Category: pyridine-derivatives

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. 6295-87-0, name is 1-Aminopyridinium Iodide. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H7IN2

General procedure: Potassium carbonate (9.0 mmol) for 3a-t or triethylamine (9.0 mmol) for 3u was added to a solution of 1-aminopyridinium iodide 1 (3.0 mmol) in acetonitrile (25 mL) for 3a-t or EtOH (25 mL) for 3u. The reaction mixtures were stirred vigorously for 10-20 min at room temperature to give a dark purple solution, to which electrophiles 2a-u (3.0 mmol) were added in one portion. The mixtures were stirred at rt for 3-24 h except for 3e, which was heated under reflux for 5h. Mixtures 3a-t were filtered to remove inorganic salts, which were washed with acetonitrile 3-5 times. The combined filtrates were concentrated in vacuo and the residues were purified either by gradient elution chromatography over silica gel and/or by recrystallization.

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, 6295-87-0, 1-Aminopyridinium Iodide.

Reference:
Article; Zhang, Hong; Wang, Zuoquan; Jabeen, Farukh; Gopinathan-Pillai, Girinath; Zhou, Wenfeng; Steel, Peter J.; Hall, C. Dennis; Katritzky, Alan R.; Tetrahedron Letters; vol. 57; 1; (2016); p. 20 – 24;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16135-36-7, 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.16135-36-7, name is Methyl 4-aminonicotinate, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.

4- [2-(5-Chloro-2-fluoro-phenyl)-7-(2-dimethylamino-ethylamino)-pyrido [2,3-d] – pyrimidin-4-ylamino] -nicotinic acid methyl ester. Crude imino halide, N’-[4-Chloro-2-(5-chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidin-7-yl]-N,N- dimethyl-ethane-l,2-diamine (0.58 g) dissolved in dioxane (80ml) was added Pd(OAc)2 (0.077 g) followed by BINAP (0.115 g), 4-amino-pyridyl-3-carboxylate (0.232 g) and Cs2CO3 (0.748 g). The reaction mixture was heated to 8O0C for 15h. The reaction mixture was cooled to r.t. and filtered through Celite and the crude material was purified by silica gel flash column chromatography (3:2/ethyl acetate:hexane) to give 4-[2-(5-Chloro-2-fluoro-phenyl)-7-(2-dimethylamino-ethylamino)-pyrido[2,3-d]- pyrimidin-4-ylamino] -nicotinic acid methyl ester (0.300 g).

The chemical industry reduces the impact on the environment during synthesis 16135-36-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/100310; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1150617-54-1 , The common heterocyclic compound, 1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine, molecular formula is C6H4BrN3, 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.

A solution of 6-bromo-lH-pyrazolo[4,3-]pyridine (500 mg, 2.52 mmol) and cesium carbonate (1234.04 mg, 3.79 mmol) in DMF (7.5 mL) was stirred at r.t. lodomethane (189 mu, 3.03 mmol) was added and the reaction mixture was stirred for 1.5 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between water (25 mL) and EtOAc (25 mL). The aqueous phase was further extracted with EtOAc (25 mL). The combined organic phase was washed with brine (25 mL), then dried over MgS04 and filtered. The solvent was removed in vacuo to give the title compounds (584.8 mg) as a 7:3 mixture of regioisomers, which was used in the next step without further separation. Method B HPLC-MS: MH+ mlz 212/214, RT 1.47 minutes (26%) and 1.56 minutes (72%)

The synthetic route of 1150617-54-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52568-28-2, 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 52568-28-2, name is 2-(Pyridin-2-yl)propan-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of the acid (1 equiv.) in DCM (0.2 M) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.), DIPEA (1.2 equiv.) at 0 C. After the mixture was stirred for 10 min, the amine (1.2 equiv.) was added. The reaction was stirred overnight at room temperature. Then water was added and the mixture was extracted with DCM. The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography on silica gel to give the desired product.

According to the analysis of related databases, 52568-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Haifeng; Niu, Youhong; Zhang, Guoying; Ye, Xin-Shan; Tetrahedron Letters; vol. 57; 41; (2016); p. 4544 – 4548;,
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 153034-90-3, name is 2-Chloro-4-iodonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H3ClINO

The following compounds were dissolved in a mixed solution of 200 ml of toluene, 100 ml of ethanol, and 100 ml of a 2-normal aqueous sodium carbonate solution.Compound 1-1: 3.83 g (14.3 mmol)Compound 4-4: 4.0 g (12.9 mmol)While the resulting reaction solution was stirred at a room temperature in a nitrogen atmosphere, 0.83 g (0.72 mmol) of tetrakis(triphenylphosphine)palladium(0) was added in the reacting solution. The reaction solution was heated to 60 degrees Celsius and then stuffed for 7 hours. After the reaction was completed, water was added to the reaction solution. The organic layer was extracted with toluene and dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (gel used in chromatography: BW300 (produced by Fuji Silysia Chemical Ltd.), developing solvent:ethyl acetate/heptane = 1/2) and washed with methanol. Thus, 1.6 g (yield 38%) of Compound 4-5 was prepared.

With the rapid development of chemical substances, we look forward to future research findings about 153034-90-3.

Reference:
Patent; CANON KABUSHIKI KAISHA; ABE, Shigemoto; KAMATANI, Jun; KISHINO, Kengo; SAITOH, Akihito; YAMADA, Naoki; KOSUGE, Tetsuya; HORIUCHI, Takayuki; NISHIDE, Yosuke; MIYASHITA, Hirokazu; WO2014/115528; (2014); 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 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. This compound has unique chemical properties. The synthetic route is as follows. name: N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine

Embodiment 2 In a 5000 ml dried 4-neck flask, 3000 ml dichloromethane,277 g 4-methyl-N-3-(4-pyridin-3-yl-pyrimidin-2-yl)-1,3-benzenediamine, and 270 g 4-(4-methyl-piperazin-1-methyl)-benzoic acid ethyl ester were added. After it was stirred to dissolve, 100 g sodium methoxide was then added. The mixture was heated to 40 C. for reflux and reaction overnight until the reaction was detected to be complete, and then was concentrated to remove toluene. The residue solid was washed with water and dried, thus 455 g Imatinib was obtained, and the yield was 92.0%. The data of spectrum is the same as above.

With the rapid development of chemical substances, we look forward to future research findings about 152460-10-1.

Reference:
Patent; Shen, Xin; He, Xiao; Yang, Jidong; Wu, Shaohong; Zhan, Huaxing; US2013/41149; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 117007-52-0 , The common heterocyclic compound, 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine, molecular formula is C6H4IN3, 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.

Compound (M-2) was dissolved in THF (8.4 mL)TEA (234 muL, 1.68 mmol),(Boc) 2 O (289 muL, 1.26 mmol) and DMAP(10.3 mg, 0.0839 mmol) were sequentially added,And the mixture was stirred at room temperature for 1 hour.Water was added to the reaction solution, and the mixture was extracted with ethyl acetate.The organic layer was washed with water,And then washed successively with saturated brine,After drying with anhydrous sodium sulfate, filtration was carried out.After distilling off the solvent under reduced pressure,The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate)Compound (VII-10)(Yield 151 mg, Yield 52%)As a white solid.

The synthetic route of 117007-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; Watanabe, Atsushi; Sato, Yuki; ogura, Keiji Tamada; Tatsumi, Yoshiyuki; (283 pag.)JP2018/145180; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6188-23-4 ,Some common heterocyclic compound, 6188-23-4, molecular formula is C7H5BrN2, 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.

Example 896-(lmidazo[1,2-a]pyridin-6-ylethynyl)-2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)- one [00270] A mixture of 6-bromoimidazo[1 ,2-a]pyridine (4.00 g, 20.30 mmol), ethynyltrimethylsilane (2.98 g, 30.30 mmol), PdCI2[PPh3]2 (460 mg, 0.66 mmol), Cul (380 mg, 2.02 mmol), and TEA (8.4 mL, 60.9 mmol) in benzene (25 mL) is stirred at 50 C under argon atmosphere for 8 h, cooled down to r.t. and concentrated at reduced pressure. The obtained residue is purified by column chromatography (silica gel, EtOAc/hexane) to give 6-((trimethylsilyl)ethynyl)imidazo[1 ,2-a]pyridine (3.20 g, 74%) as yellow solid.[00271 ]TBAF solution in THF (1 M, 1 .04 mL, 1 .04 mmol) is added dropwise to a solution of 6-((trimethylsilyl)ethynyl)imidazo[1 ,2-a]pyridine (3.20 g, 14.90 mmol) in THF (20 mL) at 0 C. The resulting mixture is stirred at 0 C for 1 h, diluted with water and extracted with DCM (3×30 mL). The combined organic phases were dried over Na2S04 and concentrated at reduced pressure. The obtained residue was purified by column chromatography (silica gel, EtOAc/hexane) to give 6-ethynylimidazo[1 ,2-a]pyridine (1 .37 g, 65%) as brown oil.[00272]According to General Procedure 1 , 6-bromo-2,2-dimethyl-2/-/-pyrano[2,3- b]pyridin-4(3/-/)-one (256 mg, 1 .0 mmol) is reacted with 6-ethynylimidazo[1 ,2-a]pyridine (156 mg, 1 .1 mmol) in the presence of PdCI2[PPh3]2 (35 mg, 0.05 mmol), P(f-Bu)3 (10 mg, 0.05 mmol), DBU (15 mg, 0.1 mmol), and TEA (2 mL) in acetonitrile (10 mL) at reflux for 6 h. The crude product is purified by column chromatography (silica gel, EtOAc/hexane) to provide the title compound (123 mg, 39%).1H NMR (De-DMSO), deltaEta, 1 .47 (s, 6H), 2.92 (s, 2H), 7.32 (d, 1 H), 7.60 (d, 1 H), 7.64 (s, 1 H), 7.96 (s, 1 H), 8.24 (s, 1 H), 8.66 (s, 1 H), 8.92 (s, 1 H).LC/MS (M+H)+ = 318

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; ABEL, Ulrich; MULLER, Sibylle; KUBAS, Holger; MEYER, Udo; HECHENBERGER, Mirko; KAUSS, Valerjans; ZEMRIBO, Ronalds; WO2012/52451; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6443-85-2 ,Some common heterocyclic compound, 6443-85-2, molecular formula is C7H6N2, 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.

A mixture of 2-(pyridin-3-yl)acetonitrile (1 g, 8.47 mmol, 1.00 equiv), Raney nickel (1 g, 17.24 mmol, 1.00 equiv) and ammonium hydroxide (3 mL) in methanol (15 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight. The catalyst was removed by filtration through a pad of Celite and washed with several portions of methanol. The filtrate and washings were combined and concentrated under vacuum to give 940 mg (45%) of 2-(pyridin-3-yl)ethanamine as a yellow oil. LC-MS: (ES, m/z): 164 [M+CH3CN+H]+, 123 [M+H]+, 106.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6443-85-2, 2-(Pyridin-3-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Board of Trustees of the Leland Stanford Junior University; Auckland UniServices Limited; Ruga Corporation; Giaccia, Amato; Lai, Edwin; Razorenova, Olga; Chan, Denise; Hay, Michael Patrick; Bonnet, Muriel; Sun, Connie; Tabibiazar, Ray; Yuen, Po-wai; US2015/329503; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 156072-86-5, 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. 156072-86-5, name is 5-Bromo-3-methylpicolinonitrile. A new synthetic method of this compound is introduced below.

Step B 5-bromo-3-methylpyridine-2-carboxylic acid To a solution of 5-bromo-3-methylpyridine-2-carbonitrile (3.9 g, 20 mmol) in ethanol (30 mL) was added 6.0 M sodium hydroxide in water (15 mL), and the reaction was stirred at 80 C. for 1.5 h. The reaction mixture was concentrated, diluted with water and partitioned in EtOAc. The aqueous phase was acidified to pH 2-3. The product then was extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered and concentrated to give 4.2 g (98% yield) of the desired product as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156072-86-5, 5-Bromo-3-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Huang, Taisheng; Feng, Hao; Kong, Lingquan; Wang, Anlai; Ye, Hai Fen; US2013/96144; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem