Category: pyridine-derivatives

Reference of 106047-28-3, 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 106047-28-3 as follows.

Step 2 1-methyl-4-nitro-2-[2-(3-pyridyl)pyridin-6-ylamino]benzene This compound was prepared by version of the method described in the document (J. Org. Chem., 2000, 65, 1144-1157.). To 940 mg of 2-bromo-6-(3-pyridyl)pyridine obtained in the step 1, 730 mg of 2-methyl-5-nitroaniline, 37 mg of tris(dibenzylideneacetone)dipalladium (0), 75 mg of (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(+-)-BINAP] and 1.82 mg of cesium carbonate, 12 ml of toluene was added and the mixture was stirred with heating at 110C for 24 hours under an argon atmosphere. After air cooling, the reaction solution was diluted with ethyl acetate and insolubles were removed by filtration. The solvent in the filtrate was distilled off under reduced pressure and the residue was crystallized by adding diethyl ether. The resulting crystal was collected by filtration and then washed with ethyl acetate-diethyl ether to obtain 646 mg of the objective compound as a yellow crystal. Melting point: 148-150C 1H-NMR(CDCl3)delta: 2.42(3H, s), 6.53(1H, br), 6.80(1H, d), 7.35(2H, d), 7.44(1H, dd), 7.69(1H, m), 7.83(1H, dd), 8.44(1H, dt), 8.65(1H, dd), 9.09(1H, d), 9.20(1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,106047-28-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1533304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, 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 tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, blongs to pyridine-derivatives compound. Safety of tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

[00316] fer -Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0. 3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2S03 (1.5 eq) was added via addition funnel. After completion of Na2S03 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2C03 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3- methylpyridine-1 -oxide (95%) that was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SWINNEY, Kelly, Ann; HURTER, Patricia, Nell; NADIG, David, E.; SMITH, David; THOMAS, Vance, Hayden; WARMAN, Martin, Paul; WO2015/73231; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175204-80-5 , The common heterocyclic compound, 175204-80-5, name is 3-Amino-4-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, 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.

Preparation III; 4-(Trifluoromethyl)-3-pyridinol; A solution of 2 g (12.34 mmol) of 3-amino-4-(trifluoromethyl)pyridine in 28 ml of 50% sulfuric acid is cooled to -5 C. and a solution of 1.03 g (14.8 mmol) of sodium nitrite in 10 ml of water is added slowly. The mixture is left to return to room temperature and stirring is continued for 30 min. 25 ml of concentrated sulfuric acid are then added and the reaction mixture is stirred at 100-110 C. for 2 hours. After cooling, the reaction medium is neutralized by adding saturated sodium bicarbonate solution to pH 6-7, and the mixture is extracted with ethyl acetate. The organic phase obtained is washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 1.92 g of the expected compound in the form of a brown powder (yield=95%). M.p.=112-114 C.

The synthetic route of 175204-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratoires Fournier S.A.; US2007/54955; (2007); 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. 77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, 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: C8H8BrNO2

Under the protection of N2, m-chloroperoxybenzoic acid (36.00g, 0.208 mol) was added to an ethyl acetate (126 mL) solution of ethyl 5-bromopyridine-2-carboxylate (15.00g, 0.065 mol), and the resulting mixture was heated to 70C to react overnight. After cooling, water was added. The resulting mixture was extracted with ethyl acetate, washed with a saturated sodium sulfite aqueous solution, washed with a saturated sodium carbonate aqueous solution, dried with anhydrous sodium sulfate, and concentrated. The residue was separated through a silica gel column (ethyl acetate:petroleum ether=1:5) to obtain a yellow product (6.60 g, 41%). 1H NMR (400 MHz, CDCl3,) delta 8.42 (d, 1H), 7.53 (d, 1H), 7.41-7.43 (m, 1H), 4.44-4.50 (q, 2H), 1.42 (t, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 77199-09-8.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); 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. 1721-23-9, name is 3-Cyano-2-methylpyridine, molecular formula is C7H6N2, 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 3-Cyano-2-methylpyridine

Step 3 Preparation of 2-methyl-3-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine: To a suspension of 4-(methylsulfonyl)aniline hydrochloride (6.85 g, 0.040 mol) in dichloroethane (400 mL) was added triethylaluminum (1.9M solution in toluene, 32.0 mL, 60 mmol) over 15 minutes at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 hours. A solution of 3-cyano-2-methylpyridine, from step 2, in 70 mL of dichloroethane was added over 10 minutes and the mixture was stirred at 75 C. for 16 hours. The reaction mixture was cooled to room temperature and treated with 50 g of silica gel. The mixture was stirred for 30 minutes and filtered. The filtrate and washings were concentrated under reduced pressure and the residue was washed with ether to give 7.3 g of crude 2-methyl-N-[4-(methylsulfonyl)phenyl]-3-pyridinecarboximidamide (60%). To a mixture of the above crude amidine (7.0 g, 0.024 mol) and sodium bicarbonate (4;0 g, 0.048 mol) in isopropanol (350 mL) was added 3-bromo-1,1,1-trifluoroacetone (6.9 g, 0.036 mol) rapidly at room temperature. After heating the reaction mixture at 75-80 C. for 16 hours, the solvent was removed and the residue was partitioned between water and methylene chloride. The organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (ethyl acetate/acetone, 98:2) to give 4.02 g of pure 2-methyl-3-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine as a yellow solid (25%): mp (DSC) 237-239 C. Anal. Calc’d. for C17 H16 F3 N3 O3 S: C, 51.12, H, 4.04, N, 10.52, S, 8.03. Found: C, 50.92, H, 4.12, N, 10.04, S, 7.83.

With the rapid development of chemical substances, we look forward to future research findings about 1721-23-9.

Reference:
Patent; GD Searle & Co; US5616601; (1997); 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. 6623-21-8, name is 4,6-Dimethylnicotinonitrile. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

4,6-Dimethylnicotinonitrile (1.0 g, 7.6 mmol) was dissolved in ethanol (35 mL) and the mixture was treated with Raney nickel (5 mL, slurry in water) and hydrazine hydrate (3.8 mL, 75.6 mmol). The solution was stirred overnight at room temperature. Compound 2a was obtained by filtering the reaction mixture through a pad of diatomaceous earth, which was rinsed with methanol (3*50 mL). The filtrate was dried over Na2SO4, filtered and concentrated under reduced pressure to afford Compound 2a. The compound was used without additional purification. M+ (ES+)=137.1 1H NMR (DMSO, d6) delta 2.35 (s, 3H), 2.42 (s, 3H), 4.01 (s, 2H), 7.13 (s, 1H), 8.42 (s, 1H).

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, 6623-21-8, 4,6-Dimethylnicotinonitrile.

Reference:
Patent; Coats, Steven J.; Dyatkin, Alexey B.; He, Wei; Lisko, Joseph; Miskowski, Tamara; Ralbovsky, Janet L.; Schulz, Mark; US2008/269225; (2008); 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. 192447-58-8, name is 2,6-Dibromo-N,N-dimethylpyridin-4-amine. A new synthetic method of this compound is introduced below., COA of Formula: C7H8Br2N2

(3) Production of 2-bromo-4-dimethylamino-6-{3-(trifluoromethyl)phenoxy} pyridine as an intermediate product 1.4 g (0.0071*1.2 mol) of 3-(trifluoromethyl) phenol was dissolved in about 20 ml of dimethyl formamide. The solution was further mixed with 0.30 g (ca. 60% in mineral oil; 0.0071*1.06 mol) of sodium hydride and then with 2.00 g (0.0071 mol) of 2,6-dibromo-4-dimethylamino pyridine. After treating the solution under reflux for about 6 hours, the solution was allowed to stand for cooling to room temperature. After the reaction solution was distributed with hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate, followed by concentration thereof. Thereafter, the concentrated solution was purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane) and the obtained product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield by weight: 1.67 g; yield by percentage: 65%; solid; melting point: 61 to 66 C.; 1 H-NMR (60 MHz, CDCl3, delta): 2.86 (6H, s), 6.88 (1H, d, J=2 Hz), 6.38 (1H, d, J=2 Hz), 6.9-7.5 (4H, complex).

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, 192447-58-8, 2,6-Dibromo-N,N-dimethylpyridin-4-amine.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6005112; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1190319-62-0, 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.1190319-62-0, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, molecular formula is C7H5BrN2O, molecular weight is 213.03, as common compound, the synthetic route is as follows.

Pottasium tert-butoxide (0.03 g, 0.27 mmol) was added to a suspension of 6-bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (preparation 16c, 0.87 g, 4.1 mmol) in dimethylsulphoxide (4 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45 C and methyl acrylate (1.14 mL, 12.71 mmol) was added dropwise over 60 minutes. After the addition, the mixture was stirred for 2 hours and then further potassium tert-butoxide (1.4 g, 12.21 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 2 hours. Water (20 mL) was added and heating was continued at 85 C for 2 hours and then the mixture was left to cool overnight. Ethyl acetate was added and the organic layer was washed with water, brine, dried (MgSO4) and evaporated to give the title compound (0.60 g, 50%) as a white solid. LRMS (m/z): 293/295 (M-1)+. 1H-NMR delta (CDCl3): 2.14 (m, 2H), 2.27 (m, 2H), 2.73 (m, 2H), 3.01 (m, 2H), 7.40 (d, J=1.5 Hz, 1H), 8.29 (d, J=1.5 Hz, 1H), 8.44 (br s, 1H).

The chemical industry reduces the impact on the environment during synthesis 1190319-62-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63572-73-6, 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 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

4N NaOH (5.12 mL, 20.5 mmol) was added to a cold (O0C) solution of 5-nitro-lH-pyrazolo[3,4-b]pyridine (0.84 g, 5.12 mmol) in dioxane (30 mL), followed by bromine (1.05 mL, 20.5 mmol). The cold bath was removed, and the reaction mixture was left at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and quenched with saturated Na2S2O3 (50 mL). The aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (9:1) to give 3-bromo-5-nitro-lH-pyrazolo[3,4-b]pyridine (1.10 g, 88%) as a solid.

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 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; AHRENDT, Kateri A.; BUCKMELTER, Alexandre J.; DE MEESE, Jason; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen R.; LUNGHOFER, Paul; MORENO, David; NEWHOUSE, Brad; REN, Li; SEO, Jeongbeob; TIAN, Hongqi; WENGLOWSKY, Steven Mark; FENG, Bainian; GUNZNER, Janet; MALESKY, Kim; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; YOUNG, Wendy B.; WO2009/111279; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 59782-88-6, name is 2,5-Dichloro-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 59782-88-6

EXAMPLE 15 Under the conditions of Example 3(a), 2-(8-chloro-6-methyl-11-oxo-11H-pyrido[2,1-b]quinazolin-2-yl)propionic acid, m.p. 226 (dimethylformamide-water), is obtained from 2,5-dichloro-3-methylpyridine and 2-(4-amino-3-carboxyphenyl)propionic acid.

With the rapid development of chemical substances, we look forward to future research findings about 59782-88-6.

Reference:
Patent; Schering, Aktiengesellschaft; US4457927; (1984); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem