Day: September 23, 2021

Adding a certain compound to certain chemical reactions, such as: 1214334-70-9, 5-Bromo-6-methoxypicolinic 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, Computed Properties of C7H6BrNO3, blongs to pyridine-derivatives compound. Computed Properties of C7H6BrNO3

A solution of 5-bromo-6-methoxypicolinic acid (1.08 g, 4.45 mmol, 1.05 equiv.) in DCM (40.0 mL) at ambient temperature was treated with a catalytic amount of DMF (4 drops) and oxalyl chloride (1.17 mL, 13.4 mmol, 3.0 equiv.). The resultant mixture was stirred at ambient temperature for 1 h at which point LCMS monitoring showed completion of the reaction. The mixture was concentrated, diluted with anhydrous THF (20.0 mL), concentrated again and dried under high vacuum for 1 hour. The residue was diluted in anhydrous THF (20.0 ml), treated with triethylamine (1.86 mL, 13.4 mmol, 3.0 equiv.) and cooled to 0 C. A solution of (R)-2-(benzofuran-2-yl)-2-(4- methoxybenzylamino)ethanol (1.32 g, 4.45 mmol, 1.0 equiv.) in THF (20.0 ml) was quickly added and the resultant mixture was stirred at 0 C for 30 minutes. A saturated aqueous solution of NaHCO3 and EtOAc were then successively added. The layers were separated,and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography on silica (0-40% EtOAc / hexanes) to afford amide as white foam (1.78 g, 78%). LCMS (ES+) [M+Hj+: 511.2/513.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17282-40-5, 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 17282-40-5 as follows.

General procedure: Mixture of ethyl acetoacetate(1, 211 mg, 0.153 mmol), hydrazine (2, 81 mg, 0.153), 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde (4a, 406 mg,0.153 mmol), 1-(2-ethoxy-2-oxoethyl)pyridinium ylide (4, 272mg, 0.153 mmol), 0.1 equivalents of trimethylamine (16 mg,0.015 mmol) in15 mL EtOH were refluxed in a pre-heated oilbath (80 C) under the blanket of nitrogen for 30 min till the completion of reaction (TLC, 20 % dicholromethane in hexanes; Rf = 0.3). The reaction mixture was diluted with dichloromethane (10 mL) and the organic solution was washed with water (20 mL) and brine (20 mL) and dried over anhydrousNa2SO4. Column chromatographic purification on silica gelwith increasing amount of dichlormethane in hexanes provided 8a as a free flowing solid in about 88 % yield. Analytical samples were obtained through from the recrystallization in EtOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-40-5, its application will become more common.

Reference:
Article; Tangeti, Venkata Swamy; Vasundhara; Satyanarayana; Pavan Kumar, Kaja Srinivas; Asian Journal of Chemistry; vol. 29; 7; (2017); p. 1525 – 1532;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1427-06-1, name is Methyl 6-fluoropyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 6-fluoropyridine-3-carboxylate

( (2S) -5- (4- (trifluoromethyl) phenyl) piperidin-2-yl) methanol (294 mg, 1.13 mmol) , methyl 6-fluoropyridine-3-carboxylate (198 mg, 1.28 mmol) and K 2CO 3 (489 mg, 3.54 mmol) were dissolved in DMSO (3 mL) . The mixture was stirred for 24 h at an oil-bath temperature of 50 . The reaction mixture was cooled to room temperature, and to the mixture was added saturated NaCl solution (50 mL) , and the mixture was extracted with EtOAc (40 mL×2) . The combined organic layers were dried over anhydrous Na 2SO 4, and concentrated in vacuo to give a crude product, which was purified by silica-gel column chromatography (eluent: PET/EtOAc (v/v) = 5: 1) to give colorless oil (166 mg, 37%) . [2165] MS (ESI, pos. ion) m/z = 395.3 [M+1] +.

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, 1427-06-1, Methyl 6-fluoropyridine-3-carboxylate.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHONG, Xue; WANG, Feng; LI, Xuke; HE, Wei; PAN, Wei; HUANG, Jiuzhong; ZHANG, Yingjun; ZHENG, Changchun; (0 pag.)WO2020/11147; (2020); 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Quality Control of 5-Methylpyridin-2(1H)-one

General procedure: The coupling reaction was performed as follows: in a typical process, 5-methyl-2-(1H)-pyridone(1 mmol), aryl halide (1 mmol), base (2 mmol) and solvent (5 mL) were added to an oven-dried tube containing 5% (based on copper) MOF catalyst or copper salt. The mixture was stirred at desired temperature for 2 h. After being cooled to room temperature, the catalyst was filtrated and washed with ethyl acetate. The products were isolated by a series 1500 preparative high performance liquid chromatography system (SSI, Charlotte, NC, USA) equipped with a UV-VIS detector, using a Kromasil C18 column (50 x 250 mm) and gradient elution with a H2O (A)-acetonitrile (B) the mobile phase. The gradient program was 0 min, 10% B; 20 min, 35% B. The flow rate of mobile phase was 40 mL/min, and the detection wavelength was 220 nm. Fractions were collected and evaporated to afford the pure products.

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Article; Long, Wei; Qiu, Wenge; Guo, Chongwei; Li, Chuanqiang; Song, Liyun; Bai, Guangmei; Zhang, Guizhen; He, Hong; Kuznetsov, Maxim L.; Molecules; vol. 20; 12; (2015); p. 21178 – 21192;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56187-37-2, 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. 56187-37-2, name is 2-(3,5-Dichloro-4-oxopyridin-1(4H)-yl)acetic acid. A new synthetic method of this compound is introduced below.

In a dry reaction flask, 137.66 g of 3,5-dichloro-4-pyridone-1-acetic acid (0.62 mol) and 222.64 gDibenzothiazyl disulfide (DM, 0.6696 mol) was dissolved in 500 mL of dichloromethane and 54 g (0.682 mol) of pyridine was added.The reaction was stirred at room temperature for 1 hour, and then an aqueous solution of triethyl phosphite (118.47 g of triethyl phosphite dissolved in 150 mL of methylene chloride, 0.713 mol) was added dropwise slowly.1-2 hours dropwise addition is complete, the reaction temperature was controlled at 20-25 C for 1-2 hours, filtered and the filtrate cooled down to below 10 C,Crystals were precipitated, suction filtered and dried to give 234.8 g of cefoxitin side chain acid active ester (0.6063 mol). The yield was 97.1% and the HPLC purity was 99.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56187-37-2, 2-(3,5-Dichloro-4-oxopyridin-1(4H)-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Co., Ltd.; Wang Jun; Zuo Cuiyong; Gao Feifei; (10 pag.)CN105017286; (2017); B;,
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. 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoropyridine-5-carbaldehyde

Intermediate 8.2- ^S-formylpyridm-2-ylV3-azaspi- |’5.51undecan-9-yl)aSodium bicarbonate (2.70 g, 5 equiv), 2-fluoropyridine-6-carboxaldehyde (0.80 g, 1 equiv) and the hydrochloride salt of 3-azaspiro[5.5]undec-9-ylacetic acid (1.59 g, 1 equiv) were stirred at 80 C in NMP (12 mL) for 5 hours. The mixture was cooled to room temperature, acidified with 1 M HCl (25 mL, 4 equiv), diluted with water, and extracted with dichloromethane. The combined organic layers were concentrated in vacuo and purified by silica gel chromatography (0% acetone:dichloromethane to 50% acetoneidichloromethane) to give the pure aldehyde as a white solid: [ H]+ m/z 317.

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, 677728-92-6, 2-Fluoropyridine-5-carbaldehyde.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CERNAK, Timothy, A.; BALKOVEC, James, M.; NARGUND, Ravi, P.; REITER, Maud; SPERBECK, Donald, M.; DYKSTRA, Kevin, D.; YU, Yang; DREHER, Spencer; MALONEY, Kevin, M.; WU, Zhicai; DEVITA, Robert, J.; VERRAS, Andreas; WO2012/9217; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, Adding some certain compound to certain chemical reactions, such as: 13466-38-1, name is 5-Bromopyridin-2-ol,molecular formula is C5H4BrNO, 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 13466-38-1.

(i) 5-bromo-l-ethylpyridin-2(lH)-onePotassium tert-butoxide (328 mg) was added to 5-bromopyridin-2(lH)-one (509 mg) in dimethoxyethane (15 mL) at 20C under an atmosphere of nitrogen and stirred for 30 min. Potassium carbonate (283 mg) and iodoethane (0.236 mL) were added to the reaction mixture and the resulting suspension was stirred at 95C for 3 h. The reaction mixture was cooled and filtered, evaporated to dryness and redissolved in dichloromethane, and washed with 0.1M hydrochloric acid. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford an oil which was purified by chromatography on silica eluting with 30 to 50% ethyl acetate in z’sohexane. Pure fractions were evaporated to dryness to afford the subtitled compound (367 mg).1H NMR (500 MHz, DMSO) delta 8.04 (d, IH), 7.50 (dt, IH), 6.35 (d, IH), 3.88 (q, 2H), 1.19 (t, 3H). m/e (APCI+) 204 [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. 13466-38-1, 5-Bromopyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; KINCHIN, Elizabeth; MATHER, Andrew; METE, Antonio; MILLICHIP, Ian; STANIER, Andrew Geoffrey; WO2011/154677; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17874-79-2 ,Some common heterocyclic compound, 17874-79-2, molecular formula is C8H7NO4, 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.

5-(methoxycarbonyl)pyridine-2-carboxylic acid (100 mg, 0.55 mmol) was dissolved in acetonitrile (1 mL). Triethylamine (0.230 mL, 1.66 mmol) and O-benzotriazol-1-yl- tetramethyluronium hexafluorophosphate (314 mg, 0.83 mmol) were added. The reaction mixture was stirred at rt for 5 min. 3,3,3-trifiuoropropylamine hydrochloride (83 mg, 0.55 mmol) was added and the reaction mixture was stirred at ambient temperature for 2h. The solvent was removed in vacuo and the crude was partioned between ethyl acetate and IM sodium hydroxide. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude was purified by column chromatography using a gradient of ethyl acetate in heptane yieded 38 mg (25%) of the title compound as a white solid; 1H NMR (400 MHz, DMSOtZ6) delta ppm 9.17 (t, 1 H), 9.11 (d, 1 H), 8.48 (dd, 1 H), 8.18 (d, 1 H), 3.92 (s, 3 H), 3.53 – 3.60 (m, 2 H), 2.54 – 2.66 (m, 2 H); MS (ESI) m/z 277 [M+H+], m/z 275 [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. 17874-79-2, 5-(Methoxycarbonyl)picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/130320; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 13362-28-2, name is 2-Amino-4-pyridinecarboxylic acid, molecular formula is C6H6N2O2, 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. Quality Control of 2-Amino-4-pyridinecarboxylic acid

Methanol solution (1.8L) of 2-aminoisonicotinic acid (207g, 1.5mol) was added to thionyl chloride (238g, 2mol) at 50C by dropping. The solution was stirred for 5 more hours at the same temperature. Then, the solvent was removed under reduced pressure, and saturated aqueous solution of sodium carbonate was added to the residue to be basic of pH=9-10. After extracting the mixed solution by using dichloromethane (3*300ml), organic layer was collected and dried by using anhydrous sodium sulfate. The solvent was concentrated to obtain methyl 2-aminoisonicotinate (189g, 83%) (Compound 2) of yellow solid. [0518] 1H-NMR (d6-DMSO, 300MHz): delta3.96 (S, 3H) ; 7.14 (d, 1H); 7.49(br, 1H); 8.07(d, 1H); 8.18 (br, 2H, NH).

With the rapid development of chemical substances, we look forward to future research findings about 13362-28-2.

Reference:
Patent; Shin Nippon Biomedical Laboratories, Ltd.; SUZUKI, Nobuyuki; YAMASHITA, Hidetoshi; (156 pag.)EP3018125; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1190862-72-6, Adding some certain compound to certain chemical reactions, such as: 1190862-72-6, name is 5-Bromo-6-methylnicotinic acid,molecular formula is C7H6BrNO2, 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 1190862-72-6.

5-Bromo-6-methyl – nicotinic acid (0.20 g, 0.93 mmol) and 4-(4-methyl – piperazinyl small-ylmethyl) -3-trifluoromethyl – phenylamine (0.23g, 0.85 mmol ) was dissolved in N, N- dimethylformamide (10 mL), were addedunder ice-cooling 2 – (; 7-aza-benzotriazole) -Nu, Nu, Nu ‘, Nu’- tetramethylhexafluorophosphate (0.39 g, 1.02 mmol) and diisopropylethylamine (0.20 mL,1.27 mmol), and stirring was continued overnight. The reaction mixture waspoured into water, extracted with ethyl acetate, the organic phaserespectively, 5% dilute hydrochloric acid, saturated sodium bicarbonatesolution, washed with water and saturated brine, dried over anhydrous sodiumsulfate, and concentrated under reduced pressure, silica gel columnchromatography to give 5-bromo-6-methyl -N- [4- (4- methyl -piperazin-1-ylmethyl) -3-trifluoromethyl – phenyl] – nicotinamide (yellowsolid, 0.26 g ), yield 65%.

According to the analysis of related databases, 1190862-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Pharmaceuticals Holding Co.,Ltd .; WAN, HUIXIN; LI, CHUNLI; SHI, Chen; Liu, Haiyan; Li, Ping; XIA, Guangxin; HAN, Yanan; (52 pag.)CN103420977; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem