg) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,582303-10-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKAKURA, Nobuyuki; BANNO, Yoshihiro; TERAO, Yoshito; OCHIDA, Atsuko; MORIMOTO, Sachie; KITAMURA, Shuji; TOMATA, Yoshihide; YASUMA, Tsuneo; IKOMA, Minoru; MASUDA, Kei; WO2013/125732; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1796-84-5, 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. 1796-84-5, name is 4-Ethoxy-3-nitropyridine, molecular formula is C7H8N2O3, 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.

A solution consisting of 4-ethoxy-3-nitropyridine (15.0 g, 97.3 mmol) and EtNH2 (46.5 mL, 70% aq. solution, 584 mmol) in EtOH (30 mL) was stirred at 85 C in a pressure vessel for 2 h. Removal of all volatiles in vacuo afforded the title compound (16.2 g, 99 %). MS (ES+) m/z 168 (M+H) +.

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 1796-84-5, 4-Ethoxy-3-nitropyridine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/46678; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 97004-04-1, 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.97004-04-1, name is (6-Chloropyridin-3-yl)methanamine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

EXAMPLE 29 To a mixture of O-methyl-N-nitroisourea (1.25 g, 10.53 mmol), water (20 ml) and concentrated hydrochloric acid (0.85 ml, 10.03 mmol) was added 5-(aminomethyl)-2-chloropyridine (1.43 g, 10.03 mmol) dropwise over 5 minutes at room temperature with stirring. The reaction mixture was neutralized with 40% aqueous sodium hydroxide solution and adjusted to pH 7.2. After 17 hours of stirring at room temperature, the resulting crystals were collected. The crystals were washed with water and dried. As a result, 1.16 g (47.3% yield) of O-methyl-N-(6-chloro-3-pyridylmethyl)-N’-nitroisourea was obtained as white crystals. M.p. 112-113 C. 1 H-NMR (CDCl3) delta: 3.98 (3H, s), 4.57 (2H, d, J=6.0 Hz), 7.38 (1H, d, J=8.2 Hz), 7.63 (1H, dd, J=8.2 Hz, 2.4 Hz), 8.36 (1H, d, J=2.4 Hz), 9.43 (1H, br). IR (nujol): 3250, 1590, 1520, 1390, 1240, 1210 (cm-1).

The chemical industry reduces the impact on the environment during synthesis 97004-04-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6008363; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem