Month: April 2022

Application of 175204-80-5 , The common heterocyclic compound, 175204-80-5, name is 3-Amino-4-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, 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.

Preparation III; 4-(Trifluoromethyl)-3-pyridinol; A solution of 2 g (12.34 mmol) of 3-amino-4-(trifluoromethyl)pyridine in 28 ml of 50% sulfuric acid is cooled to -5 C. and a solution of 1.03 g (14.8 mmol) of sodium nitrite in 10 ml of water is added slowly. The mixture is left to return to room temperature and stirring is continued for 30 min. 25 ml of concentrated sulfuric acid are then added and the reaction mixture is stirred at 100-110 C. for 2 hours. After cooling, the reaction medium is neutralized by adding saturated sodium bicarbonate solution to pH 6-7, and the mixture is extracted with ethyl acetate. The organic phase obtained is washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 1.92 g of the expected compound in the form of a brown powder (yield=95%). M.p.=112-114 C.

The synthetic route of 175204-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratoires Fournier S.A.; US2007/54955; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, 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 tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, blongs to pyridine-derivatives compound. Safety of tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

[00316] fer -Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0. 3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2S03 (1.5 eq) was added via addition funnel. After completion of Na2S03 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2C03 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3- methylpyridine-1 -oxide (95%) that was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SWINNEY, Kelly, Ann; HURTER, Patricia, Nell; NADIG, David, E.; SMITH, David; THOMAS, Vance, Hayden; WARMAN, Martin, Paul; WO2015/73231; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 106047-28-3, 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 106047-28-3 as follows.

Step 2 1-methyl-4-nitro-2-[2-(3-pyridyl)pyridin-6-ylamino]benzene This compound was prepared by version of the method described in the document (J. Org. Chem., 2000, 65, 1144-1157.). To 940 mg of 2-bromo-6-(3-pyridyl)pyridine obtained in the step 1, 730 mg of 2-methyl-5-nitroaniline, 37 mg of tris(dibenzylideneacetone)dipalladium (0), 75 mg of (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(+-)-BINAP] and 1.82 mg of cesium carbonate, 12 ml of toluene was added and the mixture was stirred with heating at 110C for 24 hours under an argon atmosphere. After air cooling, the reaction solution was diluted with ethyl acetate and insolubles were removed by filtration. The solvent in the filtrate was distilled off under reduced pressure and the residue was crystallized by adding diethyl ether. The resulting crystal was collected by filtration and then washed with ethyl acetate-diethyl ether to obtain 646 mg of the objective compound as a yellow crystal. Melting point: 148-150C 1H-NMR(CDCl3)delta: 2.42(3H, s), 6.53(1H, br), 6.80(1H, d), 7.35(2H, d), 7.44(1H, dd), 7.69(1H, m), 7.83(1H, dd), 8.44(1H, dt), 8.65(1H, dd), 9.09(1H, d), 9.20(1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,106047-28-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1533304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 898746-42-4 , The common heterocyclic compound, 898746-42-4, name is 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5FN2, 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.

6-Fluoro-1H-pyrrolo[2,3-b]pyridine (2.50 g, 18.36 mmol)Soluble in DMF (50mL),Cool to 0 C,Then add bromine to it(3.20g, 20.00mmol)DMF (20 mL) solution,After the dropwise addition was completed, the resulting reaction solution was stirred at room temperature for 2 hours.Then water (100 mL) was added and a large amount of solid precipitated.Filter under reduced pressure, and the filter cake was washed with water (30 mL×2).Then dried under vacuum at 60 C for 24 hours.The title compound was obtained as a white solid (3.44 g, 87%).

The synthetic route of 898746-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; Nie Biao; Xu Juan; Yan Huan; Chen Jianping; (90 pag.)CN108727369; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 107867-51-6 ,Some common heterocyclic compound, 107867-51-6, molecular formula is C6H6F3N3, 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.

A solution of Intermediate 18 (150 mg, 0.436 mmol) in DMSO (8.0 ml) was treated with 5-(trifluoromethyI)pyridine-2,3-diamine (85 mg, 0.479 mmol) and the mixture stirred at 70C for 2 h. After cooling to room temperature the reaction was quenched with water to afford a precepitate. The precepitate was filtered off and washed with water. The filtered solid was dissolved in EtOAc and washed with NaHC03, brine, and dried (MgS04) and concentrated. Trituration of the solid from ether / hexane followed by filtration afforded 143 mg of Methyl 2-(Cis-3-(5-(3-fluoro-4-(6-(trifluoromethyl)-3H-imidazo[4,5-)]pyridin-2-yl)phenyl)pyrimidin-2-yloxy)cyclobutyl)acetate as a tan solid. LC-MS (M+l)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,107867-51-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; BALKOVEC, James, M.; KRIKORIAN, Arto, D.; MILLER, Daniel, J.; GUIADEEN, Deodial; YANG, Ginger Xu-Qiang; JIAN, Tianying; WU, Zhicai; YU, Yang; NARGUND, Ravi, P.; VACHAL, Petr; HE, Shuwen; LAI, Zhong; HONG, Qingmei; DEVITA, Robert, J.; KIM, David; TING, Pauline, C.; WO2013/74387; (2013); 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.185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.name: 3-Bromo-2-chloro-6-picoline

In 21 mL of carbon tetrachloride, 3-bromo-2-chloro-6-methylpyridine (880 mg, 4.26 mmol) was dissolved, and N-bromosuccinimide (682 mg, 3.83 mmol) and AIBN (70 mg, 0.426 mmol) were added, followed by stirring at 90C for one hour. The resulting reaction solution was concentrated, and the residue thus obtained was purified by silica gel column chromatography (chloroform/methanol = 100/0 to 95/5), whereby 3-bromo-6-(bromomethyl)-2-chloropyridine was obtained as a crude purified product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,185017-72-5, 3-Bromo-2-chloro-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SUGIMOTO, Tetsuya; TAKAHASHI, Hidekazu; MITSUYA, Morihiro; MASUKO, Norio; SOOTOME, Hiroshi; EP2821406; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3678-62-4 ,Some common heterocyclic compound, 3678-62-4, molecular formula is C6H6ClN, 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.

1Og of 2-chloro-4-methylpyridine are dissolved in 50 ml of CH3CN and heated to- 85C. Then a mixture of 32g N-Chlorosuccinimid and l,6g AIBN is added over a period of 5 minutes. The. resulting, mixture is refluxed for two hours, then the solvent is removed in vacuo, the residue treated with 100ml of CH2Cl2 and washed with water 2 times. The organic phases are collected, dried over Na2S04 and the residue obtained after evaporation of the solvent is distilled (80C, 100 mTorr). Yield 79%

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. 3678-62-4, 2-Chloro-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10643; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-01-8, 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. 17282-01-8, name is 3-Bromo-2-fluoro-5-picoline. A new synthetic method of this compound is introduced below.

To a solution of B9.1 (300 mg, 1.596 mmol) in THF(10 mL) at -78 oC was added LDA (2 M, 0.8 mL) and the mixture was stirred at -78 oC for 2 h. The mixture was quenched by10 mL H2O and extracted with EtOAc (10 mL x 3). The combined organic phase was concentrated to give the crude product, which was purified by flash chromatography (Normal phase, silica gel, PE_EtOAc=0-100%, UV254 & UV280) to give the title compound (130 mg , 43%) as a yellow oil. 1H-NMR (400 MHz, CDCl3) delta ppm 2.37 (s, 3H), 7.19 (d, 1H), 8.05 (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,17282-01-8, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue; ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (193 pag.)WO2017/221092; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 171919-37-2 , The common heterocyclic compound, 171919-37-2, name is 1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, molecular formula is C9H8N2O2, 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 suspension of 1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (10.0 g, 56.8 mmol), prepared as described above in Alternative A or B, in anhydrous DCM (390 mL) cooled on ice, oxalyl chloride (14.4 mL, 170.4 mmol) was added dropwise over 15 mm and the mixture was stirred at room temperature for 2 h. The mixture was then concentrated in vacuo to give a yellow solid, which was treated with tert-butanol (300 mL, 3.14 mol), followed by an addition of potassium tert-butoxide (10.2 g, 91 mmol). The resulting mixture was stirred at room temperature for 16 h and then concentrated in vacuo. The crude was purified by flash column chromatography (Silica 120 g, 0-10% MeOH in DCM) to give the product (12.6 g, 86%) as a light brown solid. UPLC-MS (Acidic Method, 2 mm): rt 1.10 mm, m/z 233.1 [M+H]. ?HNIVIR (400 MHz, DMSO-d6) ppm 8.35 (dd, J= 4.6, 1.6 Hz, 1H), 8.27 (dd, J= 7.8, 1.6 Hz, 1H), 8.20 (s, 1H), 7.27 (dd, J= 7.9, 4.6 Hz, 1H), 3.86 (s, 3H), 1.56 (s, 9H).

The synthetic route of 171919-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; KINCAID, John; DUNCTON, Matthew; (142 pag.)WO2018/213810; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53174-98-4, 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 53174-98-4, name is Thieno[2,3-b]pyridine-2-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Example 161 N-(4-{trans-2-[(thieno[2,3-b]pyridin-2-ylmethyl)amino]cyclopropyl}phenyl)-3-(trifluoromethyl)benzamide hydrochloride By a method similar to Example 65, the title compound (10 mg) was obtained from N-[4-(trans-2-aminocyclopropyl)phenyl]-3-(trifluoromethyl)benzamide hydrochloride (75 mg) and thieno[2,3-b]pyridine-2-carbaldehyde (44.6 mg). MS (API+): [M+H]+ 468.0. 1H NMR (300 MHz, CD3OD) delta 1.36-1.57 (2H, m), 2.41 (1H, ddd, J = 10.2, 6.5, 3.7 Hz), 3.01 (1H, dt, J = 7.6, 4.0 Hz), 4.73 (2H, s), 7.07 (2H, d, J = 8.7 Hz), 7.44-7.54 (2H, m), 7.61 (2H, d, J = 8.7 Hz), 7.70-7.79 (1H, m), 7.90 (1H, d, J = 7.9 Hz), 8.15-8.30 (3H, m), 8.58 (1H, dd, J = 4.7, 1.5 Hz).

According to the analysis of related databases, 53174-98-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TOMITA, Naoki; KAJII, Shigeo; CARY, Douglas Robert; TOMITA, Daisuke; IMAMURA, Shinichi; TSUCHIDA, Ken; MATSUDA, Satoru; HARA, Ryujiro; EP2743256; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem