Category: pyridine-derivatives

Related Products of 944900-06-5, 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.944900-06-5, name is 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, molecular formula is C7H3ClF3NO, molecular weight is 209.55, as common compound, the synthetic route is as follows.

A mixture of 2-chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde 8 (19.0 g, 90.8 mmol), Ti(OEt)4 (41.4 g, 182 mmol), and (S)-(-)-tert-butylsulfinamide (11.2 g, 92.6 mmol) in THF (200 mL) was stirred at reflux for 5 h. The cooled reaction mixture was concentrated, and dissolved in AcOEt (500 mL). The resulting suspension was filtered through a Celite pad, and the filtrate was concentrated and purified by column chromatography (hexane/AcOEt = 4:1) to provide the imine (28.9 g, 99%) as a light yellow solid. 1H NMR (CDCl3) delta: 9.00 (1H, s), 8.53 (1H, d, J = 7.8 Hz), 7.73 (1H, d, J = 7.8 Hz), 1.29 (9H, s). A mixture of the imine (28.9 g, 90.0 mmol), allyl bromide (55.9 g, 0.46 mol), and indium (42.5 g, 0.37 mol) was vigorously stirred in saturated NaBr aq at room temperature for 21 h. After addition of saturated NaHCO3 aq (500 mL), the reaction mixture was extracted with AcOEt (250 mL * 3). The organic layers were filtered through a Celite pad, and dried (Na2SO4), concentrated and purified by column chromatography (hexane/AcOEt = 1:4 with 5% of Et3N) to provide 12 as a colorless solid (30.7 g, 94%). 1H NMR (CDCl3) delta: 7.95 (1H, d, J = 7.8 Hz), 7.64 (1H, d, J = 7.8 Hz), 5.79-5.68 (1H, m), 5.24 (2H, t, J = 14.1 Hz), 5.03-4.99 (1H, m), 3.78 (1H, s), 2.79-2.73 (1H, m), 2.51-2.43 (1H, m), 1.24 (9H, s).

The chemical industry reduces the impact on the environment during synthesis 944900-06-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Matsufuji, Tetsuyoshi; Shimada, Kousei; Kobayashi, Shozo; Ichikawa, Masanori; Kawamura, Asuka; Fujimoto, Teppei; Arita, Tsuyoshi; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Sogawa, Yoshitaka; Nagai, Yoko; Yoshida, Kazuhiro; Abe, Yasuyuki; Kimura, Takako; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 89 – 104;,
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.951625-93-7, name is Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7ClN2O2, molecular weight is 210.62, as common compound, the synthetic route is as follows.SDS of cas: 951625-93-7

A suspension of 1 equivalent of compound 15 and 10 equivalents of phenyl hydrazine was heated to 90 C. for 16 hours. Water was added to the reaction mixture at room temperature and decanted to remove the excess phenyl hydrazine. The crude reaction mixture was dissolved in MeOH and 0.1 N NaOH (2:1, 0.033 M) and stirred for 3.5 hours before concentrating to dryness. Purification by column chromatography afforded the title compound 16 as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 6.43-6.72 (m, 1H) 7.04-7.28 (m, 1H) 7.37-7.56 (m, 4H) 7.84-8.13 (m, 2H) 8.33-8.55 (m, 1H) 11.99 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,951625-93-7, Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Helicon Therapeutics, Inc.; US2012/95016; (2012); 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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H2BrClF3N

Step C. (1 S, 1 aS,6aR)-4-((5-(6-chloro-4-(trifluoromethyl)pyridin-3-yl)-2-fluorobenzyl)oxy)- l, la,6,6a-tetrahvdrocyclopropara1indene-l -carboxylic acid, ethyl ester 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine (974 mg, 3.74 mmol) was added to a solution of (l S,laS,6aR)-4-((2-fluoro-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)benzyl)oxy)-l, la,6,6a-tetrahydrocyclopropa[a]indene-l -carboxylic acid, ethyl ester (1.583 g, 3.5 mmol) in DME (20 ml) under N2, followed by potassium carbonate (2.43 g, 17.58 mmol) and l,l’-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (35 mg, 0.043 mmol). The mixture was heated at 90C overnight. It was poured into saturated NH4CI solution and extracted with EtOAc (lx). The organic phase was washed with brine, dried (MgS04), filtered and the solvent evaporated. The residue was purified on silica gel using hexane and to give the title compound. MS m/e: (M+H)+ 506, 508.

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, 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 188577-68-6, 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 188577-68-6, name is 4,5-Dichloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of ( 4,5-dichloropyridin-2-amine (0.1 g, 0.61 mmol) in dioxane (5 mL) was added iodobenzene (0.25 g, 1.22 mmol), cesium carbonate (0.597 g, 1.83 mmol), and Xantphos (4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; 0.035 g, 0.06 mmol). The mixture was degassed with argon for 10 min, then tris(dibenzylideneacetone)dipalladium(0) (0.029 g, 0.03 mmol) was added, and the mixture was degassed again with argon for 10 min. The mixture was stirred for 3 h at 100 C. The mixture was cooled, concentrated under reduced pressure, diluted with water (10 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by gradient column chromatography using ethyl acetate in hexane as eluent to afford 4,5-dichloro-N-phenylpyridin-2-amine as an off-white solid (82 mg, 56% yield). 1HNMR (400 MHz, CDCl3): delta 8.17 (s, 1H), 7.36 (t, J=7.2 Hz, 2H), 7.28 (s, 2H), 7.12 (t, J=7.6 Hz, 1H), 6.92 (s, 1H), 6.51 (br s, 1H). LC-MS calcd exact mass 238.01, found m/z 239.1 [M+H]+.

According to the analysis of related databases, 188577-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 823221-93-8, 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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, 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 solution of 5-bromo-2-chloro-4-trifluoromethyl-pyridine (2.54 g, 9.80 mmol) in MeOH (25 mL) was added 25% NaOMe in MeOH (3.2 ml, 14.70 mmol) and heated at reflux for 2 h. The RM was diluted with water and extracted with hexane. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure to give 5-bromo-2-methoxy-4-trifluoromethyl-pyridine(1.7 g, 68%).

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 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); 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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, the common compound, a new synthetic route is introduced below. name: N-((6-Chloropyridin-3-yl)methyl)ethanamine

General procedure: This embodiment is basically the same as Embodiment 1, except that:Step 2, using 170 g (15%) sodium carbonate instead of 52 g (40%) potassium carbonate aqueous solution, 41.8 g (98%) 2-chloro-5-ethylaminomethylpyridine instead of 40% methylamine.As a result, 70.5 g of (E)-N-(2-chloro-5-thiazolylmethyl)-N-ethyl-N’-(6-chloro-3-pyridylmethyl)-N’-ethyl-2- Nitrovinylidene diamine, content 98.1%, yield 83.1%. _: 2 In a 500 mL four-necked flask, 35.1 g (89%) of 1,1-dichloronitroethylene (0.22 mol) and 150 mL of dichloromethane were added.Stirring was carried out to 0 to 10 C, and 36.2 g (98%) of 2-chloro-5-ethylaminomethylthiazole (0.2 mol) was added dropwise. After the addition, 52 g (40%) of potassium carbonate aqueous solution was added dropwise at this temperature. , keep warm for 2 hours,Sampling HPLC analysis of N-(2-chloro-5-thiazole) methyl-N-ethylamine conversion rate of 98% or more, adding 38.8g (40%) methylamine aqueous solution (0.5mol) at 5-10 C, plus Stir for 1 hour after finishing.The temperature was raised to 20 to 25 C for 2 hours, and the oil layer was separated and allowed to stand, and the aqueous layer was extracted with dichloromethane for 3 times.The oil layer was desolvated, and 70 g of ethyl acetate was added to the residue, stirred well, and cooled to 0 to 5 C for filtration.Drying to obtain 50 g of (E)-N-(2-chloro-5-thiazolylmethyl)-N-ethyl-N’-methyl-2-nitrovinylidene diamine, content 98%, yield 88.6% .

The synthetic route of 120739-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lianyungang Liben Crop Technology Co., Ltd.; Wu Hailin; Dong Junjie; Dai Zhanyong; Gong Jian; Li Datie; (6 pag.)CN107474022; (2017); A;,
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.65169-42-8, name is Methyl 6-chloro-5-methylnicotinate, molecular formula is C8H8ClNO2, molecular weight is 185.6076, as common compound, the synthetic route is as follows.Product Details of 65169-42-8

To a suspension of methyl 6-chloro-5-methyl-nicotinate (467 mg) in carbon tetrachloride (25 mL) were added N-bromosuccinimide (1.34 g) and benzoyl peroxide (218 mg), and the mixture was stirred at 100C for 7.5 hours. The mixture was cooled to room temperature, and to the reaction mixture were added saturated aqueous sodium thiosulfate solution and water, and the reaction mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtrated, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (833 mg). LC-MS, condition B ([M+H]+/Rt (min)): 341.9/1.011

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65169-42-8, Methyl 6-chloro-5-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Dainippon Pharma Co., Ltd.; FUKUNAGA, Yuichi; YAMAKAWA, Erina; SUGARU, Eiji; IKEDA, Satoshi; OTSUBO, Tsuguteru; UMEHARA, Hiroki; LI, Chiang Jia; (87 pag.)EP3560494; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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, Product Details of 161117-83-5, blongs to pyridine-derivatives compound. Product Details of 161117-83-5

Ketone 2-1 To a -70 C. solution of 1.12 g (5.0 mmol) of 3-(N-tertbutoxycarbonylamino)-2-methoxypyridine (Kelly, Tetrahedron Lett. 35 (48), 1994, 9003-9006) in 25 ML of dry ether was added 1.8 ML (12.0 mmol) TMEDA followed by 4.8 ML (12.0 mmol) of n-BuLi. The resulting solution was warmed to -15 C. where it was aged for 2 h.. The reaction mixture was recooled to -70 C. and treated with 0.83 ML (7.0 mmol) of ethyl trifluoroacetate.. After stirring an additional 3 h, the reaction was quenched with 25 ML of saturated NH4Cl solution and the two phases were separated.. The aqueous phase was extracted with 100 ML of EtOAc and the combined organic extracts were washed with 25 ML of brine and dried over MgSO4.. The yellow solution was concentrated and chromatographed (CH2Cl2) to afford trifluoromethyl ketone 2-1. 1H NMR (CDCl3) delta7.95 (d, J=8 Hz, 1H), 7.10 (bs, 1H), 6.95 (d, J=8Hz, 1H), 4.05 (s, 3H), 1.50 (s, 9H).

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6350745; (2002); B1;,
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.695-98-7, name is 2,3,5-Trimethylpyridine, molecular formula is C8H11N, molecular weight is 121.1796, as common compound, the synthetic route is as follows.SDS of cas: 695-98-7

In dichloromethane (15.0 ml), 2,3,5-trimethyl-pyridine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (1.29 g) was dissolved. After having been cooled to 0 C, the reaction solution was added with m-chloroperbenzoic acid (2.53 g), followed by stirring at room temperature for 1.5 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. Subsequently, the organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resultant residue in dichloromethane (25.0 ml) . The reaction solution was added with trifluoroacetic anhydride (2.8 ml) and the whole was refluxed under heating for 3.5 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off. The resultant residue was dissolved in methanol (60.0 ml). After having been cooled to 0C, the reaction solution was added with a 12.5% sodiummethoxide/methanol solution to adj ust the solution to pH 10, and the whole was stirred at room temperature for 16.5 hours. After the solvent was distilled off, the residue was added with distilled water and subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the residue in chloroform (30.0 ml). The reaction solution was added with manganese dioxide (chemically processed product) (6.10 g) and then stirred at room temperature for 18 hours. The reaction solution was filtrated through Celite. The solvent in the filtrate was distilled off and the resultant residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.14 g) as a yellow oily substance. MS(FAB,Pos.):m/z=136[M+H]+ 1H-NMR(500MHz,CDCl3):delta=2.40(3H,s), 2.63(3H,s), 7.43(1H,brs), 8.48(1H,brs),10.16(1H,s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,695-98-7, 2,3,5-Trimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1160791-13-8, 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 1160791-13-8, name is 2-Amino-6-bromothiazolo[5,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To 6-bromothiazoio[5,4-b]pyridin-2-amine (1 .1 g, 4.8 mmol) in acetonitriie (92 mL) was added copper(ll)chloride (964 mg, 7.2 mmol) and the mixture was cooled to OX. Tert- butyl nitrite (739 mg, 7.2 mmol) in acetonitriie (46 mL) was added slowly and the mixture was stirred for 30 minutes at Omicron’ and addit ional 4 hours at room temperature. The mixture was diluted with ethyl acetate, washed with saturated NH4CI-solution, with saturated sodium bicarbonate solution, brine and water. Evaporation yielded 580 mg (47 %) 6-bromo-2-chlorothiazolo[5,4-b]pyridine NMR (300 MHz, DMSO-cfe) delta = 7.87 (d, 1 H), 8.36 (d, 1 H) ppm.

According to the analysis of related databases, 1160791-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHN, Ulrike; SCHMITT-WILLICH, Heribert; HEINRICH, Tobias; BERGER, Markus; FITZNER, Ansgar; KRAUSE, Sabine; BROCKSCHNIEDER, Damian; DYRKS, Thomas; THIELE, Andrea; MOeNNING, Ursula; BOeMER, Ulf; WO2012/7510; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem