Day: May 13, 2021

Adding a certain compound to certain chemical reactions, such as: 89937-77-9, Methyl 1,2-dihydro-2-oxopyridine-4-carboxylate, 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, 89937-77-9, blongs to pyridine-derivatives compound. Recommanded Product: 89937-77-9

LiH (78 mg) was suspended in DMF (5 ml), and a suspension of methyl-2-oxo-1,2-dihydropyridine-4-carboxylate (500 mg) in DMF (5 ml) was added dropwise thereto at room temperature. The suspension was stirred as it was, and a solution of 1-indo-2-methylpropane (506 mul) in DMF (5 ml) was added dropwise thereto over 10 min, followed by stirring at 50C for 15 hours. To the reaction solution was added 1M HCl at 0C, followed by extraction with EtOAc, and the organic layer was washed with saturated brine, dried over anhydrous MgSO4, and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:EtOAc=90:10 to 50:50) to obtain methyl-1-isobutyl-2-oxo-1,2-dihydropyridine-4-carboxylate (440 mg) as white powders.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89937-77-9, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; EP2003132; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 849020-87-7, 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.849020-87-7, name is 6-Hydroxy-4-(trifluoromethyl)nicotinic acid, molecular formula is C7H4F3NO3, molecular weight is 207.1068, as common compound, the synthetic route is as follows.

Diethyl chlorophosphate (0.045 ml, 0.312 mmol) was added to a solution of 6-hydroxy-4-(trifluoromethyl)nicotinic acid (0.065 g, 0.312 mmol) in pyridine, anhydrous (0.945 ml, 11.70 mmol) at room temperature under nitrogen. After stirring for lh, this solution was added to a vial containing 6-fluoro-4-(4- methylpiperazin-1-yl)-3′-(mo holinomethyl)-[l, -biphenyl]-3-amine (step 3 from (a): 0.030 g, 0.078 mmol) under nitrogen and the reaction was heated to 70C for 3 hours. The pyridine was removed under reduced pressure and LCMS of the residue (dissolved in DCM, MeCN and MeOH) indicated complete conversion to the desired product. The mixture was loaded onto celite purified by flash chromatography [0.5-10% DCM/MeOH + 1% NH4OH] to methylpiperazin-1-yl)-3′-(mo holinomethyl)-[l,Gamma- biphenyl]-3-yl)-6-oxo-4-(trifluoromethyl)-l,6-dihydropyridine-3-carboxarnide (0.024 g, 0.042 mmol, 53.6% yield) as a clear film. NMR (500 MHz, DMSO-d6) delta = 9.53 (s, 1H), 7.94 (s, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.46 – 7.42 (m, 2H), 7.40 – 7.38 (m, 1H), 7.32 (d, J=7.3 Hz, 1H), 7.08 (d, J=12.5 Hz, 1H), 6.81 (s, 1H), 3.60 – 3.57 (m, 4H), 3.53 (s, 2H), 2.93 (br. s., 4H), 2.38 (br. s., 4H), 2.24 (s, 3H); LCMS [M+H]+ 574 g/mol.

The chemical industry reduces the impact on the environment during synthesis 849020-87-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-79-0, 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 69045-79-0, name is 2-Chloro-5-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (S)-1-(phenyl-3-boronic acid)-ethyl]-carbamic acid tert-butyl ester (1.29 g, 4.86 mmol) and 2-chloro-5-Iodo-pyridine (1.4 g, 11.4 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (4.75 g, 14.6 mmol) and water (5 mL). Argon was bubbled in to the above mixture for 10 min, and Pd(PPh3)4 (280 mg, 0.24 mmol) was added. The reaction mixture was stirred at 100 C. for 18 hand then cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2¡Á100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (785 mg, 69%) as yellow oil. [0147] 1H NMR (DMSO d6, 400 MHz): delta 1.28 (d, 3 H, J=6.8 Hz), 4.04 (q, 1 H, J=6.8 Hz), 7.4-7.45 (m, 2H), 7.5-7.55 (m, 1H), 7.61 (d, 1H J =7.8 Hz,), 7.72 (s, 1H), 8.15 (dd, 1H, J=8.3, 2.5 Hz,), 8.73 (d, 1H, J=3.3 Hz).

According to the analysis of related databases, 69045-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wu, Yong-Jin; Sun, Li-Qiang; L’Heureux, Alexandre; US2004/110754; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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