Category: pyridine-derivatives

Electric Literature of 76006-17-2 , The common heterocyclic compound, 76006-17-2, name is 1H-Pyrazolo[3,4-c]pyridin-3-amine, molecular formula is C6H6N4, 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.

Tert-butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-l-carboxylate (1.00 g, 3.34 mmol, 1.5 eq), 1H- pyrazolo[3,4-c]pyridin-3-amine (299 mg, 2.27 mmol, 1 eq) and potassium phosphate (945 mg, 4.45 mmol, 2 eq) were suspended in l-methoxy-2-propanol (10 mL) in a 20 mL microwave vial. The vial was capped and the mixture was heated in a microwave to 180C for 15 min. After cooling to RT, the suspension was diluted with water (20 mL) and neutralized (pH 7) by the addition of IN HCl. The precipitate was filterered, washed with water (10 mL) and dried for 16 h at 50C in vacuo to yield the title compound (169 mg, 75% purity, 16% of theory). LC-MS (Method IB): Rt = 0.73 min, MS (ESIPos): m/z = 370 [M+H]+

The synthetic route of 76006-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; CANCHO-GRANDE, Yolanda; BEYER, Kristin; ROeHRIG, Susanne; KOeLLNBERGER, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; WO2015/67549; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5470-22-4, 4-Chloropicolinic 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, Quality Control of 4-Chloropicolinic acid, blongs to pyridine-derivatives compound. Quality Control of 4-Chloropicolinic acid

General procedure: To a solution of the picolinic acid S7 (25.0 mmol) in DCM (100 mL) at room temperature was added SOCl2 (20 mL) and some drops of dry DMF. The reaction was allowed to stir at 50 C for 3 hours. The solvent was then removed under reduced pressure to afford the corresponding crude acid chloride (S8). Then DCM (40 mL) was added and the solution was cooled to 0C followed by dropwise addition of NEt3 (75.0 mmol, 3.0 eq) and N,O-dimethylhydroxylamine (50.0mmol, 2.0 eq). The reaction mixture was stirred at rt overnight, extracted by DCM, the organic layerwas dried over Na2SO4 and the solvent was evaporated, then purified by flash chromatography to gain the corresponding amides (S9).

The synthetic route of 5470-22-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jin, Liang; Yao, Qi-Jun; Xie, Pei-Pei; Li, Ya; Zhan, Bei-Bei; Han, Ye-Qiang; Hong, Xin; Shi, Bing-Feng; Chem; vol. 6; 2; (2020); p. 497 – 511;,
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.6231-18-1, name is 2,6-Dimethoxypyridine, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.Application In Synthesis of 2,6-Dimethoxypyridine

Comparative Example 1 In a 50 cc short-neck flask, 0.751 g of 2,6-dimethoxypyridine, 18 ml of 35% hydrochloric acid and 18 ml of acetic acid were placed, and then the flask was dipped in an oil bath of 140 C. while conducting stirring reflux for 1 hour. The reaction mixture was analyzed using liquid chromatography, showing a yield of 2,6-dihydroxypyridine of 28.8% and a residual ratio of the starting material (2,6-dimethoxypyridine) of 51.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6231-18-1, 2,6-Dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kato, Syunsaku; Suzuki, Daisuke; Seo, Yoshiko; US2002/157939; (2002); 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. 603305-89-1, name is 7-Bromothieno[3,2-b]pyridine. A new synthetic method of this compound is introduced below., COA of Formula: C7H4BrNS

General procedure: Compound N13z (24.45 mg, 0.118 mmol) in 1,4-dioxane (2 ml) was added Pd2(dba)3 (10.76 mg, 0.012 mmol), XantPhos (13.6 mg, 0.0235 mmol), 4-bromoquinoline (50 mg, 0.118 mmol), and DIPEA (61.4 muL, 0.353 mmol). The reaction vessel was degassed with argon, sealed, and heated to 110 C. overnight. The reaction mixture was then cooled to room temperature, filtered through Celite, and concentrated. The resulting residue was concentrated, diluted with 1:1 acetonitrile and water each containing 0.1% TFA and purified on preparatory HPLC (0 to 100% acetonitrile in water each containing 0.1% TFA). This provided Compound E78a as a TFA salt. LCMS ESI+ calc’d for C29H34N6O2S: 531.3 [M+H+]. found: 531.2 [M+H+].

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, 603305-89-1, 7-Bromothieno[3,2-b]pyridine.

Reference:
Patent; Gilead Sciences, Inc.; Chin, Gregory; Clarke, Michael O’ Neil Hanrahan; Han, Xiaochun; Hansen, Tim; Hu, Yunfeng Eric; Koltun, Dmitry; McFadden, Ryan; Mish, Michael R.; Parkhill, Eric Q.; Sperandio, David; Xu, Lianhong; Yang, Hai; (199 pag.)US2020/108071; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60832-72-6 ,Some common heterocyclic compound, 60832-72-6, molecular formula is C6H4N2O2, 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 the stirred solution of compound 2( 0.5 g,3.35 mmol )in DMF ( 3 ml )was added bromine(0.53g, 3.35 mmol ) at 0C.After 2h stirring at room temperature ,reaction mass was poured onto crushed ice, solid was followed out ,filtered the solid and dried under vacuum to get the desired compound 3 ( 0.25 g )

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60832-72-6, its application will become more common.

Reference:
Patent; VITAS PHARMA RESEARCH PRIVATE LIMITED; RANGARAJAN, Radha; KUMAR, Rajinder; PRABHAKAR, B V; CHANDRASEKHAR, P; MALLIKARJUNA, P; BANERJEE, Ankita; WO2013/42035; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 116922-60-2, 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.116922-60-2, name is 3-Bromo-4-fluoropyridine, molecular formula is C5H3BrFN, molecular weight is 175.9864, as common compound, the synthetic route is as follows.

2-(3-Bromo-4-fluorophenyl)-4,6-diphenyl-1 ,3,5-triazine E2 (1.0 equivalents), bis- (pinacolato)diboron, (1 .5 equivalents, CAS: 73183-34-3), tris(dibenzylideneacetone)dipalladium(0) Pd2(dba)3 (0.02 equivalents, CAS: 51364-51 -3), X- Phos (0.04 equivalents, CAS 564483-18-7) and potassium acetate (KOAc, 3.0 equivalents) are stirred under nitrogen atmosphere in dry toluene at 1 10 C for 16 h. After that time, 3- bromo-4-fluoropyridine (1 .0 equivalents, CAS 1 16922-60-2), K3P04 (aq) (3 equivalents) and extra portion of tris(dibenzylideneacetone)dipalladium(0) (0.02 equivalents, CAS: 51364-51 -3) and X-Phos (0.04 equivalents CAS 564483-18-7) are added to the hot reaction mixture. The reaction mixture is stirred at 1 10 C for 16 h. After cooling down to room temperature (RT) the reaction mixture is extracted with ethyl acetate/brine. The organic phases are collected, washed with brine and dried over MgSC . The organic solvent is removed, the crude product Z2 is purified by chromatography and obtained as a white solid (yield: 86 %).

The chemical industry reduces the impact on the environment during synthesis 116922-60-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CYNORA GMBH; SZAFRANOWSKA, Barbara; (135 pag.)WO2019/2355; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7321-93-9 , The common heterocyclic compound, 7321-93-9, name is 4,6-Dichloropyridin-3-amine, molecular formula is C5H4Cl2N2, 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.

In 0 °C, will 260ml2- bromine Ding added to the solution slowly acyl bromide 194g5-amino -2,4- two chloropyridine (CAS-No. 7321-93-9) and 388g potassium carbonate in 3.88l in ether in the suspension. The mixture is filtered, and the filter cake washing with ethyl ether. The filter cake is dissolved in methylene chloride, and the generated water and a solution of saturated sodium chloride solution. The organic phase is dried by sodium sulfate and concentrated in a vacuum. The residue with hexane, stirring, pumping the filtered again, and drying in a vacuum. Get 150g2-bromo-N-(4,6-dichloro-3-pyridyl) d amide.

The synthetic route of 7321-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharmaceuticals; Norbert, Schmees; Benjamin, Bader; Bernard, Haendler; Volker, Schulze; Ingo, Hartung; Niels, Bohnke; Florian, Puhler; (72 pag.)CN105555786; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5912-34-5, 3-(Cyanomethyl)picolinonitrile, 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, 5912-34-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(3) 8-bromo-l,7-naphthyridin-6-amine.; To a 50 mL round-bottomed flask was added hydrobromic acid, 30% in acetic acid (317 mul, 5868 mumol). 3-(cyanomethyl)picolinonitrile (280 mg, 1956 mumol) in AcOH (0.5 mL) was then added at 0 0C. The reaction mixture was stirred at 0 0C for 30 min. The solid was filtered out and washed with 50% EtOAc/hexanes. The solid was treated with sat. NaHCO3 (5 mL) and the mixture was extracted with EtOAc (2 x 50 mL). The organic extract was washed with satd NaCl (5 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 40% EtOAc/hexanes to give 8-bromo-l,7-naphthyridin-6-amine (312 mg, 71% yield). MS (ESI pos. ion) m/z calc’d for C8H6BrN3: 223.0, 225.0; found 224.0, 226.0. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 4.63 (s, 2 H) 6.61 (s, 1 H) 7.42 (dd, J=8.48, 4.09 Hz, 1 H) 7.85 (dd, J=8.48, 1.61 Hz, 1 H) 8.78 (dd, J=3.95, 1.61 Hz, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5912-34-5, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/155121; (2009); 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. 1003-73-2, name is 3-Methylpyridine 1-oxide, molecular formula is C6H7NO, 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. category: pyridine-derivatives

PREPARATION EXAMPLE 3 2-Chloro-5-methyl-pyridine A solution of 20 g (0.1 mol) of N,N-dipropylsulphamoyl chloride in 60 ml of chlorobenzene is added dropwise under nitrogen to a solution of 5.5 g (50 mmol) of 3-methylpyridine-1-oxide and 10.1 g (0.1 mol) of triethylamine in 40 mol of chlorobenzene. The mixture is then heated to 70° C. for a further 3 hours, the solid is then filtered off with suction, the filter cake is washed with chlorobenzene and the liquid phase is extracted using conc. hydrochloric acid.

With the rapid development of chemical substances, we look forward to future research findings about 1003-73-2.

Reference:
Patent; Bayer Aktiengesellschaft; US5099025; (1992); A;,
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. 88912-21-4, name is 6-Chloro-4-methoxypicolinic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Chloro-4-methoxypicolinic acid

Synthesis Example 19 Synthesis of N-[(2,6-Difluorophenyl)sulfonyl]-6-chloro-4-methoxy-2-pyridinecarboxamide [Compound (I-975)] Using 2,6-difluorobenzenesulfonamide [Compound (III-14)] (0.309 g, 1.6 mmol) and 6-chloro-4-methoxypicolinic acid [Compound (II-75)] (0.3 g, 1.6 mmol), the Compound (I-975) was synthesised according to the process of Synthesis Example 3. White solid, yield: 0.3129 g, percent yield: 54.0%, m.p.: 160-163 C. IR KBr cm-1: 3262, 1725, 1620, 1434, 1398, 1317, 1188, 1029, 891, 642. 1H-NMR (60 MHz, CDCl3, 6): 3.8 (3H, s, OCH3), 6.7-7.5 (4H, m, aromatic ring H*3, pyridine ring H), 7.43 (1H, d, J=2 Hz, pyridine ring H), NH indistinctness.

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, 88912-21-4, 6-Chloro-4-methoxypicolinic acid.

Reference:
Patent; Kureha Kagaku Kogyo K.K.; US6610853; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem