Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, 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, Safety of 2-Bromo-5-hydroxy-3-methylpyridine, blongs to pyridine-derivatives compound. Safety of 2-Bromo-5-hydroxy-3-methylpyridine

0.49 g (6.82 mmoi) cyclopropane methanol in 10 mL THF are charged with 0.42 g (11.4 mmoi) NaH and the reaction mixture is stirred at r.t. for 20 min. Then 1.00 g (5.68 mmoi) 5-bromo-2-fluoropyridine are added and the mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, dried over MgS04l filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (MeOH/H20/FA). CgH-ioBrNO (M= 228.1 g/mol) ESI-MS: 228/229 [M+H]+ Rt (HPLC):1.14 min (method C) The following compounds are prepared analogously to example XXV.1 ; For example XXV.4 the reaction conditions are 50 C for 4 h. For examples XXV.10 – XXV.13 and XXV.19 – XXV.21 the reaction time is 2 h. For example XXV.9 no solvent is used and the reaction temperature is 95 C. For the examples XXV.4, XXV.10 – XXV.12, XXV.15 – XXV.16 and XXV.19 – XXV.21 the reaction is done in DMF. For example XXV.18 the reaction is done in DMSO at 100 C. For example XXV.21 toluene is used as solvent and the reaction conditions are 50 C for 1 h. For example XXV.22 methyltetrahydrofurane is used as solvent at 0 C for the deprotonation and 50 C for the substitution..

The synthetic route of 1003711-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); 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. 58553-48-3, name is 5-(Hydroxymethyl)picolinonitrile, molecular formula is C7H6N2O, 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. Formula: C7H6N2O

Example 3A; 5-Formyl-2-pyridinecarbonitrile 1.04 g (8. 2 mmol) oxalylchloride are dissolved in 8 ml dichloromethane. At-78C, 1.28 g (16.4 mmol) dimethylsulfoxide are added dropwise. The solution is stirred at-78C for 20 minutes, then 1 g (7.46 mmol) of the compound of Example 2A, dissolved in 7 ml dichloromethane, is added, and stirring at-78C is continued for another 2 hours. 3.4 g (33.6 mmol) triethylamine are then added dropwise, and after warming up to room temperature, the mixture is purified by column chromatography (silica, eluent: cyclohexane to cyclohexane/ethyl acetate 2: 1). Yield: 0.76 g (77% of th.) Mp.: 80-82C HPLC (method 4): Rt = 2.13 min MS (ESIpos): m/z = 133 (M+H) + ‘H-NMR (400 MHz, DMSO-d6) : 8 = 10. 18 (s, 1H), 9.21 (m, 1H), 8.49 (m, 1H), 8.27 (m, 1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 58553-48-3.

Reference:
Patent; BAYER HEALTHCARE AG; WO2005/82863; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

To a stirred solution of (2S)-2-methylpiperazine (0.30 g, 2.1 mmol) in DMA (6 mL), 6-chloropyridine-3-carbonitrile (0.29 g, 2.3 mmol) and K2C03 were added. The resultantreaction mixture was heated to 60 C for 2 h (TLC indicated complete consumption ofstarting material). The reaction mixture was diluted with cold water (20 mL) and extractedwith EtOAc (3 x 25 mL). The combined organic extracts were washed with cold water (20mL) and brine (2 x 20 mL). The organic layer was separated, dried over Na2S04 andconcentrated under reduced pressure to give the crude residue which was purified by columnchromatography (100-200 silica gel, 10 g, 10% MeOH-DCM) to furnish 6-[(3S)-3-methylpiperazin-1-yl]pyridine-3-carbonitrile (0.29 g, 67%) as an off-white solid.LCMS: m/z: 203.4 [M+Ht.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1000339-23-0, name is 2-Amino-5-bromoisonicotinic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C6H5BrN2O2

A mixture of compound 14-2 (7.81 g, 35.6 mmol), DPPA (9.40 mL, 43.5 mmol) and Et3N (5.90 mL, 42.5 mmol) in i-BuOH (300 mL) was stirred at 90 C for 6 hrs under an atmosphere of N2. The solvent was removed and the residue was purified by silica gel column chromatography (Petroleum ether/EtOAc = 5/1 to 4/1 (v/v)) to give compound 14-3 (4.9 g, 47% yield) as a white solid. LC-MS (ESI): m/z 234 [M-56+H]+.

The synthetic route of 1000339-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDIO PHARMACEUTICALS, INC.; ZHONG, Min; LI, Leping; WO2012/58125; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine, the common compound, a new synthetic route is introduced below. Quality Control of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

Step b) 1H-Pyrazolo[3,4-b]pyridine-3-carbonitrile In 33% strength aqueous ammonia solution (10 ml), 3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (500 mg, 2.67 mmol) is heated in the microwave at 140 C. for 10 min. The mixture is then concentrated under reduced pressure, and the residue is triturated at 70 C. with 100 ml of ethyl acetate and 20 ml of tert-butyl methyl ether. Insoluble components are filtered off with suction in the heat, and the filtrate is concentrated. Drying gives 346 mg (90% of theory) of the title compound as light-beige crystals. 1H-NMR (400 MHz, DMSO-d6): delta=7.47 (dd, J=8.2, 4.5 Hz, 1H), 8.46 (dd, J=8.2, 1.5 Hz, 1H), 8.73 (dd, J=4.5, 1.5 Hz, 1H), 15.02 (br. s, 1H).

The synthetic route of 956010-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/4235; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58539-65-4 , The common heterocyclic compound, 58539-65-4, name is 2-Methylnicotinamide, molecular formula is C7H8N2O, 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.

[0621] A mixture of XI-2 (13 g, 95.6 mmol, 1 eq) and 18.2 mL of N,N-dimethylformamide dimethyl acetal was heated at 50 C. for 2 hrs. During the second hour, all the volatiles was removed. The residue was cooled to rt., diluted with 100 mL of anhydrous N,N-dimethylformamide, and then treated carefully with batch wise portions of sodium hydride (5 g, 124.3 mmol, 1.3 eq, 60% oil dispersion; caution: vigorous evolution of hydrogen). The mixture was heated at 80 C. for 2.5 hrs, and then ice-cooled, treated cautiously with 25 mL of 2-propanol, and then maintained at 0-5 C. overnight. The solid were collected, and then dissolved in 10 mL of hot water. The solution was filtered, the filtrate was ice-cooled and then treated dropwise with concentrated hydrochloric acid to pH=7.0. After storage at 0-5 C. for 3 hrs, the precipitated solids were collected, washed with ice-cold water, and dried in vacuum to give XI-3 (3 g, 32% yield). 1H NMR (DMSO-d6, 300 MHz): delta 8.90 (s, 1H), 8.49 (d, J=7.6 Hz, 1H), 7.51-7.43 (m, 2H), 6.61 (d, J=7.6 Hz, 1H).

The synthetic route of 58539-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 117846-58-9, 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.117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, molecular weight is 264.95, as common compound, the synthetic route is as follows.

To a stirred anhydrous THF solution of 4 (3.22 g,12.15 mmol) was added dropwise a 2.4 mol L-1 n-BuLi inhexane solution (5.57 mL, 13.37 mmol) at 195 K under argonatmosphere. Stirring continued for 0.5 h at 195 K; a solutionof (2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene(4.90 g, 13.37 mmol) in THF was added and the reactionmixture was stirred for 1 h at this temperature. The reactionwas quenched by addition of water. After being extractedwith dichloromethane, the organic layer was washed withwater, and dried over anhydrous Na2SO4. The crude productwas purified by column chromatography on Al2O3 usingpetroleum ether as eluent to afford 6 (1.96 g, 28%) as a whitesolid. m.p. 86-87 C; 1H NMR (400 MHz, CDCl3) d 1.83(s, 3H, -CH3), 2.00 (s, 3H, -CH3), 2.29 (s, 3H, -CH3), 7.10(s, 1H, thiophene-H), 7.25 (t, 2H, J 8.0 Hz, benzene-H), 7.33 (t, 2H, J 8.0 Hz, benzene-H, pyridine-H), 7.48 (d, 2H,J 4.0 Hz, benzene-H).

The chemical industry reduces the impact on the environment during synthesis 117846-58-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Liao, Guanming; Xue, Dandan; Zheng, Chunhong; Wang, Renjie; Pu, Shouzhi; Journal of the Brazilian Chemical Society; vol. 27; 11; (2016); p. 1989 – 1997;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1079179-12-6, 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. 1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 2-chloro-3-fluoro-5-nitropyridine (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) under nitrogen atmosphere were added tributylvinyl tin (3.42 g, 10.8 mmol), Pd2(dba)3 (0.42 g, 0.45 mmol) and trifuryl phosphene (0.2 g, 0.9 mmol). The reaction mixture was deoxygenated thoroughly and was heated to 60 C for 6 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulphate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5 % ethyl acetate in n-hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine (1.5 g, 96 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; WO2013/13815; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131747-55-2 ,Some common heterocyclic compound, 131747-55-2, molecular formula is C6H6FNO, 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 a 50 ml, three-necked flask fitted with a magnetic stirrer under inert atmosphere,5-chloro-1 H-indole x70 (1.13 g, 7.43 mmol) is dissolved in dry DMF (20 ml). At 00C, NaH(327 mg, 8.18 mmol, 60 % in mineral oil) is added and the mixture is stirred at this temperature for 0.3 h. A solution of 3-(chloromethyl)-2-fluoropyridine x71 (obtained from (2-fluoropyridin-3-yl)methanol and SOCI2 (1.3 g, 8.92 mmol)) in DMF (5 ml) is then added and stirring is continued for 0.5 h at 0 0C. The reaction mixture is poured on ice and the aqueous phase is extracted three times with AcOEt. The combined organic phases are dried over MgSOphi filtered and concentrated. Purification by chromatography on silicagel(Hexane/AcOEt: 9/1 (v/v)) affords 5-chloro-1-[(2-fluoropyridin-3-yl)methyl]-1 H-indole x72 as a solid (1.13 g).Yield: 59 %.1H NMR (250 MHz, DMSO): 5.5 (s, 2H), 6.5 (s,1H), 7.1 (dd, 1H), 7.3 (m, 1 H), 7.4- 7.6 (m, 3H), 7.6 (d, 1H), 8.1 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131747-55-2, its application will become more common.

Reference:
Patent; UCB S.A.; WO2006/128692; (2006); 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. 1796-84-5, name is 4-Ethoxy-3-nitropyridine, molecular formula is C7H8N2O3, 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. name: 4-Ethoxy-3-nitropyridine

Example 6 Preparation of 2-amino-4-ethoxy-5-nitropyridine: 2-Amino-4-ethoxy-5-nitropyridine with a melting point of 215 to 217 C. is obtained from 0.34 g of 4-ethoxy-3-nitropyridine, 0.33 g of N,N-tetramethylenethiocarbamoylsulphenamide and 0.6 g of potassium tert.-butylate following the same procedure as in Example 2; the yield is 0.28 g (75%).

With the rapid development of chemical substances, we look forward to future research findings about 1796-84-5.

Reference:
Patent; Bayer Aktiengesellschaft; US5262539; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem