Pyridine-derivatives

Synthetic Route of 170886-13-2, 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. 170886-13-2, name is 2-(Trifluoromethyl)pyridin-4-ol. A new synthetic method of this compound is introduced below.

A mixture of 2-(trifluoromethyl)pyridin-4-ol (100 mg, 0.613 mmol) and Lawesson?s reagent (123.99 mg, 0.307 mmol) in toluene (10 mL) was refluxed for 2 hours. Excess solvent was evaporated under reduced pressure. The residue was purified by automate column chromatography to give the desired product (75 mg, 68% yield). LC-MS: m/z: 180 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,170886-13-2, 2-(Trifluoromethyl)pyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; HELMHOLTZ-ZENTRUM FUeR INFEKTIONSFORSCHUNG GMBH; AHMED, Ahmed S. A.; EMPTING, Martin; HAMED, Mostafa; HARTMANN, Rolf W.; HAUPENTHAL, Joerg; HASTERKAMP, Thomas; KAMAL, Ahmed A. M.; MAURER, Christine K.; ROeHRIG, Teresa; SCHUeTZ, Christian; YAHIAOUI, Samir; ZENDER, Michael; (128 pag.)WO2020/7938; (2020); 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. 127406-56-8, name is 4-Pyridin-2-yl-benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Pyridin-2-yl-benzaldehyde

To a solution of 3, 4, 5-piperidinetriol, 2- (hydroxymethyl)-, (2S, 3R, 4R, [5S)] [(50MG,] 0. [31MMOL)] in methanol [(2ML)] was added 4- (2-pyridyl) benzaldehyde (280mg, 1. [53MMOL).] The mixture was stirred for 5 min until fully dissolved. The pH was adjusted to 5 by addition [OF METHANOLIC HCI (1M),] then (polystyrylmethyl) trimethylammonium cyanoborohydride (180mg, 0. [78MMOL)] was added. The resultant mixture was stirred at room temperature for 48 [H.] The crude reaction mixture was purified using a plug of acidic Dowex 50X4-200 resin [(1.] [5G),] which had been pre-washed with 10% aqueous hydrochloric acid, followed by water then methanol. The resin was eluted with methanol [(25ML)] to remove all non-basic side products. The desired compound was then eluted using a solution of 2: 2: 1 [METHANOL/WATER/AMMONIUM] hydroxide [(50ML).] The solution was concentrated to a small volume [(~LML)] and freeze dried. The resulting residue was crystallised from [METHANOL/ETHYL] acetate to give the title product (80mg, [78%).’H] NMR (d4-methanol) 8 2.63 [(1H,] dd, [J =] 9.6, 12. [2 HZ),] 2.73 [(1H,] dd, J = 5.1, 12. [2 HZ),] 3.11 [(1H,] m), 3.40 [(1H,] t, J [= 9.] 0 Hz), 3.53 [(1H,] m), 3.78 [(1H,] dd, J = 5.3, 9.0 Hz), 3.88-4. 03 (4H, m), 7.35 [(1H,] m), 7.50 [(2H,] d, J [= 8.] 3 Hz), 7.82-7. 90 (4H, m), 8.59 [(1H,] d, J = 4.9 Hz). MS [M/Z] 331.3 (M+H) +.

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, 127406-56-8, 4-Pyridin-2-yl-benzaldehyde.

Reference:
Patent; OXFORD GLYCOSCIENCES (UK) LTD; WO2004/7453; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 80194-68-9 ,Some common heterocyclic compound, 80194-68-9, molecular formula is C7H3ClF3NO2, 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.

The third step: 0.24g2-(4-(methylthio)phenoxy)acetyl hydrazine and0.25g3-Chloro-5-trifluoromethylpicolinic acid added to the tube with a thermowellIn a 50 mL three-necked flask, 4 mL of POCl3 was added, the stirrer was turned on, and the mixture was heated and stirred, followed by heating to 100 C. The progress of the reaction was followed by TCL, and when it was detected that the starting point of the reaction system disappeared, the reaction was stopped.Post-treatment: The reaction solution was slowly introduced into a 250 mL beaker containing ice cubes, and the pH was adjusted to 9-10 with Na2CO3. A large amount of yellow solid was produced at the bottom of the beaker, suction filtered, washed with water several times to neutral, and dried. After separation and purification by column chromatography (P: E = 3:1), the title compound was obtained.

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. 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guizhou University; Wu Jian; Xu Fangzhou; Wang Yanyan; Luo Dexia; Xue Wei; (37 pag.)CN108218848; (2018); A;,
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. 3222-48-8, name is 5-Cyano-2-picoline. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6N2

To a solution of 6-methylpyridine-3-carbonitrile (10.5 g, 25.7 mmol) in MeOH (80 mL) and NHs/MeOH (20 mL, 7 M) was added Raney-Ni (2.0 g) under N2 atmosphere. The suspension was degassed in vacuo and refilled with H2. The mixture was stirred for 12 hrs at 40 C under H2 (50 psi) atmosphere. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give (6-methyl-3-pyridyl)methylamine (9.5 g, compound 34b) as a light oil. 1H NMR (400 MHz, DMSO- d6) delta ppm: 8.36 (s, 1H), 7.62 (d, 7 = 8.0 Hz, 1H), 7.18 (d, / = 8.0 Hz, 1H), 3.69 (s, 2H), 2.42 (s, 3H). MS obsd. (ESI+) [(M+H)+]: 123.

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, 3222-48-8, 5-Cyano-2-picoline.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; LIANG, Chungen; MIAO, Kun; WANG, Jianping; YUN, Hongying; ZHENG, Xiufang; (230 pag.)WO2016/180695; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 71701-92-3, 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine, 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, 71701-92-3, blongs to pyridine-derivatives compound. Safety of 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine

A mixture of 3-bromo-2-chloro-5-(trifluoromethyl)pyridine (260 mg), trimethylsilyl acetylene (98.2 mg), tetrakis-triphenylphosphine palladium (0) (23.1 mg), copper iodide (3.8 mg), triethylamine (4 ml) and benzene (1 ml) was heated to 60 C. After the reaction mixture was stirred all night and all day, it was kept standing to cool to room temperature, and the, the solvent was distilled off in vacuo. To the residue was added ethyl acetate, and the organic layer was separated. The organic layer was washed with a saturated saline, and dried with anhydrous sodium sulfate. Then, the organic layer was filtrated and concentrated, and the residue was purified by the silica gel column chromatography affording the compound 2 (226 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71701-92-3, its application will become more common.

Reference:
Patent; Mitsubishi Tanage Pharma Corporation; US2012/258951; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52378-64-0, 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. 52378-64-0, name is (3-Bromopyridin-2-yl)methanol. A new synthetic method of this compound is introduced below.

Intermediate 6 3-Bromo-2-(5-chloro-2-iodo-phenoxymethyl)-pyridine Alternate Alkylation Method:(3-Bromo-pyridin-2-yl)-methanol (7.39 g, 39.30 mmoles), and triethylamine (7.15 mL, 51.3 mmoles) are combined in tetrahydrofuran (70 mL) under nitrogen. The solution is chilled to 0.6 C. with an ice bath. Methanesulfonyl chloride (3.35 mL, 43.28 mmol) is added dropwise over 20 min, controlling the exotherm such that the internal temperature does not exceed 5 C. Following the addition, the reaction is stirred over an ice bath. After 20 min HPLC analysis shows that the (3-Bromo-pyridin-2-yl)-methanol is fully consumed. Triethylamine hydrochloride is filtered using a fitted glass funnel, washing with cold THF (50 mL). The THF filtrate containing the mesylate is placed under nitrogen and chilled in an ice bath. 2-Iodo-5-chlorophenol (10.00 g, 39.30 mmoles) is added, followed by addition of sodium t-butoxide (4.10 g, 41.38 mmol) in two equal portions with a mild exotherm of about 5 C. for each addition. The ice bath is removed and the reaction allowed to stir overnight. The reaction is quenched with water (50 mL) and the lower aqueous layer allowed to slowly separate. The organic portion is washed with brine (25 mL), and then the brine and aqueous portions back-extracted with THF (10 mL). The organic portions are combined and dried over sodium sulfate, filtered, and concentrated to afford a rusty orange solid. The solid is dissolved in dichloromethane (25 mL) and chromatographed on an AnaLogix Inc., Intelliflash 180 automated chromatography instrument, version 1.8.0. using a gradient of 10-20% ethyl acetate/hexanes over 35 min to afford 11.0 g (65%) of the product as a yellow solid. 1H NMR (DMSO) delta 5.31 (2H, s), 6.85 (1H, dd), 7.25 (1H, m), 7.39 (1H, dd), 7.77 (1H, d), 8.17 (1H, d), 8.59 (1H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52378-64-0, (3-Bromopyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; US2010/69425; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1001756-21-3, 4-Amino-6-chloronicotinaldehyde, 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, Recommanded Product: 4-Amino-6-chloronicotinaldehyde, blongs to pyridine-derivatives compound. Recommanded Product: 4-Amino-6-chloronicotinaldehyde

To a solution of 4-amino-6-chloro-pyridine-3-carbaldehyde (1.6 g, 10.2 mmol) (from Example 24 supra) in DMSO (10 mL) at room temperature, was added dimethyl malonate (6.4 g, 48.4 mmol) and DL-proline (1.5 g, 13 mmol) successively. The reaction mixture was stirred at room temperature for 16 hours and then at 65 C. for 2 hours. The mixture was poured into water (80 mL), and extracted with dichloromethane (4*100 mL). The organic phase was washed with water (3.*100 mL), brine (50 mL) and dried to give a crude product. It was purified by chromatography (silica gel, 200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (3:2, v/v)) to give 7-chloro-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carboxylic acid methyl ester. (Yield 2.0 g, 82.3%). 1H NMR (300 MHz, DMSO): delta 12.41 (s, 1H), 8.86 (s, 1H), 8.64 (s, 1H), 7.22 (s, 1H), 3.83 (s, 3H). LC-MS: [M+H]+ 239.0.

The synthetic route of 1001756-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (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. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H2Br2N2O2

5-Bromo-2-(3-methoxyphenyl)-3-nitropyridine A stirred mixture of 2,5-dibromo-3-nitropyridine (0.2621 g, 0.930 mmol), 3-methoxyphenylboronic acid (0.155 g, 1.02 mmol), tetrakis(triphenylphosphine)-palladium (0.076 g, 0.065 mmol), and 2.0M sodium carbonate (2.4 mL, 4.80 mmol) in toluene (3.0 mL) and ethanol (1.0 mL) was heated to 70 C. After 2.5 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic extraction was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on silica gel (0-20% EtOAc in hexanes) to afford a yellow solid as 5-bromo-2-(3-methoxyphenyl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) delta ppm 8.91 (1H, d, J=2.2 Hz), 8.27 (1H, d, J=2.2 Hz), 7.42 (1H, m), 7.14 (3H, m), 3.86 (3H, s).

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, 15862-37-0, 2,5-Dibromo-3-nitropyridine.

Reference:
Patent; AMGEN INC.; US2010/331293; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 881-86-7, 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.881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate, molecular formula is C9H9NO4, molecular weight is 195.17, as common compound, the synthetic route is as follows.

To a solution of dimethyl pyridine-2,5-dicarboxylate 21-a (13.0 g, 66.6 mmol) in a mixture of THF (110 mL) and ethanol (110 mL) was added calcium chloride (29.6 g, 266 mmol). After stirring at room temperature for 30 minutes, the reaction was cooled to 0C, and sodium borohydride (3.78 g, 100 mmol) was added portion wise. After the addition was completed the reaction was stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride and dichloromethane were added, the organic layer was separated, and the aqueous phase was extracted twice with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide Intermediate 21-b as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 881-86-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2015/77866; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5349-17-7, 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.5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.9446, as common compound, the synthetic route is as follows.

To a solution of 2-Bromo-l-(4-pyridinyl)-l-ethanone hydrobromide (4.0 g, 14.4 mmol) in anhydrous ethanol (80 ml) is added NaBH4 (2.0 g, 52.8 mmol). The reaction mixture is stirred at RT for 2 h. The mixture is filtered and l-(2-Phenylethyl)piperazine (4.9 ml, 26.0 mmol) is added to the filtrate. The solution is heated to reflux and refiuxed for 5 h. Excessive ethanol is removed by distillation. The resulting pale yellow solid is dissolved in chloroform (80 ml), the insoluble parts are filtered off and the filtrate is concentrated by distillation under reduced pressure. The product is purified by chromatography on silica (MeOH/EtOAc, 5:1) to give a pale yellow solid; yield: 32 % ; chemical formula: Ci9H2SN3O; molecular weight: 311,42.1H NMR (300 MHz, CDCl3) delta 2.83 – 2.84 (m, 14H), 4.73 (dd, IH, J= 10.5 Hz, J = 3.8 Hz),7.20 – 7.30 (m, 5H), 7.31 (dd, 2H, J = 4.7 Hz, J = 1.5 Hz), 8.57 (dd, 2H, J = 4.4 Hz, J = 1.5Hz);FT-IR (KBr) 3420, 1639, 1458, 1409, 1128, 854, 696, 622 cm”1;EI MS mZz SlO [M-H+];HR MS m/z calcd for C19H24N3O [M-H+] C9H24N3O 310.191938, found 310.192050.

Statistics shows that 5349-17-7 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2007/73935; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem