Month: April 2022

Synthetic Route of 52605-96-6, 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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.

A stirred solution of 2-chloro-3- methoxypyridine (4.86 g, 33.8 mmol) in hydrazine hydrate (40 mL) was heated under reflux for 1.5 hours. After cooling to RT, the reaction mixture was evaporated to dryness. The resulting residue was partitioned between 10% MeOH in CHCI3 and 40% w/v aqueous potassium carbonate. The aqueous phase was isolated and extracted twice with 10% MeOH in CHCI3. The combined organic extracts were dried (Na2S04), filtered and concentrated in vacuo to give the title compound (2.7 g, 57%) as a buff solid. H NMR (300 MHz, DMSO-d6): delta 7.65 (dd, J = 5.1 and 1.3 Hz, 1H), 6.99 (dd, J = 7.7 and 1.3 Hz, 1 H) overlapped with 6.98 (br s, 1 H), 6.56 (dd, J = 7.6 and 5.1 Hz, 1 H), 4.05 (br s, 2H), 3.76 (s, 3H). LCMS (Method A): RT = 0.34 nrtin, [M+H]+ = 140.

The chemical industry reduces the impact on the environment during synthesis 52605-96-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark Peter; O’DOWD, Colin Roderick; ZHANG, Lixin; TEVITT, Graham Peter; HARRISON, Timothy; BATTACHARYYA, Sumita; ROUNTREE, James Samuel Shane; BURKAMP, Frank; PRICE, Stephen; MACLEOD, Calum; ELLIOTT, Richard Leonard; SMITH, Phillip; BLENCH, Toby Jonathan; DYKE, Hazel Joan; WO2011/33265; (2011); A1;,
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. 887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine

A mixture of compound 2d2 (115.7 g, 400 mmol) and PhPOCl2 (668.6 g, 343 mmol) under N2 is stirred at 136 C. overnight, then cooled to room temperature and added slowly to 3 L of crushed ice. The aqueous mixture is adjusted to pH 6 and filtered. The aqueous filtrate is extracted with DCM (3 L) then the organic phase is washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated to provide compound 2d3.

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, 887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine.

Reference:
Patent; Beaulieu, Pierre L.; Coulombe, Rene; Fazal, Gulrez; Goulet, Sylvie; Poirier, Martin; Rancourt, Jean; Stammers, Timothy; Thavonekham, Bounkham; US2008/45516; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 628691-93-0, 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 628691-93-0 as follows.

2-Chloro-N-(4-(4,4-difluoropiperidin-1-yl)pyridin-3-yl)-3-fluoroisonicotinamideIn a 15 mL vial was dissolved 4-(4,4-difiuoiOpiperidin-l- yl)pyridin-3-amine (139 mg, 0.650 mmol) and 2-chloro-3-fluoroisonicotinic acid (103.8 mg, 0.591 mmol) in dimethylformamide (4 mL) to give a tan solution. HATU (450 mg, 1.183 mmol) and Hunig’s base (0,207 mL, 1,183 mmol) were added, and the mixture was stirred at rt for 22 h. It was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified using silica gel flash chromatography, eluting with 50% ethyl acetate/hexane to afford the desired product (31.8 mg, 14.5%) as a tan oil: MS (ESI) (m/z) 371 (M+H)+; 1H NM (400 MHz, MeOD) delta 9.14 (s, lH)t 8.37 (d, J = 5.0 Hz, 1H), 8.30 (dd, J = 4.6, 3.7 Hz, 1H), 7.81 (t, J = 4.9 Hz, 1H), 7.39 (dd, J = 8.4, 4.4 Hz, 1H), 7.19 (d, J = 5.8 Hz, 1H), 3.38 – 3.31 (m, 2H), 3.25 – 3.18 (m, 2H), 2.16 – 2.02 (m, 2H), 2.01 – 1.91 (m, 2H); 1 F NMR (376 MHz, MeOD) delta -73.28 (s), -75.17 (s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628691-93-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69593; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 109880-43-5, 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. 109880-43-5, name is Methyl 4-chloro-6-(hydroxymethyl)picolinate. A new synthetic method of this compound is introduced below.

Example 37: 4-Chloro-6-r(5-chloro-2-{r(4-chloro-2-fluorophenyl)- methvnoxy>phenyl)methvn-2-pyridinecarboxylic acid, sodium salt; Methyl 4-chloro-6-(chloromethvD-2-pyridinecarboxylate; To a solution of methyl 4-chloro-6-(hydroxymethyl)-2-pyridinecarboxylate (166 mg, Ref: Kittika et a/., Tetrahedron, 44 (10), 2821 , (1988)) in dry dichloromethane (3ml) was added thionyl chloride (66 mul). The solution was stirred for 40 minutes. LC/MS indication reaction completion. Solvent was removed u.r.p. (under reduced pressure) to give a white solid. Toluene (~2 ml) added then removed u.r.p. The residue was dried in vacuo to give a white solid. (175 mg, 97%). LC/MS [MH+] = 220 / 222, Rt = 2.51 min. Title compound obtained as the free base.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109880-43-5, Methyl 4-chloro-6-(hydroxymethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/66968; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-82-0, 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. 884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid, molecular formula is C7H6FNO3, 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.

[0285] A mixture of 5-fluoro-2-methoxynicotinic acid (100 rng, 584 umol) and DMF (4.27 mg, 58.44 umol, 4.50 uL) in DCM (2 mL) was added oxalyl dichloride (222.52 mg, 1.75 mmol, 153.46 uL) at 0C. The reaction mixture was stirred at 25C for 1.5 hours and then concentrated under reduced pressure to give the title compound as a light yellow solid, which was used without further purification (97 mg, 88%).

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 884494-82-0, 5-Fluoro-2-methoxynicotinic acid.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 955376-51-9 , The common heterocyclic compound, 955376-51-9, name is 6-Methoxyimidazo[1,2-a]pyridine, molecular formula is C8H8N2O, 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 solution of 6-methoxyimidazo[1,2-a]pyridine (15.0 g) in methanol (200 mL)was added Pd(OH)2 (1.4 g) and AcOH (0.6 mL). The mixture was stirred at 60C for 16 hours under H2 (40 psi). The mixture was filtered. The filtrate was concentrated in vacuo to afford 6- methoxy-5,6,7,8-tetrahydroimidazo[1 ,2-a]pyridine (16.0 g). MS(ES) mlz 153 (MH).

The synthetic route of 955376-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEN, Weichun; IGBOKO, Ebere F; LIN, Xichen; LU, Hongfu; REN, Feng; WREN, Paul Bryan; XU, Zhongmiao; YANG, Ting; ZHU, Lingdong; WO2015/181186; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1227270-32-7, 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. 1227270-32-7, name is 2-Iodo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5IN2, 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.

Compound 2 (1.5 g, 6.15 mmol), copper iodide (118 mg, 0.62 mmol), bis(triphenylphosphine)palladium(II) dichloride (217 mg, 0.31 mmol), triethylamine (1.28 mL, 9.23 mmol), ethynyl(trimethyl)silane (1.30 mL, 9.23 mmol) and THF (35 mL) were introduced in an oven dried round bottom flask under inert atmosphere. The mixture was stirred at room temperature for 20 h. The reaction mixture was diluted with EtOAc and filtered on Dicalite. The filtrate was washed with water and a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel column, cyclohexane/EtOAc 7:3, to give 1.099 g of the clean expected product as a beige solid in 84% yield. 4.2.9 2-((Trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridine (3c) The derivative 3c was synthesized following the general procedure for the Sonogashira coupling reaction from 7. The crude product was purified by chromatography on silica gel column, cyclohexane/EtOAc 98:2, to give 381 mg of the clean expected product as an orange solid in 86% yield. 1H NMR (300 MHz, DMSO-d6) delta (ppm): 12.14 (brs, 1H), 8.27 (dd, J = 1.5, 4.7 Hz, 1H), 7.93 (ddd, J = 0.6, 1.5, 7.9 Hz, 1H), 7.09 (dd, J = 4.7, 7.9 Hz, 1H), 6.77 (sd, J = 2.0 Hz, 1H), 0.27 (s, 9H). 13C NMR (75 MHz, DMSO-d6) delta (ppm): 148.5, 145.2, 129.1, 119.6, 119.2, 116.9, 107.4, 99.2, 98.0, 0.2 (3C).

According to the analysis of related databases, 1227270-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Baltus, Christine B.; Jorda, Radek; Marot, Christophe; Berka, Karel; Bazgier, Vaclav; Kry?tof, Vladimir; Prie, Gildas; Viaud-Massuard, Marie-Claude; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 701 – 719;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17282-01-8, 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.17282-01-8, name is 3-Bromo-2-fluoro-5-picoline, molecular formula is C6H5BrFN, molecular weight is 190.01, as common compound, the synthetic route is as follows.

[Step 2] Production of 4-(2-fluoro-5-methylpyridin-3-yl)-2-(pyridin-2-ylme thoxy)-5,6,7,8-tetrahydroquinoline To 2-(pyridin-2-ylmethoxy)-4-(4,4,5,5-tetramethyl-1,3, 2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline (50 mg), 3-bromo-2-fluoro-5-methylpyridine (34 mg), Pd(dppf)Cl2·CH2Cl2 (9 mg) and potassium carbonate (57 mg) was added 1,4-dioxane/water (3/1, 1.3 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 6 hours. After the reaction mixture was allowed to return to room temperature, diluted with AcOEt, dried over anhydrous sodium sulfate, filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (30 mg) as a white solid. [MS (ESI) m/z 350.4 (M+H)+]

Statistics shows that 17282-01-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-fluoro-5-picoline.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; TSUJI, Takashi; SHIRAI, Masaaki; EP2891656; (2015); A1;,
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. 856013-04-2, name is 6-Bromopyridine-2-sulfonamide, molecular formula is C5H5BrN2O2S, 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. COA of Formula: C5H5BrN2O2S

Under argon, 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyridine (0.2 g, 0.74 mmol, prepared by the methods described in WO 2011/045224), 6-bromopyridin-2-sulphonamide (0.175 g, 0.74 mmol) and tetrakis(triphenylphosphine)palladium (0.025 g, 0.022 mmol) were added to a mixture, degassed by means of argon, of sodium carbonate solution in water (2.9 ml, 2 M/L) and acetonitrile (4 ml). The reaction mixture was stirred at 70 C. for 18 h. After cooling, the reaction mixture was poured onto water and the precipitated crystals were filtered off with suction. They were subsequently stirred with diethyl ether and filtered off with suction. This gave 0.23 g (97% of theory) of 6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide.HPLC-MS: LogP(HCOOH): 0.99; mass (m/z): 302.1 (M+H)+ 1H NMR (d6-DMSO): 7.43 (s, 2H), 7.60-7.63 (m, 1H), 7.76 (d, 1H), 8.00 (d, 1H), 8.11 (t, 1H), 8.28-8.31 (m, 1H), 8.53 (s, 1H), 8.58-8.60 (m, 1H), 9.16-9.17 (m, 1H), 9.33 (s, 1H) ppm

With the rapid development of chemical substances, we look forward to future research findings about 856013-04-2.

Reference:
Patent; BAYER CROPSCIENCE AG; US2012/165345; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 103058-87-3, 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. 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde. A new synthetic method of this compound is introduced below.

(5-bromo-2-methoxypyridin-3-yl)methanol 5-Bromo-2-methoxynicotinaldehyde (2 g, 9.26 mmol) was suspended in CH3OH (40 mL) and the mixture was cooled to 0 C. Sodium borohydride (0.350 g, 9.26 mmol) was added in one portion, causing bubbling. The reaction mixture stirred at 0 C. for 15 minutes, then the flask was removed from the ice bath and allowed to stir at room temperature for 2 hours. The reaction mixture was then concentrated in vacuo, and the crude material was taken up in methyl tert-butyl ether and saturated aqueous NaHCO3 solution. The phases were separated, and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound, (1.876 g, 93% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.15 (d, J=2.5 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 4.66 (d, J=6.2 Hz, 2H), 3.99 (s, 3H), 2.15 (t, J=6.3 Hz, 1H); MS (DCI+) m/z 217.8 (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,103058-87-3, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Greszler, Stephen N.; Housseman, Christopher Gaetan; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (263 pag.)US2018/99931; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem