Pyridine-derivatives

Electric Literature of 89809-63-2, Adding some certain compound to certain chemical reactions, such as: 89809-63-2, name is 5-Methoxypicolinonitrile,molecular formula is C7H6N2O, 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 89809-63-2.

Using the general procedure for the synthesis of amidoximes, 2-cyano-5-methoxypyridine (270 mg, 2.01 mmol), a solution of hydroxylamine hydrochloride (0.457 ml of 5 M, 2.28 mmol) in ethanol (4 mL), and sodium hydroxide (0.230 mL of 10 N, 2.30 mmol) were heated at reflux for 24 hours. Standard work up afforded 79 mg (24%) of 5-methoxypyrid-2-ylamidoxime.

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. 89809-63-2, 5-Methoxypicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wagenen, Bradford Van; Stormann, Thomas M.; Moe, Scott T.; Sheehan, Susan M.; McLeod, Donald A.; Smith, Daryl L.; Isaac, Methvin Benjamin; Slassi, Abdelmalik; US2003/55085; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 951625-93-7, 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 951625-93-7, name is Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of methyl 4-chloro-l-tosyl-lH-pyrrolo[2,3-b]pyridine-5-carboxylate:Sodium hydride (341 mg, 8.53 mol, 1.2 eq) was added in portions to a solution of methyl 4- chloro-lH-pyrrolo[2,3-b]pyridine-5-carboxylate (1.5 g, 7.1 mmol, 1.0 eq) in THF (20 mL). The suspension was stirred at 0 C for 30 min, then a solution of 4-methylbenzene-l-sulfonyl chloride (2.7 g, 14.2 mmol, 2.0 eq) in THF (10 mL) was added at 0 C. The resulting suspension was stirred at this temperature for 15 min and 1 h at room temperature. The suspension was filtered through Celite. The filtrate was diluted with EtOAc (200 mL), washed with brine (100 mL x 3). The combined organic layer was dried (MgS04) and concentrated in vacuo to afford a residue which was purified by silica gel column chromatography (PE/EA = 10:1) to give 128.5 a white solid (1.6 g, yield: 60%). XH NMR (400 MHz, DMSO-J6) delta: 8.84 (s, 1H), 8.12 (d, 1H), 8.06 (d, 2H), 7.46 (d, 2H), 6.98 (d, 1H), 3.93 (s, 3H), 2.39 (s, 3 H). ESI-MS: 365.0 (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 951625-93-7, Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; SCOTT, Daniel; CONLON, Patrick; JENKINS, Tracy, J.; POWELL, Noel; GUAN, Bing; CURERVO, Julio, H.; WANG, Deping; TAVERAS, Art; WO2012/58645; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 853909-08-7, 5-Ethynyl-2-fluoropyridine, 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, 853909-08-7, blongs to pyridine-derivatives compound. HPLC of Formula: C7H4FN

A solution of 5-ethynyl-2-fluoro-pyridine (500 mg, 4.13 mmol), l-Boc-piperazine (923 mg, 4.95 mmol) and triethylamine (1.15 mL, 8.26 mmol) in MeCN (10 mL) was stirred at 60 C for 16 h. The reaction was poured into H20 (50 mL) and extracted with EtOAc (70 mL). The organic layer was separated, dried over Na2S04, filtered and concentrated under vacuum The residue was purified by silica gel chromatography (petroleum ehtenEtOAc, 10: 1 to 2: 1) to afford /e/ -butyl 4-(5-ethynyl-2-pyridyl)piperazine-l-carboxylate (630 mg, 79%) as white solid. lH NMR (CHLOROLORM-d, 400 MHz) d 8.24 (d, 1H, 7=2.2 Hz), 7.48 (dd, 1H, 7=2.3, 8.9 Hz), 6.48 (d, 1H, J= 8.8 Hz), 3.4-3.5 (m, 8H), 3.00 (s, 1H), 1.41 (s, 9H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,853909-08-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BORRONI, Edilio; GOBBI, Luca; HONER, Michael; EDELMANN, Martin; MITCHELL, Dale; HARDICK, David; SCHMIDT, Wolfgang; STEELE, Christopher; MULLA, Mushtaq; (151 pag.)WO2019/121661; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 61494-55-1, 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 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows.

INTERMEDIATE 52-[(2-Fluoro-4-iodophenyl)amino1thienor2,3-&]pyridine-3-carboxylic acidTo a stirred solution of diisopropylamine (35.3 mL, 250 mmol) in anhydrous THF (200 mL) cooled to -150C was added rc-butyllithium (100 mL, 2.5M in hexanes, 250 mmol) slowly such that an internal temperature of between -10 and 00C was maintained. The resultant mixture was stirred at room temperature for 15 minutes before being cooled to O0C. The solution of lithium diisopropylamide was added via cannula to a rapidly stirred suspension of (2-chloropyridin-3-yl)acetic acid (Intermediate 3; 21.4 g, 125 mmol) in anhydrous THF (400 mL) at 00C. The temperature of the reaction mixture was maintained at 00C over the course of the addition. Upon complete addition of the lithium diisopropylamide solution the resultant bright yellow suspension was stirred at 00C for 15 minutes. A solution of Intermediate 4 (34.9 g, 125 mmol) in anhydrous THF (200 mL) was then added to the reaction mixture via cannula and the mixture heated to 65 C for 18 hours. The reaction mixture was cooled and the volatiles removed in vacuo. The resultant brown gum was redissolved in THF (200 mL), cooled to O0C and 10% aqueous acetic acid (500 mL) added slowly. Acetonitrile (-200 mL) was added slowly until a brown solid developed; the solid was isolated by filtration and washed with successive portions of diethyl ether and acetonitrile to give the title compound as a yellow crystalline solid (11.0 g, 21%). ?H (DMSOd6) 8.42 (IH, d, J 6.7 Hz), 8.22 (IH, m), 7.73 (IH, m), 7.61 (IH, m), 7.46 (IH, t, J8.6 Hz), 7.35-7.31 (IH, m). Exchangeable protons were not observed. LCMS (pH 10) RT 1.82 minutes, ES+ 415 (M+H)+, ES” 413 (M-H)”.

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2009/13462; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 956010-87-0, 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 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1(2)3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine 7-oxide (1b)Compound (1a) was dissolved in ethylene glycol dimethyl ether (100 mL) and heptane (200 mL), and m-chloroperoxybenzoic acid (33.9 g) was added to the resulting solution at 0 C., followed by stirring at room temperature for 1 hr. The precipitate was collected by filtration to obtain compound (1b) (33.3 g, 96%) as a white solid.1H-NMR (DMSO-d6) delta 8.53 (1H, d, J=6.1 Hz), 8.87 (1H, d, J=8.3 Hz), 7.36 (1H, dd, J=8.3, 6.1 Hz); LRMS (ESI) m/z 204 [M+H]+.

According to the analysis of related databases, 956010-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63237-88-7, Adding some certain compound to certain chemical reactions, such as: 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid,molecular formula is C8H6N2O2, 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 63237-88-7.

To a solution of pyrazolo[1,5-a]pyridine-2-carboxylic acid (2.40 mg, 14.8 mumol) and 8 (6.00 mg, 14.8 mumol) in anhydrous DMF (1 mL) was added DIPEA (5.00 muL, 29.6 mumol) and HATU (5.90 mg, 15.5 mumol). After stirring the reaction mixture at room temperature for 16 h the solvent was removed under reduced pressure. The crude mixture was suspended in aqueous 5% NaHCO3 solution and extracted with ethyl acetate (3*). The combined organic phases were washed with water and brine and were dried (MgSO4). After removal of solvents under reduced pressure the crude material was purified by preparative HPLC (acetonitrile in 0.1% aqueous HCOOH, 5% to 95%) to give 3 (2.25 mg, 28%) as a colorless solid. 1H NMR (600 MHz, CDCl3) delta 8.38-8.34 (m, 1H), 7.61-7.57 (m, 1H), 7.31 (br t, J = 5.2 Hz, 1H), 7.16 (ddd, J = 8.9, 6.7, 1.0 Hz, 1H), 7.07 (d, J = 0.6 Hz, 1H), 6.87 (td, J = 6.9, 1.3 Hz, 1H), 6.60 (s, 1H), 3.75 (br s, 4H), 3.55 (app q, J = 6.6 Hz, 2H), 2.55 (br s, 4H), 2.48 (br s, 2H), 1.77-1.61 (m, 4H), 1.36 (s, 9H); 13C NMR (150 MHz, CDCl3) delta 177.7, 162.2, 154.9 (q, JCF = 33.7 Hz), 148.0, 141.4, 128.3, 123.7, 121.3 (q, JCF = 275 Hz), 119.3, 113.6, 98.0, 95.6 (q, JCF = 3.4 Hz), 57.9, 52.7, 43.8, 39.5, 39.1, 29.7, 29.4, 27.6, 24.2; ESI-MS m/z 504.3 [M+H]+; HRMS-ESI (m/z): [M+H]+: calcd. for C25H33F3N7O: 504.2693, found: 504.2688; HPLC: System 1: tR = 16.3 min, purity 99%, System 2: tR = 16.2 min, purity 99%.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stoessel, Anne; Brox, Regine; Purkayastha, Nirupam; Huebner, Harald; Hocke, Carsten; Prante, Olaf; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3491 – 3499;,
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.1193-71-1, name is 4,6-Dimethylpyridin-3-amine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.Formula: C7H10N2

4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (247 mg, 0.819 mmol) was added to a solution of triethylamine (0.114 mL, 0.819 mmol) and 4,6-dimethyl-3-pyridinamine (100 mg, 0.819 mmol) in dichloromethane (1 mL). The mixture was heated at 70 C. for 2 hours. To the mixture was added water (5 mL) then the organic layer separated and purified by silica (Si) chromatography (100% ethyl acetate). The relevant fractions were combined and concentrated to give the title product (310 mg) as a yellow solid. LCMS (2 min, formic) Rt 0.63 mins, m/z (ES+) 388 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-71-1, 4,6-Dimethylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; Birault, Veronique; Campbell, Amanda Jennifer; Harrison, Stephen; Le, Joelle; Shukla, Lena; US2015/65507; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915006-52-9, 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 915006-52-9 as follows.

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%). To a mixture containing 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) and Intermediate 5A-2 (100 mg, 0.29 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (111 mg, 0.36 mmol), and Pd(dppf)C12 (10.5 mg, 0.014 mmol) in a screw cap vial was added THF (2.5 mL) followed by 3M aqueous solution of tripotassium phosphate (0.10 mL, 0.3 mmol). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 75 C. for 3 h. The reaction mixture was cooled to room temperature and treated with saturated aqueous NaCl solution (5 mL) and extracted with ethyl acetate (3*10 mL). The extracts were combined, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in a small amount of DCM and purified on silica gel column chromatography eluting with a 10 min gradient from 5%-100% DCM/EtOAc. No separation was observed. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate was isolated (100 mg, 77% yield), m/z (550, M+1) and was used as such in subsequent step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,915006-52-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3222-56-8, 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. 3222-56-8, name is 2-Methylnicotinic acid. A new synthetic method of this compound is introduced below.

General procedure: To a solution of carboxylic acid 22 or 29?31 (0.1mol) in dry methanol (150mL), concd H2SO4 (20mL) was added. The mixture was refluxed for 15?20h (LC?MS control). The solvent was removed in vacuo, and the residue was dissolved in H2O. The solution was made alkaline with cold saturated aq K2CO3 and extracted with CH2Cl2 (4×50mL). The combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography (EtOAc as eluent) or distilled in vacuo to give 17?20.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3222-56-8, 2-Methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Article; Yaremenko, Anatoliy G.; Volochnyuk, Dmitriy M.; Shelyakin, Vyacheslav V.; Grygorenko, Oleksandr O.; Tetrahedron; vol. 69; 33; (2013); p. 6799 – 6803;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1256823-07-0 ,Some common heterocyclic compound, 1256823-07-0, molecular formula is C7H5BrN2O, 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 3. Preparation of 4-methoxy-5-(4-methyl-1 /-/-imidazol-1 -yl)pyridine-2- carbonitrile (C3). 4-Methyl-1 /-/-imidazole (15 g, 0.18 mol), potassium carbonate (34 g, 0.25 mol) and 18-crown-6 (64 g, 0.24 mol) were combined in acetonitrile (600 mL), and the reaction mixture was heated to 60 C for 2 hours. 5-Bromo-4- methoxypyridine-2-carbonitrile (C2) (25 g, 0.12 mol) was added in one portion, and the reaction was heated to reflux for 18 hours. After being combined with an identical reaction mixture, the reaction was partitioned between water (500 mL) and ethyl acetate (500 mL). The aqueous layer was extracted with ethyl acetate (2 x 300 mL), and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by chromatography on silica (Gradient: 1 :10 to 1 :2 ethyl acetate: petroleum ether) provided the title product as a white solid. Yield: 8.2 g, 0.038 mol, 16%. NMR (400 MHz, CDCI3) delta 2.30 (d, J=1 Hz, 3H), 4.02 (s, 3H), 6.96-6.97 (m, 1 H), 7.38 (s, 1 H), 7.82 (d, J=1.5 Hz, 1 H), 8.53 (s, 1 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. 1256823-07-0, 5-Bromo-4-methoxypicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; AM ENDE, Christopher William; JOHNSON, Douglas Scott; O’DONNELL, Christopher John; PETTERSSON, Martin Youngjin; SUBRAMANYAM, Chakrapani; WO2011/48525; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem