Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 72990-37-5, 3-Chloroisonicotinaldehyde, 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 3-Chloroisonicotinaldehyde, blongs to pyridine-derivatives compound. Safety of 3-Chloroisonicotinaldehyde

Magnesium (86.5 mg, 3.60 mmol) was stirred vigorously under nitrogen for 30 min. THF (2 mL) and dibromoethane (2 drops) were added and the reaction mixture was warmed to 50 C. A solution of 4-bromotetrahydropyran (495 mg, 3.00 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 2 h. A solution of 3-chloro-4-pyridaldehyde (170 mg, 1.20 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 6 h, stirred at room temperature overnight and heated at reflux for 8 h. The reaction mixture was cooled to 0 C and quenched with sat aq NH4C1 (10 mL). The reaction mixture was diluted with EtOAc (40 mL) and the aqueous fraction was extracted with EtOAc (3 x 40 mL). The combined organic fractions were washed with sat aq Na2C03 (20 mL), dried (MgS04) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the crude title compound as a pale yellow gum (69.0 mg, 25%). LCMS (ES+): 228.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72990-37-5, 3-Chloroisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Proximagen Limited; EVANS, David; CARLEY, Allison; STEWART, Alison; HIGGINBOTTOM, Michael; SAVORY, Edward; SIMPSON, Iain; NILSSON, Marianne; HARALDSSON, Martin; NORDLING, Erik; KOOLMEISTER, Tobias; WO2011/113798; (2011); A2;,
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. 113293-71-3, name is (6-Aminopyridin-3-yl)methanol. A new synthetic method of this compound is introduced below., Quality Control of (6-Aminopyridin-3-yl)methanol

General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

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, 113293-71-3, (6-Aminopyridin-3-yl)methanol.

Reference:
Article; Mohyeldin, Mohamed M.; Busnena, Belnaser A.; Akl, Mohamed R.; Dragoi, Ana Maria; Cardelli, James A.; El Sayed, Khalid A.; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 299 – 315;,
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. 178876-82-9, name is Methyl 6-amino-5-bromopicolinate. A new synthetic method of this compound is introduced below., name: Methyl 6-amino-5-bromopicolinate

A solution of ethyl 2-mercaptoacetate (1.473 mL) in DMF (48 mL) was ice-cooledand treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 h methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T.R. Kelly and F. Lang, J. Org. Chem. 61,1996, 4623-4633) was added and the mixture stirred for 16h at room temperature. Thesolution was diluted with EtOAc (1 L), washed with water (3 x 300 mL), dried and evaporated to aoout 10 ml_. The white solid was filtered off and washed with a little EtOActo give the ester (0.95g); LC/MS (APCI~) m/z223 ([M-H]-, 100%).

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, 178876-82-9, Methyl 6-amino-5-bromopicolinate.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/12396; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71255-09-9, Adding some certain compound to certain chemical reactions, such as: 71255-09-9, name is 2-Methoxynicotinaldehyde,molecular formula is C7H7NO2, 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 71255-09-9.

[0706] A mixture of trans-3-(4-amino-phenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1 eq.), 2-methoxy-3-formyl-pyridine (1.05 eq.), sodium triacetoxyborohydride (3.4 eq.) and acetic acid (3.4 eq) was stirred in anhydrous 1,2-dichloroethane for 16 hours. The reaction mixture was concentrated under reduced pressure, quenched with saturated solution of sodium bicarbonate in water and concentrated again. The residue was purified by preparative HPLC (Hypersil C18, 8 mum, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield the desired products. The following two compounds were prepared according to the procedure above: trans-3-(4-[(2-methoxy-3-pyridyl)methyl]aminophenyl)-1-[4-(4-methyl-piperazino)cyclohexyl]-1H-pyrazolo [3,4-d]pyrimidin-4-amine Diacetate [0707] 1H NMR (DMSO-d6, 400 MHz) delta 8.18 (s, 1H), 8.06 (dd, 1H), 7.61 (d, 1H), 7.35 (d, 2H), 6.95 (dd, 1H), 6.69 (d, 2H), 6.51 (t, 1H), 4.60 (m, 1H), 4.26 (d, 2H), 3.94 (s, 3H), 2.64 (s, 3H), 2.6-2.2 (br, 9H), 2.13 (s, 3H), 2.05 (m, 6H), 1.91 (s, 6H), 1.46 (m, 2H); [0708] RP-HPLC (Delta Pak C18, 5 mum, 300A, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 12.07 min. [0709] MS: MH+ 528.

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. 71255-09-9, 2-Methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hirst, Gavin C.; Rafferty, Paul; Ritter, Kurt; Calderwood, David; Wishart, Neil; Arnold, Lee D.; Friedman, Michael M.; US2004/6083; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 109-04-6 , The common heterocyclic compound, 109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, 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 n-BuLi (15.00 mmol) in diethyl ether (30.0 mL) at78 C was added dropwise to a solution of bromopyridine(15.00 mmol) in diethyl ether (25.0 mL). The resulting solutionwasstirred at 78 C for 2 h. And then, the solution of Bu3SnCl orMe3SnCl (15.00 mmol) in THF (10.0 mL) was added dropwise andstirred at 78 C for another 3 h. The resulting deep-red solutionwas warmed to room temperature over night and a heavy precipitateformed. Hydrolysis was achieved with a saturated aqueoussolution of NH4Cl. Subsequent treatments (Et2O extraction, dryingon anhydrous Na2SO4, concentration and flash chromatography)afforded pure product.

The synthetic route of 109-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1335210-23-5, 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. 1335210-23-5, name is 1-(2,2-Dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid, molecular formula is C13H17NO8, 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.

Compound 1 (20.0 g, 63.4 mmol) and dichloromethane (150 mL) were added to the reaction flask, and the mixture was dissolved by stirring at room temperature. The temperature was lowered to 15-20 C, N, N-carbonyldiimidazole (13.9 g, 85.7 mmol) was added, and the reaction was kept under nitrogen protection for 2 hours. Compound 2 (10.0 g, 69.9 mmol) was added dropwise, and the temperature was raised to room temperature and reacted for 2 hours. The reaction solution was washed with a 1N aqueous HCl solution (100 mL), a 5% aqueous sodium carbonate solution (130 mL), and a saturated saline solution (100 mL) in this order. The organic phase was concentrated to dryness, and the obtained oil was separated by column chromatography [mobile phase: n-hexane: ethyl acetate (2: 1)] to obtain a white solid powder product compound 3 (18.9 g, 68%)

According to the analysis of related databases, 1335210-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anhui Baker Bio-pharmaceutical Co., Ltd.; Wang Zhibang; Xu Jingkun; Tian Lei; Zhang Zuliang; Liao Jiehai; Zou Hui; Wang Yao; Liu Yang; (20 pag.)CN110655517; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2587-02-2, 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.2587-02-2, name is 2,6-Dichloropyridin-4-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.

Intermediate 35 : 4-Chloro-6-methoxy-pyridine-2-carboxylic acid 35.1 : 2-Chloro-6-methoxy-pyridin-4-ylamine To a solution of 1.84 g (44.0 mmol) sodium in 40 mL MeOH was added 6.72 g (40.0 mmol) 2,6- dichloro-pyridin-4-ylamine. The reaction mixture was stirred at 150 C for 30 min under microwave irradiation. The solvent was evaporated and ice water was added. The precipitate was filtered off, washed with water and dried. yield: 5.00 g (79 %); ESI-MS: m/z = 159 (M+H)+; Rt(HPLC): 0.41 min (method 5)

Statistics shows that 2587-02-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloropyridin-4-amine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; WO2013/87805; (2013); 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. 153034-94-7, name is 2-Fluoro-4-iodo-5-picoline, molecular formula is C6H5FIN, 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-Fluoro-4-iodo-5-picoline

Palladium acetate (0.04 mmol, 10 mg) was stirred with 1, 3-bis (diphenylphosphino) propane (18 mg, 0.04 mmol) in DMF (0.5 mL) for 10 minutes. A mixture of 2-fluoro-4-iodo-5-methyl pyridine (0.42 mmol, 100 mg), ethyl-1-piperidinecarboxylate (0.5 mmol, 0.08 mL) and cesium carbonate (275 mg, 2 equiv) in DMF (1.5 mL) was then added, stirred vigorously, and heated in the microwave to 160 C for 10 minutes. The resulting black mixture was poured onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes gradient) to afford 61 mg of the title compound as a yellow oil (54%). Rt = 6.70 minutes; MS FIA 267.1 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 153034-94-7.

Reference:
Patent; VERTEX PHARMACEUTICALS, INC.; WO2005/68468; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16133-25-8, Pyridine-3-sulfonyl chloride, 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, Formula: C5H4ClNO2S, blongs to pyridine-derivatives compound. Formula: C5H4ClNO2S

5- (2-fluorophenyl) pyrrole-3-carbaldehyde 10g, 4- dimethylaminopyridine 1.3g, triethylamine 7.5g and acetonitrile (40ml) added to the reaction flask, stirred at room temperature; pyridine-3-sulfonyl chloride 11.3g and acetonitrile (10ml), the reaction flask was added dropwise; the reaction was heated to 45 1.5 hours; cooled to 25 , was added water (30ml); the system with concentrated hydrochloric acid adjusted to ph 4-5, stirred for half an hour at 25 deg.] C; was cooled to 0-5 deg.] C stirred for 1 hour; the filter cake with acetonitrile: water (1: 2) 30ml rinsed again with water (20ml) was rinsed 2 times, 50 deg.] C and dried in vacuo to give 5- (2-fluorophenyl yl) -1- (pyridin-3-sulfonyl) pyrrole-3-carbaldehyde 15g;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16133-25-8, Pyridine-3-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang Sincerity Pharmaceutical Co., Ltd.; Mao Liping; (9 pag.)CN104860926; (2017); B;,
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. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

i-PrMgCl (0.32 mL, 0.64 mmol) was added to 3-iodo-lH- pyrazolo[3,4-b]pyridine (3.1 mL, 0.61 mmol) in THF (3 mL) at O0C. After 10 minutes, another portion of i-PrMgCl (0.32 mL, 0.64 mmol) was added. After 10 minutes, neat cyclopropanecarbaldehyde (0.074 mL, 0.98 mmol) was added dropwise and stirred at O0C for 1 hour. The mixture was diluted with EtOAc (5 mL) and aqueous ammonium chloride, and extracted with EtOAc (2 X 5 mL). The resulting residue was purified via flash chromatography eluting with EtOAc to afford cyclopropyl(l H-pyrazolo [3, 4-b]pyridin-3- yl)methanol (0.052 g, 0.28 mmol, 44.9% yield).

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

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