Day: April 18, 2022

Reference of 1346148-32-0 ,Some common heterocyclic compound, 1346148-32-0, molecular formula is C8H8FNO2, 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.

b) 5-Fluoro-3-methyl-pyridine-2-carboxylic acid To a solution of 5-fluoro-3-methyl-pyridine-2-carboxylic acid methyl ester (1.28 g) in MeOH (6 ml) was added at 22 C. a solution of lithium hydroxide mono hydrate (636 mg) in water (3 ml) and stiring was continued for 16 h. The mixture was diluted with water, the MeOH was evaporated at reduced pressure and the pH was adjusted to 1 using 1 N aqueous HCl. The aqueous layer was extracted with AcOEt, the organic layer was dried, evaporated and the residue was crystallized from AcOEt/n-heptane to give the title compound (1.02 g) as a pale yellow solid. MS: m/z=153.7 [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. 1346148-32-0, Methyl 5-fluoro-3-methylpicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banner, David; Guba, Wolfgang; Hilpert, Hans; Humm, Roland; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Rogers-Evans, Mark; Rombach, Didier; Woltering, Thomas; Wostl, Wolfgang; US2011/312937; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54232-43-8, 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. 54232-43-8, name is 6-Bromo-5-methoxypicolinic acid, molecular formula is C7H6BrNO3, 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 mixture of 6-bromo-5-methoxy-pyridine-2-carboxylic acid (0.3 g, 1 mmol), 3- chlorophenylboronic acid (CAN 63503-60-6, 0.23 g, 1 mmol), tris(dibenzylideneacetone)- dipalladium(0) (CAN 52409-22-0, 0.12 g), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (CAN 161265-03-8, 0.15 g) and potassium carbonate (0.21 g, 2 mmol) in 1,4-dioxane (10 mL) was stirred for 12 h at 110C under a nitrogen atmosphere. The reaction mixture was filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 10 g, eluting with 10% methanol in methylene chloride) to give the title compound (0.1 g, 29%); MS (EI): m/e = 264.0[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 54232-43-8, 6-Bromo-5-methoxypicolinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); 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.131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, molecular weight is 175.108, as common compound, the synthetic route is as follows.Recommanded Product: 131747-62-1

General procedure: A solution of lithium hydroxide (0.8 mg, 0.03 mmol) and 2′-methoxyacetophenone (26 mg, 0.157 mmol) in absolute methanol (1.5 mL) was stirred at room temperature for 15 min. To the resulting mixture was added a solution of 2-(trifluoromethyl)-3-pyridinecarboxaldehyde (6a, 28 mg, 0.16 mmol) in absolute methanol (15 mL). The reaction was stirred overnight at room temperature (approx. 18 h). The reaction was then concentrated on a rotary evaporator and the resulting oily residue purified by chromatography on silica gel using a gradient of 0-100% ethyl acetate in hexane to provide the desired product (17 mg, 35%) as a light yellow waxy solid. Prepared using the general method from lithium hydroxide (1.2 mg, 0.01 mmol), 2′-methoxyacetophenone (72 mg, 0.48 mmol) and 3-trifluoromethyl-2-pyridinecarboxaldehyde (6d, 85 mg, 0.49 mmol) in absolute methanol (final reaction volume = 4 mL). The reaction mixture was purified by chromatography on silica gel (gradient of 0-100% ethyl acetate in hexane) to give the desired product as a yellow oil that hardened upon standing (77 mg, 54%). 1H NMR (CDCl3) delta 8.82 (d, J = 4.3 Hz 1H), 8.12 (d, J = 15.0 Hz, 1H), 8.01 (dd, J = 8.0, 1.6 Hz, 1H), 7.93 (dd, J = 15.0, 1.9 Hz, 1H), 7.70 (dd, J = 7.6, 1.8 Hz, 1H), 7.51 (t, J = 7.4 Hz, 1H), 7.41 (dd, J = 7.5, 4.6 Hz, 1H), 7.07 (t, J = 7.5 Hz, 1H), 7.02 (d, J = 8.1 Hz, 1H), 3.93 (s, 3H). 13C NMR (CDCl3) delta 192.4, 158.6, 152.3, 151.6, 135.4, 134.1, 133.9, 133.5, 130.6, 128.8, 125.8, 125.1, 123.2, 120.8, 111.6, 55.7. HRMS (FAB): calcd C16H12F3NO2 + H = 308.0898, found 308.0897.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131747-62-1, 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Lounsbury, Nicole; Mateo, George; Jones, Brielle; Papaiahgari, Srinivas; Thimmulappa, Rajash K.; Teijaro, Christiana; Gordon, John; Korzekwa, Kenneth; Ye, Min; Allaway, Graham; Abou-Gharbia, Magid; Biswal, Shyam; Childers, Wayne; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5352 – 5359;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060814-36-9 ,Some common heterocyclic compound, 1060814-36-9, molecular formula is C15H21NO5, 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.

Step C: Ethyl 4,5,6,7-tetrahydrofuro[3,2-c]pyridine-2-carboxylateTo a solution of 5-tert-Butyl 2-ethyl 6,7-dihydrofuro[3,2-c]pyridine-2,5(4H)- dicarboxylate (0.5g, 1.7 mmol) in DCM was added trifluoroacetic acid (TFA) (0.13 mL, 1.7 mmol) at 0-5 C. After the completion of addition, the reaction mixture was allowed to stir for 6 hours. The excess solvent and reagents were evaporated under reduced pressure. The crude product was triturated with hexane to afford the title compound as TFA salt (0.5 g, Yield 95 %). 1H NMR (DMSO-d6) 5(ppm): 1.36 (3Eta, t, – CH3), 2.77 (2H, brs, -CH2), 3.74 (2H, brs, -CH2), 4.32-4.38 (4H, m, -CH2), 5.02 (1H, brs, -NH), 7.02 (1H, s, Ar-H); MS m/z: 196.1 (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,1060814-36-9, its application will become more common.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LTD; RAJAGOPAL, Sridharan; KILAMBI, Narasimhan; KACHHADIA, Virendra; RATHINASAMY, Suresh; BALASUBRAMANIAN, Gopalan; MANI, Umamaheswari; RAJAGOPALAN, Nirmala; PUSHPARAJ, Judy Auxcilia; ROY, Anshu Mittal; VISHWAKARMA, Lolaknath Santosh; NARAYANAN, Shridhar; KALIYAMOORTHY, Vadivel; THANASEKARAN, Ponpandian; THATAVARTHY KRISHNA, Rama; KANNAN, Kalaivani; KULATHINGAL, Jayanarayan; MOOKKAN, Jeyamurugan; CHIDAMBARAM VENKATESWARAN, Srinivasan; AHAMED ALI, Fakrudeen; WO2012/117421; (2012); 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. 17117-13-4, name is 2-Bromo-4-ethoxypyridine. A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

Under an argon atmosphere, 0.81 g (4.00 mmol) of 2-bromo-4-ethoxy-pyridine, 1.02 g (6.40 mmol) of 2,6-difluoro-pyridyl-3-boronic acid, 0.0374 g (0.032 mmol) of Pd(PPh3)4 were dissolved in 30 mL of dioxane, followed by addition of 10 mL of an aqueous solution of 5wt% K2CO3, heated to reflux, stirred for 18 h. After naturally cooled to room temperature, an appropriate amount of distilled water was added, and the solution was extracted several times with ethyl acetate, the organic phase were combined and dried over anhydrous MgSO4. After filtration, solvent was removed from the filtrate under reduced pressure to give the crude product. The crude product was purified to silica gel column chromatography using a mixture of ethyl acetate and n-hexane (v/v=1:4) as eluent to obtain 0.56g of a colorless solid product in 59.6% yield. 1H NMR (400 MHz, CDCl3, ppm): delta 8.92 (d, 1H), 8.65 (d, 1H), 7.75 (d, 1H), 7.43 d, 1H), 6.92 (s, 1H), 4.12 (m, 2H), 1.90 (m, 3H).

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, 17117-13-4, 2-Bromo-4-ethoxypyridine.

Reference:
Patent; Ocean’s King Lighting Science & Technology Co., Ltd.; ZHOU, Mingjie; WANG, Ping; ZHANG, Juanjuan; ZHANG, Zhenhua; EP2727928; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2 ,Some common heterocyclic compound, 64951-08-2, molecular formula is C8H6N2O2, 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 mixture of l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.14 mmol, HC1 salt), imidazo[l,2-a]pyridine-2- carboxylic acid (34 mg, 0.21 mmol) and EDCI.HC1 (41 mg, 0.21 mmol) in pyridine (2 mL) was stirred at 50 C for 2 h. The reaction mixture turned into white suspension from yellow solution. LCMS (Rt = 0.750 min; MS Calcd: 531.2; MS Found: 532.1 [M+H]+). The reaction mixture was diluted with water (25 mL), and then extracted with EtOAc/THF (25 mL x3, 1/1). The combined organic layer was washed with saturated aqueous NaHCCh (25 mL), brine (25 mL), dried over anhydrous Na2S04 and concentrated. The residue was triturated with MeCN (10 mL), then further purified by prep-HPLC (0.225% FA as an additive). Most of the MeCN was removed under reduced pressure and the remaining part was lyophilized to give N-(5-((5- methyl-8-(2-oxopyrrolidin-l-yl)-5H-chromeno[4,3-c]pyridin-3-yl)amino)pyridin-3- yl)imidazo[l,2-a]pyridine-2-carboxamide (29.8 mg, yield: 40%) as ayellow solid. (1680) NMR (400 MHz, DMSO-rie) d 1.56 (3H, d, J= 6.5 Hz), 2.01-2.11 (2H, m), 2.52-2.54 (2H, m), 3.85 (2H, t, J= 7.9 Hz), 5.29 (1H, q, J= 6.4 Hz), 6.79 (1H, s), 7.05 (1H, td, J= 6.8, 1.1 Hz), 7.33 (1H, dd, J= 8.7, 2.1 Hz), 7.39-7.44 (2H, m), 7.69 (1H, dd, J= 9.2, 0.9 Hz), 7.90 (1H, d, J= 8.8 Hz), 8.58 (1H, s), 8.59 (1H, t, J= 2.3 Hz), 8.65 (1H, td, J= 6.8, 1.1 Hz), 8.69 (1H, d, J= 2.3 Hz), 8.70 (1H, s), 8.78 (1H, t, J= 2.3 Hz), 9.52 (1H, brs), 10.51 (1H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Aminopyridine-2-carboxamide

[1160] 50 mg (0.121 mmol) of 2-[4-(5-chloro-2-cyano- phenyl)-5-methoxy-2-oxopyridin-1 (2H)-yl] -3 -(5-methyl-i, 2,4-oxadiazol-3-yl)propanoic acid (racemate) and 25 mg(0.181 mmol, 1.5 eq.) of 5-aminopyridine-2-carboxamide were initially charged in 1.0 ml of pyridine, 114 jtl (0.4 82 mmol, 50% in ethyl acetate, 4.0 eq.) of T3P were added and the mixture was stirred at 500 C. for 1.5 h. The reaction mixture was cooled, 4 ml of water and 4 ml of saturated aqueous sodium hydrogencarbonate solution were added and the mixture was stirred for 10 mm. The suspension was filtered with suction and washed with water and three times with 2 ml each time of acetonitrile, and then the filtrate was lyophilized Yield: 51 mg (80% of theory).11161] LC/MS [Method 1]: R=0.81 mm; MS (ESIpos):mlz=534 (M+H),11162] ?H-NMR (400 MHz, DMSO-d6): oe [ppm]=10.90(s, 1H), 8.85 (d, 1H), 8.21 (dd, 1H), 8.05-8.00 (m 2H), 7.98(d, 1H), 7.75-7.67 (m, 2H), 7.56-7.50 (m, 2H), 6.51 (s, 1H),5.98 (dd, 1H), 3.80-3.62 (m, 5H), 2.53 (s, 3H)

The synthetic route of 145255-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ-NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; ACKERSTAFF, Jens; STAMPFUss, Jan; (87 pag.)US2017/291892; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 176526-00-4, 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 176526-00-4, name is 2-(Pyridin-4-yl)benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

6.5. Synthesis of (S)-2-Amino-3-(4-{6-[2,2,2-trifluoro-1-(2-pyridin-4-yl-phenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid Tetrabutylammonium fluoride (0.027 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 2-pyridin-4-yl-benzaldehyde (500 mg, 2.73 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (485 mul, 3.28 mmol) in 5 ml of THF at 0 C. The formed mixture was warmed up to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then treated with 5 ml of 1N HCl and stirred at room temperature overnight. The solvent was evaporated to dryness, 9 ml of 1M sodium carbonate aqueous solution was added, the aqueous phase was extracted with chloroform (3*10 ml), and the combined organic layer was washed with water, dried over MgSO4. The organic solvent was evaporated to give 300 mg of 2,2,2-trifluoro-1-(2-pyridin-4-yl-phenyl)ethanol, yield: 43%.

According to the analysis of related databases, 176526-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jin, Haihong; Shi, Zhi-Cai; Tunoori, Ashok; Wang, Ying; Zhang, Chengmin; Devasagayaraj, Arokiasamy; US2008/153852; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1256808-59-9, 5-Fluoro-3-methylpicolinic 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, 1256808-59-9, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Fluoro-3-methylpicolinic acid

5-Fluoro-3-methylpicolinic acid (200 mg, 1.29 mmol) was suspended in dichloromethane (4 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (435 mg, 300 mu, 3.43 mmol) as well as a drop of a mixture of dimethylformamide and toluene (1 :3, v/v) were added. The mixture was stirred for 1 h at room temperature. Then, it was concentrated in vacuo at 40C, the residue was treated with n-heptane (4 mL) and again concentrated and dried in vacuo (40C, 5 mbar) to afford 5-fluoro-3-methylpicolinoyl chloride as dark brown oil (220 mg). After that, tert-butyl ((4aR,5R,9R)-5-(6-amino-3-fluoropyridin-2-yl)-5,8,8-trimethyl- 9-oxido-2,3 ,4,4a,5 ,8-hexahydro- [ 1 ,4] thiazino [2, 1 -f] [ 1 ,2] thiazin-7-yl)carbamate (Int- 17 A A, 100 mg, 228 muiotaetaomicron) was dissolved in dichloromethane (4 mL), the solution cooled to 0-5C (ice bath) and N,N-diisopropylethylamine (75.5 mg, 100 mu, 584 muiotaetaomicron) was added, followed by a solution of 5-fluoro-3-methylpicolinoyl chloride (vide supra, 50 mg, 288 muiotaetaomicron) in dichloromethane (1 mL). The reaction mixture was stirred at 0-5C for 1.5 h. Then, ethanol (100 mu) was added, the mixture was stirred for 45 min at room temperature, poured onto a saturated aqueous solution of sodium hydrogencarbonate (15 mL) and extracted with dichloromethane (1 x 30 mL, 2 x 20 mL). The combined extracts were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 50 g, eluting with ethyl acetate / n-heptane, gradient 60:40 to 80:20) to afford, after drying in vacuo (50C, 5 mbar), the title compound as a white foam (115 mg, 88% yield). HPLC (method LCMS_gradient) tR = 3.2 min. 1H NMR (CDC13, 400 MHz): delta 1.48 (s, 9 H), 1.79 (s, 3 H), 1.80-2.01 (m, 3 H), 1.85 (s, 3 H), 1.96 (d, J = 1.2 Hz, 3 H), 2.31-2.48 (m, 1 H), 2.83 (s, 3 H), 3.35-3.45 (m, 1 H), 3.56-3.68 (m, 1 H), 4.07-4.14 (m, 1 H), 7.40 (ddd, J = 0.6, 2.7, 8.8 Hz, 1 H), 7.55 (dd, J = 8.9, 10.9 Hz, 1 H), 8.38 (d, J = 2.6 Hz, 1 H), 8.41 (dd, / = 3.0, 8.9 Hz, 1 H), 10.41 (br s, 1 H), 11.23 (br s, 1 H, exch). MS (ES+) m/z 577.3 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256808-59-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74695-44-6, 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. 74695-44-6, name is 5,7-Dichlorothieno[3,2-b]pyridine, molecular formula is C7H3Cl2NS, 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.

(1) A mixture of 5,7-dichlorotheno[3,2-b]pyridine (0.52 g), triethylamine (0.90 mL), 4-(methylsulfonyl)piperidine mono hydrochloride (0.62 g), and ethylene glycol (1.1 mL) was stirred at 120C for 6 h. Ethylene glycol (4.0 mL) and 1,4-dioxane (4.0 mL) were added, and the mixture was further stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried with anhydrous magnesium sulfate, and then silica gel was added to the organic layer. Silica gel and the desiccant were removed by filtration, the filtrate was concentrated under reduced pressure, and the resulting solids were washed with a mixture solution of ethyl acetate and diisopropyl ether. The resulting solids were purified by silica gel column chromatography (ethyl acetate/hexane = 1:1-1:0) to obtain 5-chloro-7-(4-(methylsulfonyl)piperidin-1-yl)thieno[3,2-b]pyridine (0.11 g).

According to the analysis of related databases, 74695-44-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2003131; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem