Pyridine-derivatives

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.896722-51-3, name is 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C14H12N2O2S, molecular weight is 272.32, as common compound, the synthetic route is as follows.Quality Control of 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

A solution of 50% NaOH (0.573 g) was added to N-protected 6-methyl-7-azaindole (0.390 g, 1.43 mmol) in Ethanol (10 mL). After refluxed for 8 h, the mixture was concentrated and was extracted with CHCl3. The organic layer was washed with water and dried. The solvent was evaporated in vacuo and the residue was purified on a silica gel column eluting with EtOAc/hexane (1:3) to give 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.148 g, 78%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,896722-51-3, 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 134363-45-4, 2-(Pyridin-3-yl)benzoic 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 C12H9NO2, blongs to pyridine-derivatives compound. Computed Properties of C12H9NO2

A mixture of [2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1 -yl]-lambda/-ethyl-2- phenyl-acetamide (320 mg, 0.90 mmol), 2-(3′-pyridyl) benzoic acid (200 mg, 0.99 mmol) and HATU (375 mg, 0.99 mmol) in DMF (10 ml_) was treated with DIPEA (170 mul_, 0.99 mmol) and let stir at room temperature for 6 h. The reaction mixture was quenched with H2O and extracted with EtOAc. The organic layer was separated and washed (sat’d NaHCO3, brine), dried (Na2SO4), filtered and concentrated to yield a semi solid, which was purified by PTLC (5% 2M NH3/MeOH in CH2CI2) to yield the title compound as a brown foam.MS (ESI): mass calcd. for C32H32FN5O;?, 537.64; m/z found, 538.5 [M+H]+. 1H NMR (CDCI3): 8.74-8.73 (m, 1 H), 8.62-8.60 (m, 1 H), 7.80-7.76 (m, 2H), 7.60-7.57 (m, 1 H), 7.54-7.50 (m, 1 H), 7.46-7.43 (m, 1 H), 7.33-7.29 (m, 6H), 7.18-7.15 (m, 1 H), 7.09-7.00 (m, 2H), 6.91 (s, 1 H), 6.84-6.77 (m, 1 H), 3.87 (s, 1 H), 3.35-3.32 (m, 2H), 3.05-3.04 (m, 4H), 2.61 -2.58 (m, 4H), 1.16 (t, J = 7.2, 3H)

The synthetic route of 134363-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2009/6185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84199-61-1 , The common heterocyclic compound, 84199-61-1, name is 3-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, 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 1. 2-Bromo-l-(2-bromopyridin-3-yl)ethanone A solution of l-(2-bromopyridin-3-yl)ethanone (2.10 g, 10.5 mmol) in acetic acid (28.0 mL) was treated with bromine (595 L, 11.5 mmol) and heated at 90 C for 1 h. The reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was separated and further extracted with ethyl acetate (2 x 80 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography (10% ethyl acetate/hexanes to 30% ethyl acetate/hexanes) gave the desired product (2.15 g, 73%). LCMS calculated for C7H6Br2NO (M+H)+: m/z = 277.9, 279.9, 281.9; found: 277.7, 279.7, 281.8.

The synthetic route of 84199-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew P.; SPARKS, Richard B.; MADUSKUIE, Thomas P. Jr.; RODGERS, James D.; WO2014/143768; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, 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, SDS of cas: 60010-03-9, blongs to pyridine-derivatives compound. SDS of cas: 60010-03-9

A suspension of 2,6-dichloro-4-methyl-3-nitropyridine (300 mg, 1.449 mmol) and sodium bicarbonate (243 mg, 2.90 mmol) in Tetrahydrofuran (THF) (20 mL)) was added (S)- dimethyl 2-aminosuccinate hydrochloride (430 mg, 2.174 mmol) at 0 C under nitrogen. Then the reaction mixture was stirred at 65 C for 24 hr. The reaction was monitored by TLC. The reaction mass filtered and washed with EtOAc (2 x 30 mL). The filtrate was concentrated under reduced pressure to give the crude material. The crude product was added to a neutral alumina column and was eluted with Hex/EtOAc (9: 1). Collected fractions were concentrated under reduced pressure to afford the desired product (250 mg, 0.742 mmol, 51.2 % yield) as yellow gummy liquid, LCMS (m/z) 339.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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