Pyridine-derivatives

Reference of 503000-87-1 ,Some common heterocyclic compound, 503000-87-1, molecular formula is C7H6ClNO3, 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.

The intermediate 2-chloro-6-methoxynicotinic acid (3.0 g, 16.00 mmol, 1.0 eq),Potassium carbonate (2.48g,17.94 mmol, 1.1 eq) and methyl iodide (3.07 g, 21.6 mmol, 1.4 eq)Add to DMF solution (35mL), heat to 50 CReaction for 12 hours. The reaction was completely detected by LC-MS and was cooled to room temperature.The reaction solution was directly concentrated under reduced pressure.The crude product was purified by silica gel column chromatography (100-200 mesh silica gel)The product was obtained as a white solid (1.5 g, yield: 47%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,503000-87-1, its application will become more common.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; (67 pag.)CN109810041; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1374655-69-2, 3-Bromo-4-ethyl-5-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, 1374655-69-2, blongs to pyridine-derivatives compound. Formula: C7H7BrFN

To a stirred solution of 9-chloro-8-fluoro-l-methyl-7-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-4,5-dihydro-[l,2,4]triazolo[4,3-a]quinoline (151-3; 0.4 g, 0.0011 mol) and 3-bromo-4-ethyl-5-fluoropyridine (0.22 g, 0.0011 mol) in the mixture of 1,4-dioxan (15 ml) and water (5 ml) was added cesium carbonate (0.71 g, 0.0022 mol). Reaction mass was purged with argon for 20 min. Then Pd(dppf)2Cl2 (0.04 g, 0.000055mol) was added. The reaction mixture was heated 95 C and stirred at 95 C for 6 h. The reaction mixture was allowed to cool to room temperature, the reaction mixture was filtered through celite bed and filter bed was thoroughly washed with ethyl acetate. The filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane, washed with water, brine solution, dried over sodium sulphate, concentrated to afford the crude compound, which was purified by silica gel (60-120) column chromatography and preparative HPLC (analytical conditions: column: XTERRA C18(250mm X 4.6mm X 5um), mobile phase (A): 0.01% ammonia in water, mobile phase (B): acetonitrile, flow rate: 1.0 mL/min, Time/%B: 0/20,8/50,25/50,26/20,30/20) to obtain title compound (76). 1H MR (400 MHz, DMSO-c ) 6: 8.61 (s, 1 H), 8.33 (s, 1 H), 7.62-7.60 (d, J=7.2 Hz, 1 H), 2.91 (bs, 4 H), 2.58 (s, 3 H) 2.57-2.54 (m, 2 H), 1.06-1.02 (t, J = 7.6 Hz, 3 H). MS (M+l): 361.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1374655-69-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 870997-87-8, 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. 870997-87-8, name is 2-Amino-N-methylnicotinamide. A new synthetic method of this compound is introduced below.

Example 1, Step A, Method A and Method B; A 500 ml round bottomed flask was charged with methyl 2- aminopyridine 3-carboxamide 1 (4.5 g, 29.76 mmol) and 1 ,2-dichloroethane(150 ml). The resulting solution was cooled to -40 C while triphosgene (7 g,23.59 mmol) was slowly added. Triethylamine (4.4 g, 43.48 mmol) was then added via a syringe dropwise at this temperature. The reaction mixture was stirred at -40 C for two hours before warming up gradually to room temperature and maintained at this temperature overnight. The suspension was treated with water (100 ml) and saturated sodium carbonate (100 ml) and separated. The aqueous solution was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated on rotavapor. The residue was dried under house vacuum to provide a deep tan solid (4.1 g). This material was mixed with phosphorus oxychloride (50 ml) in a 250 ml flask. The resulting suspension was refluxed for 4 hours. The excess phosphorus oxychloride was removed by distillation under reduced pressure. The residue was dissolved in methylene dichloride (200 ml) and poured into ice (50 g). The suspension was neutralized with saturated sodium carbonate solution and separated. The organic layer was dried over sodium sulfate, concentrated, and dried under vacuum to afford a black gel (1.4 g), which was used directly for the next reaction without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,870997-87-8, 2-Amino-N-methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA, INC.; WO2008/79279; (2008); 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. 80537-07-1, name is 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid

EXAMPLE 56 STR64 Thionyl chloride (240 mg) was added dropwise to a stirred mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid [compound (I)](320 mg) and N,N-dimethylformamide (one drop) in chloroform (10 ml), and then stirred under reflux for 4 hours. After cooling the mixture, chloroform was evaporated in vacuo to give acid chloride of compound (I). Triethylamine (338 mg) was added to a suspension of the acid chloride of compound (I) in methylene chloride (10 ml) under ice-cooling, and to this suspension a solution of 2-ethylpiperidine in methylene chloride was added dropwise. The mixture was stirred under ice-cooling and stood at room temperature overnight. Saturated sodium chloride aqueous solution (20 ml) was added to the mixture and extracted with chloroform (20 ml). The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (8 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-(2-phenylpyrazolo[1,5-a]pyridin-3-ylcarbonyl)-2-ethylpiperidine (263 mg). mp 182-183 C. IR (Nujol): 1630, 1600, 1520 cm-1 NMR (DMSO-d6, delta): 0.69 (3H, t, J=7.0 Hz), 1.12-1.93 (8H, m), 2.73-3.17 (1H, m), 3.69-4.45 (2H, m) 7.07 (1H, td, J=7.0 Hz and 2.0 Hz), 7.29-8.00 (7H, m), 8.86 (1H, dd, J=7.0 Hz and 1.0 Hz) Analysis Calcd. for C21 H23 N3 O: C 75.65, H 6.95, N 12.60. Found: C 75.75, H 7.01, N 12.66.

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, 80537-07-1, 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid.

Reference:
Patent; Fujisawa Pharmaceutical Company, Ltd.; US4925849; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75279-39-9 , The common heterocyclic compound, 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide, molecular formula is C7H9N3O, 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.

General procedure: To a solution of 9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-6-phenoxy-9H-Purine (500 mg, 1.181 mmol) and 3-fluoropyridin-4-amine (529 mg, 4.72 mmol) in DMF (5 mL) was added a 60% dispersion of sodium hydride (236 mg, 5.90 mmol) in mineral oil and the mixture was stirred for 3 h. LCMS indicated completion of reaction. The reaction mixture was quenched carefully with water (25 mL) and allowed to stand for two hours. The resulting brown precipitate was filtered and washed with water followed by petroleum ether and dried to afford N-(3-fluoropyridin-4-yl)-9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-9H-purin-6-amine (400 mg, 0.634 mmol, 53.7 % yield) as a brown solid

The synthetic route of 75279-39-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Harikrishnan, Lalgudi S.; Warrier, Jayakumar; Tebben, Andrew J.; Tonukunuru, Gopikishan; Madduri, Sudhakara R.; Baligar, Vishweshwaraiah; Mannoori, Raju; Seshadri, Balaji; Rahaman, Hasibur; Arunachalam; Dikundwar, Amol G.; Fink, Brian E.; Fargnoli, Joseph; Fereshteh, Mark; Fan, Yi; Lippy, Jonathan; Ho, Ching-Ping; Wautlet, Barri; Sheriff, Steven; Ruzanov, Max; Borzilleri, Robert M.; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 1026 – 1034;,
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. 6515-09-9, name is 2,3,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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. Safety of 2,3,6-Trichloropyridine

General procedure: For the 5-subsititution was H, F or Cl, the procedure was as follows: A mixture of compound 7 (0.79 g, 5.25 mmol), 5-substituted-2,4-dichloropyrimidine (5 mmol) and DIPEA (1.05 mL,6 mmol) in i-PrOH was heated under reflux for 6 h.Water (100 mL)was added and the solid was filtered off, washed with water and driedto obtain compounds 10a-10c. For the 5-subsititution was methyl or methoxy, the procedure was as follows: To a mixture of compound 7 (1.26 g, 8.4 mmol) and5-substituted-2,4-dichloropyrimidine (8 mmol) was added NaH (60%, 0.38 g, 9.6 mmol) in DMF (6 mL) under ice bath. Then the mixture was stirred for 24 h at room temperature.Water was added dropwise to stop the reaction. The reaction mixture was extracted withdichloromethane (20 mL x 3), and the combined organic layer waswashed with brine (15mL x 2), dried over anhydrous Na2SO4 and concentrated under vacuum to afford the crude product. The residue was purified by column chromatography to obtain compound 10d and 10e. 4.1.5.1. 2-((3,6-Dichloropyridin-2-yl)amino)benzamide (10a).Yield 80%. MP: 222-223 C.1H NMR (400 MHz, DMSO-d6) delta 12.27 (s,1H), 8.88 (d, J = 4.4 Hz, 1H), 8.55 (d, J = 8.0 Hz, 1H), 8.46 (s, 1H), 7.82(dd, J = 7.6, 0.8 Hz, 1H), 7.62-7.58 (m, 1H), 7.24-7.21 (m, 1H), 2.84(d, J = 4.8 Hz, 3H). 13C NMR (100 MHz, DMSO-d6) delta 168.70, 156.63,156.12, 155.25, 138.33, 131.84, 128.11, 123.06, 120.92, 120.77, 114.93,26.36.

With the rapid development of chemical substances, we look forward to future research findings about 6515-09-9.

Reference:
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
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.23612-36-4, name is 3-Bromo-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.032, as common compound, the synthetic route is as follows.category: pyridine-derivatives

N-BOC-3-bromo-5-azaindole[00146] Referring now to the Scheme 1 as shown in Fig. 1 , a solution of 3.5601g(18.06 mmol) of 3-bromo-5-azaindole (2) and 0.4651 g (3.8 mmol, 21 mol%) of dimethylaminopyridine (DMAP) in 80 ml. of THF was placed in a 250 ml. three-neck round-bottom flask equipped with a magnetic stirrer, thermocouple, nitrogen bleed, and cooling ice bath. A total of 4.7769g (21.88 mmol, 1.2 eq.) of BOC2O was added to the flask at 17C, and the resulting mixture was stirred until starting 3-bromo-5-azaindole disappeared, as monitored by TLC (generally, overnight stirring at room temperature). The resulting yellow solution was concentrated on rotavap, washed with 100 ml. of saturated sodium bicarbonate, and extracted with dichloromethane (3×80 ml_). The organic phase was dried over Na2SO4 and concentrated on rotavap to afford 6.57g of orange solid. This crude material was purified on CombiFlash using hexane/ethyl acetate as eluent to give 5.25g (97% yield) of n-boc-3-bromo-5-azaindole (3) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23612-36-4, 3-Bromo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ISIS INNOVATION LTD.; EBETINO, Frank, Hallock; MAZUR, Adam; LUNDY, Mark, Walden; RUSSELL, Robert, Graham, Goodwin; WO2010/33981; (2010); 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. 113209-90-8, name is (4-Chloro-5-fluoropyridin-2-yl)methanol, molecular formula is C6H5ClFNO, 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. Application In Synthesis of (4-Chloro-5-fluoropyridin-2-yl)methanol

To a solution of Intermediate 47 (200 mg) in CH2Cl2 (5 ml) was added manganese oxide (861 mg). The suspension was stirred overnight and filtered eluting with CH2Cl2. The filtrate was concentrated in vacuo to afford 130 mg (66%) of the title compound as a yellow oil. 1H-NMR (delta, ppm, CDCl3): 10.00 (s, 1 H), 8.64 (s, 1 H), 8.06 (d, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 113209-90-8.

Reference:
Patent; GLAXO GROUP LIMITED; EP2080761; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109306-86-7 , The common heterocyclic compound, 109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, 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.

2- (2-bromophenyl) pyridine(40.7 g, 174.0 mmol) was dissolved in 500 ml of anhydrous THF and cooled to -78 C. 2.5 M n-BuLi (73.2 ml, 183 mmol) was slowly added thereto and stirred for 1 hour.To this reaction solution was added 9-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] dioxin-11-one (53.0 g, 165.4 mmol) obtained in the above Step 3 The temperature was then slowly raised to room temperature and stirred for 3 hours.Aqueous ammonium chloride solution was added to terminate the reaction, distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure and then purified by column chromatography to obtain the compound 9-chloro-11- (2- (pyridin-2-yl) phenyl) -11H-indeno [ Benzo [b, e] [1,4] dioxin-11-ol (69.6 g, yield 80%).

The synthetic route of 109306-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doosan Co., Ltd; Choi Tae-jin; Kim Yeong-bae; Kim Hoe-mun; (65 pag.)KR2019/30391; (2019); A;,
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. 188577-69-7, name is 3,4-Dichloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 188577-69-7

3,4-dichloro-2-aminopyridine (500 mg, 3.07 mmol, prepared with reference to document: Synthetic Communications, 1997, 27(5), 861-870.) and 2-fluoro-4-nitrophenol (1.928 g, 12.27 mmol) were heated to 120 C. and melted, and stirred for 24 hrs. The molten was cooled to room temperature, and subjected to silica gel column chromatography (the eluent was dichloromethane to dichloromethane/methanol=50/1) for purification, to obtain a white solid (137 mg, 16%). 1H NMR (DMSO-d6, 300 MHz) delta 8.38 (dd, 1H, J=10.5, 2.4 Hz), 8.148.09 (m, 1H), 7.86 (d, 1H, J=5.4 Hz), 7.427.36 (m, 1H), 6.60 (br, 2H), 6.27 (d, 1H, J=5.4 Hz).

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, 188577-69-7, 3,4-Dichloropyridin-2-amine.

Reference:
Patent; SHANGHAI HUILUN LIFE SCIENCE & TECHNOLOGY CO., LTD; Cheng, Jianjun; Qin, Jihong; Ye, Bin; US2014/206679; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem