Tag: M.W=300-400

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.137736-63-1, name is 2-(4-Bromophenoxy)-5-(trifluoromethyl)pyridine, molecular formula is C12H7BrF3NO, molecular weight is 318.09, as common compound, the synthetic route is as follows.name: 2-(4-Bromophenoxy)-5-(trifluoromethyl)pyridine

(a) (E)-Ethyl 3-(l-(4-((5-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)- lH-indol-3-yl)acrylate (3) was prepared as follows: A mixture of compound 1 (Alfe Aesar, 0.5 g, 1.0 eq), compound 2, Cul (0.2 eq), K2C03 (3 eq), and dimethylglycine (Aldrich, 0.1 eq) in DMF (10 mL) was heated at 160 °C for 30 minutes under microwave. The mixture was dissolved in water/EtOAc (20 mL/100 mL). The organic layer was washed with brine, concentrated and purified by column (silica gel, EtOAc/hexane 1/10) to afford compound 3 as a white solid (0.4 g, 40percent): ?-NMR (400MHz, CDC13) ?: 8.42 (s, IH), 7.85 – 7.92 (m, 3H), 7.54 (s, IH), 7.47 – 7.51 (m, 3H), 7.23 – 7.29 (m, 4H), 7.06 (d, IH, 8.8Hz), 6.45 (d, IH, 16Hz), 4.23 (q, 2H, 7.1Hz), 1.29 (t, 3H, 7.2Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,137736-63-1, 2-(4-Bromophenoxy)-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PURDUE PHARMA L.P.; YAO, Jiangchao; WO2013/64883; (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.96428-50-1, name is Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C18H18N2O3, molecular weight is 310.35, as common compound, the synthetic route is as follows.SDS of cas: 96428-50-1

253 ml of 2 N aqueous sodium hydroxide solution were added to a solution of 15.7 g of ethyl 8-(benzyloxy)- 2-methylimidazo[1 ,2-a]pyridine-3-carboxylate (50.59 mmol) from Example 38A in 253 ml of 1 ,4-dioxane, and the mixture was stirred at RT for 14 h. 101 ml of 6 N aqueous hydrochloric acid were then added. The solid formed was filtered off, washed with water and methyl tert-butyl ether and then dried under reduced pressure at 40 C. overnight. This gave 15.49 g (108% of theory) of 8-(benzyloxy)-2- methylimidazo[1 ,2-a]pyridine-3-carboxylic acid.10698] LC-MS (Method 2): R=0.66 mm10699] MS (ESpos): mlz=283.0 (M+H)10700] ?H-NMR (400 MHz, DMSO-d5): oe=2.67 (s, 3H),5.41 (s, 2H), 7.30 (m, 1H), 7.35-7.48 (m, 4H), 7.57 (d, 2H),9.02 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96428-50-1, Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (95 pag.)US2016/347770; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 823221-95-0, 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 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-Chloro-4-iodo-2-trifluoromethyl-pyridine (7.25 g, 23.6 mmol) in DMSO (70.0 mL) were added diethylmalonate (4.53 g, 28.3 mmol) and cesium carbonate (11.52 g, 35.3 mmol). The reaction mixture was stirred at 100C for 5 h. Reaction completion was confirmed by TLC. Upon cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Crude product was purified by flash column chromatography on silica gel eluting with 10-20% ethyl acetate/hexanes to yield diethyl 2-(5-Chloro-2-trifluoromethyl-pyridin-4-yl)-malonic acid diethyl ester 1. MS ESI/APCI calc’d. for C13H13CIF3NO4[M + H]+339.7, found 340.2.

According to the analysis of related databases, 823221-95-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHAO, Pengcheng Patrick; YE, Feng; VACHAL, Petr; WO2015/94932; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 173528-92-2 ,Some common heterocyclic compound, 173528-92-2, molecular formula is C20H18N2O3S, 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.

EXAMPLE 8 (E)-4-[2-[2-[[(p-Hydroxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine In DMF was dissolved 2.00 g of the (E)-4-[2-[2-[[(p-methoxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine obtained in Example 3, followed by addition of 1.91 g of sodium methanethiolate, and the mixture was stirred at 100 C. overnight and then after-treated. The resulting crystals were recrystallized from methanol to provide 0.19 g of the title compound (white powders). m.p. 293-296 C. (decomp.) Elemental analysis for C19 H16 N2 O3 S

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. 173528-92-2, HMN-154, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Shinyaku Company, Limited; US5972976; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16727-47-2, Adding some certain compound to certain chemical reactions, such as: 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine,molecular formula is C19H16BrNO2, 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 16727-47-2.

To a stirred solution of 16-1 (5.0 g, 13.5 mmol) in Dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (5.12 g, 20.2 mmol) and KOAc (2.64 g, 27.0 mmol). The reaction mixture was degassed with argon for 10 minutes. PdCl2(dppf).DCM (1.10 g, 1.35 mmol) was added and the resulting mixture was stirred at 100 oC for 16 hours. The reaction was then cooled to room temperature and filtered through a short bed of celite. The filtrate was diluted with Ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-5% Ethyl acetate in Hexane) to afford 25-1 (3.5 g, 62%) as a pale yellow solid.

According to the analysis of related databases, 16727-47-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153747-97-8, 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 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of tert- Butyl 4-(5-bromo-2-pyridinyl)-l-piperazinecarboxylate (0.203 g, 0.593 mmol) and7V-({(55)- 3-[3-fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-l,3-oxazolidin-5- yl}methyl)acetamide (0.270 g, 0.714 mmol) in dmf (4 niL), EtOH (1.5 niL), toluene (2.5 mL) and K2CO3 (1 mL, 2 M, 2 mmol) was purged with nitrogen. PdCl2(dppf) (24 mg, 0.03 mmol) was added and the mixture was heated to 900C under nitrogen for 1 h, then partitioned between EtOAc and water. Column chromatography (EtOAc) gave the titled compound (0.21O g, 69%) as a white solid. APCI MS m/z 514 (M + H). 1H NMR (400 MHz, DMSO-J6) delta 8.32 (bs, IH), 8.27 (t, J= 5.9 Hz, IH), 7.75 (ddd, J- 8.9, 2.4, 1.7 Hz, IH), 7.53-7.60 (m, 2H), 7.38 (dd, J- 8.6, 2.2 Hz, IH), 6.94 (d, J= 8.9 Hz, IH), 4.72-4.79 (m, IH), 4.15 (t, J= 9.1 Hz, IH), 3.77 (dd, J = 9.2, 6.5 Hz, IH), 3.52-3.57 (m, 4H), 3.40-3.46 (m, 6H), 1.84 (s, 3H), 1.43 (s, 9H).

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 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; WO2009/120789; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 401892-47-5, 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 401892-47-5, name is 5-Bromo-2-chloro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-bromo-2-chloro-4-iodopyridine (20.0 g, 63.09 mmol) in DMF (200 mL), methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (16.15 mL, 126.18 mmol) and Cul (24.02 g, 126.18 mmol) were added at RT under argon atmosphere. The reaction mixture was heated to 100 C for 6 hours. The reaction mixture was diluted with water (200 mL) filtered off and washed with w-pentane (2 X 500 mL) and cold water (3 X 1000 mL). The separated organic layer dried over with sodium sulfate and concentrated under reduced pressure at 30 C to give the crude compound. That was purified by column chromatography (5% pet ether: EtO Ac) that resulted in the title compound (9.0g, 44%) as a liquid compound. TLC: 5% EtO Ac in pet ether. LCMS [M+H]+ = 261.0 g/mol.

According to the analysis of related databases, 401892-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; (316 pag.)WO2017/147701; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1138444-17-3 ,Some common heterocyclic compound, 1138444-17-3, molecular formula is C5H2BrClIN, 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-Bromo-2-chloro-3-iodopyridine (1.50 g, 4.71 mmol) was dissolved in THF (15 mL) and cooled to -78 C, followed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol). The mixture was stirred at -78C for 1 h. 2- (benzyloxy)acetaldehyde (0.849 g, 5.65 mmol) was added and the resulting mixture warmed to 0C and stirred for 2 h. The mixture was treated with saturated NH4C1 and extracted with ethylacetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to gave 2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol (1.54g, yield: 95%). MS (M+H): 344.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1138444-17-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); 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. 74936-72-4, name is 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

(1) Preparation of (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl) -1,4-dihydropyridine-3-carboxylic acid (700g, 2.1mol) in methanol (14 L) was added Quinidine (617g, 1.90mol). The mixture was placed at 90C under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for half an hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6 %.

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, 74936-72-4, 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-96-5, 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 1221171-96-5 as follows.

4-Amino-2-chloro-6-trifluoromethoxypyridine (45); At -78 0C, butyllithium (1.56 M in hexane, 2.2 mL, 3.4 mmol, 1.1 eq) was added dropwise to a solution of 2-chloro-4-iodo-6-trifluoromethoxypyridine (42, 1.0 g, 3.1 mmol) in THF (8 mL) followed after 10 min by benzenesulfonyl azide (0.6 g, 3.4 mmol, 1.1 eq). The reaction mixture was was allowed to reach 25 0C before being treated with a saturated aqueous solution of ammonium chloride (10 mL) and extracted with diethylehter (3 x 8 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford a crude red oil of 4-azido-2-chloro-6- trifluoromethoxypyridine. It was then dissolved in anhydrous diethylether (25 mL) and added dropwise to a suspension of lithium aluminium hydride (130 mg, 3.4 mmol, 1.1 eq) in diehtylether (25 mL). The reaction mixture was heated under reflux for 5 h before being treated with water (10 mL) and extracted with diethylether (3 x 10 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude product was purified by chromatography on silica gel using ethyl acetate/cyclohexane (1:9) as eluent which afforded pure 4-amino-2-chloro-6- trifluoromethoxypyridine (45, 0.3 g, 1.4 mmol, 46%) as a yellow oil.1H NMR (CDCl3, 300 MHz): delta = 6.41 (d, J = 1.6 Hz, 1 H), 6.07 (d, J = 1.6 Hz, 1 H),4.30 (bs, 2 H). – 19F NMR (CDCl3, 282 MHz): delta = -56.8 – 13C NMR (CDCl3, 75 MHz): delta = 157.4, 156.7, 149.7, 119.9 (q, J = 260 Hz), 107.6, 96.0. – C6H4ClF3N2O (212): calcd. (%) C 33.90, H 1.90, N 13.18; found C 33.56, H 2.01, N 12.87.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221171-96-5, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem