Category: pyridine-derivatives

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. 1480-87-1, name is 2-Fluoro-3-nitropyridine. A new synthetic method of this compound is introduced below., name: 2-Fluoro-3-nitropyridine

1.5 g of 2-fluoro-3-nitropyridine,1.5 g of tert-butyl trans-(4-aminocyclohexyl)carbamate was dissolved in acetonitrile.4 mL of triethylamine was added and reacted at 85 C for 12 hours.The reaction solution was cooled to room temperature and concentrated under reduced pressure.Adding an aqueous solution of citric acid, heating and stirring at 30 C, and vacuum filtration.The filter cake was washed with a small amount of diethyl ether to give an orange solid, which was intermediate XI.The yield was 65%.

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Reference:
Patent; Sichuan University; Yang Shengyong; Li Linli; (36 pag.)CN109180702; (2019); A;,
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Synthetic Route of 7340-22-9, Adding some certain compound to certain chemical reactions, such as: 7340-22-9, name is 3-(2-pyridyl)acrylicacid,molecular formula is C8H7NO2, 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 7340-22-9.

General procedure: Add the acid (III) to the dried 10 mL round bottom flask and add the solvent to dichloromethane.Stirring was started, then 1.1 eq of oxalyl chloride was added to 0.1 eq of N,N-dimethylformamide, and the reaction was treated after 2 h.Concentration in vacuo gave the compound acid chloride (IV). Compound 2 was dissolved in DCM and 1.5 eq of triethylamine (TEA) was added.After stirring for 1-2 min, add 1.2 eq of acid chloride and stir at room temperature for 1 h.The reaction was completely detected by TLC, quenched with distilled water and extracted three times with DCM.The organic phase was combined, dried over anhydrous Na2SO4, filtered, and then evaporated.(Petroleum ether / ethyl acetate) gave the title compound 37-42 (white amorphous solid).

According to the analysis of related databases, 7340-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nankai University; Chinese Academy Of Medical Sciences Xueyebing Hospital (Xueyexue Institute); Tianjin Shang De Yaoyuan Technology Co., Ltd.; Zhang Quan; Chen Yue; Gao Yingdai; Ding Yahui; Li Ye; Lian Lihui; Ge Weizhi; (22 pag.)CN109206389; (2019); A;,
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Application of 62150-45-2, 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 62150-45-2, name is 4-Bromopyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

e) C- (4-Bromopyridin-2-vl) methylamine; A solution of 18.70 g 4-bromopyridine-2-carbonitrile [62150-45-2] in 200 mi of tetrahydrofuran is admixed under argon dropwise with 500 ml of 1 M borane-tetrahydrofuran complex solution. The reaction solution is subsequently left to stand at room temperature for 16 hours. The reaction solution is cooled to 0C, admixed dropwise with 500 ml of 2M HCI and heated to reflux for 30 minutes. The reaction solution is cooled to room temperature, basified with 2M NaOH, saturated with sodium chloride and extracted with tetrahydrofuran (3 x 300 ml). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (Si02 60F).

According to the analysis of related databases, 62150-45-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90305; (2005); A1;,
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Pyridine | C5H5N – PubChem

Electric Literature of 1111637-68-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1111637-68-3 as follows.

To a solution of 5-bromo-3-fluoro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 4.65mmol) in 1,4-dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.77 g, 6.98 mmol), potassium acetate (1.37 g, 13.95 mmol) and l, l’-bis(diphenylphosphino)ferrocene-palladium(n)dichloride (340 mg, 0.46mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 2 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether ) affording 3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (240 mg, 20%): NMR (400 MHz, Chloroform-d) delta 11.44 (m, 1H), 8.73 (d, 7= 1.6 Hz, 1H), 8.46 (d, 7= 1.2 Hz, 1H), 7.10 (m, 1H), 1.39 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-68-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 677728-92-6, 2-Fluoropyridine-5-carbaldehyde, 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, 677728-92-6, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Fluoropyridine-5-carbaldehyde

EXAMPLE 234. 5-(l,3-DIOXOLAN-2-YL)-2-FLUORO-3-(4,4,5,5-TETRAMETHYL-l,3,2- DIOXABOROLAN-2-YL)PYRIDINESTEP 1: 5-(l,3-DIOXOLAN-2-YL)-2-FLUOROPYRIDINE[00611 ] 6-Fluoronicotinaldehyde (21.96 g, 176 mmol) was suspended in toluene (340 mL) and ethylene glycol (10.4 mL, 186 mmol) and p-toluenesulfonic acid (Acros, 15% in acetic acid, 1.10 mL) were added. The flask was fitted with a Dean-Stark head and a reflux condenser, and placed in a preheated oil bath (120 0C) and the reaction was stirred. After 45 minutes, the reaction was cooled to room temperature. The reaction was diluted with saturated sodium bicarbonate (50 mL), water (150 mL) and EtOAc (150 mL). The layers were separated and the aqueous phase was extracted with EtOAc. The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (600 mL fritted filter with about 3 inches of silica gel; DCM to 100: 1 to 50: 1 DCM / MeOH to 40: 1 DCM / MeOH) to give 19.055 g of 5-(l,3-dioxolan-2-yl)-2-fluoropyridine. m/z (ESI, +ve ion) 170 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; AMGEN INC.; ANDREWS, Kristin; BO, Yunxin, Y.; BOOKER, Shon; CEE, Victor, J.; D’ANGELO, Noel; HERBERICH, Bradley, J.; HONG, Fang-Tsao; JACKSON, Claire, L., M.; LANMAN, Brian, A.; LIAO, Hongyu; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; PETTUS, Liping, H.; REED, Anthony, B.; SMITH, Adrian, L.; TADESSE, Seifu; TAMAYO, Nuria, A.; WU, Bin; WURZ, Ryan; YANG, Kevin; WO2010/126895; (2010); A1;,
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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. 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. A new synthetic method of this compound is introduced below., Computed Properties of C8H7N3

solid I (2.61 g, 18.0 mmol) was added to a solution of KOH in H2O (50%, 10 ml). 2-Chloromethyl ethyl ether (1.46 g, 15.4 mmol) was added dropwise and the reaction mixture was refluxed for 3.5 h. Water (10 ml) was added to the reaction mixture and the organic phase was separated. The aqueous layer was further extracted several times with DCM and the combined organic layer was washed with water and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (DCM:MeOH = 9:1). L2 was obtained as a slightly yellow liquid. Yield: 34%. 1H NMR (200.13 MHz, DMSO-d6): delta = 8.58 (ddd, 1 H, 6-pyH), 8.09 (ddd, 1 H, 3-pyH), 7.87 (ddd, 1 H, 4-pyH), 7.32 (d, 1 H, 5-imH), 7.34 (ddd, 1 H, 5-pyH), 7.03 (d, 1 H, 4-imH), 4.75 (t, 2 H, NCH2CH2OCH3), 3.65 (t, 2 H, NCH2CH2OCH3), 3.19 (s,3 H, CH3) ppm. 13C NMR (50.33 MHz, DMSO-d6): delta = 151.0 (2-pyC), 149.3 (6-pyC), 143.9 (2-imC), 137.8 (4-pyC), 128.5 (4-imC),125.5 (5-imC), 123.3 (5-pyC), 122.9 (3-pyC), 72.1 (NCH2CH2OCH3),58.6 (CH3), 47.6 (NCH2CH2OCH3) ppm (Fig. S35, Supporting information). IR (diamond, ATR): ~v = 2892, 1588 (s), 1566, 1486 (s),1459 (vs), 1407, 1298, 1277, 1211, 1117 (vs), 1038, 1012, 992, 969, 917, 833, 791 (vs), 743 (vs), 708 (vs), 667, 624, 404 cm-1 (Fig. S22, Supporting information). APCI-MS (MeOH) m/z (rel. abundance,fragment) = 204.1132 (100%, [HL2]+) (Fig. S8, Supporting information). Elemental analysis (%)Anal. Calc. for C11H13N3O(203.24 g mol1): C, 65.01; H, 6.45; N, 20.67. Found: C, 64.69; H,6.46; N, 20.79%. UV-Vis (MeCN): lambdamax(epsilon) = 294 (15,850), 266(12,180) nm (M-1 cm-1) (Fig. S37, Supporting 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, 18653-75-3, 2-(1H-Imidazol-2-yl)pyridine.

Reference:
Article; Huxel, Timo; Skaisgirski, Michael; Klingele, Julia; Polyhedron; vol. 93; (2015); p. 28 – 36;,
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Synthetic Route of 55304-75-1, Adding some certain compound to certain chemical reactions, such as: 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine,molecular formula is C6H2Cl2F3N, 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 55304-75-1.

Nine separate sealed tubes, each containing a mixture of 2,6-dichloro-3-(trifluoromethyl)pyridine (10.0g, 46.3 mmol) and ammonium hydroxide (91 g, 100 mL, 2600 mmol) were stirred at 100 C. for 12 h. After cooling to rt, the contents of all of the sealed tubes were combined and the solvents were concentrated in vacuo. Purification of the (FCC, SiO2; 5-20% EtOAc/petroleum ether) afforded the title compound as a colorless oil (57 g, 66%), which solidified upon standing. MS (ESI): mass calcd. for C6H4ClF3N2, 196.0; m/z found, 196.8 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.69 (d, J=8.0 Hz, 1H), 6.42 (d, J=8.4 Hz, 1H), 5.01 (br s, 2H).

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. 55304-75-1, 2,6-Dichloro-3-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Gyuris, Mario; Laforteza, Brian Ngo; Lebold, Terry Patrick; Meyer, Stephen Todd; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; Wade, Warren Stanfield; Gerencser, Janos; (87 pag.)US2018/111933; (2018); A1;,
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Synthetic Route of 6635-90-1, 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. 6635-90-1, name is 2-Methoxy-4-methyl-5-nitropyridine, molecular formula is C7H8N2O3, 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.

b 5-Amino-2-methoxy-4-methylpyridine A mixture of stannous chloride dihydrate (41 g) and concentrated hydrochloric acid (40 ml) was added slowly to a solution of 2-methoxy-4-methyl-5-nitropyridine (5.1 g) in acetic acid (40 ml), maintaining the temperature below 35 C. The resulting mixture was stirred at room temperature for 2 hours, and then allowed to stand overnight in the refrigerator. The solid was collected and both solid and supernatant were separately basified with a 20% sodium hydroxide solution. The product was extracted with chloroform, combined, dried (anhydrous magnesium sulfate) and concentrated to give 3.9 g of the title compound as a solid, suitable for use in the next reaction.

According to the analysis of related databases, 6635-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US5366972; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10128-91-3, Adding some certain compound to certain chemical reactions, such as: 10128-91-3, name is Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate,molecular formula is C7H7NO3, 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 10128-91-3.

Methyl 2-hydroxynicotinate (500 mg, 3.27 mmol) and N-bromosuccinimide (756 mg, 4.25 mmol) were dissolved in dichloromethane and the mixture was stirred at 50 C for 48 hours. The mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was filtered with a small amount of dichloromethane to obtain the title compound (0.3 g, yield: 40%, yellow solid). *H NMR (500MHz, DMSO-d6) d 8.07 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 5.0 Hz, 1H), 3.75 (s, 3H)

According to the analysis of related databases, 10128-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WELLMARKER BIO CO., LTD.; LEE, Hyunho; PARK, Chun-Ho; HUR, Sun Chul; MOON, Jai-Hee; SHIN, Jae-Sik; HONG, Seung-Woo; PARK, Yoon-Sun; KIM, Joseph; LEE, Sohee; KIM, Hyojin; PARK, Hyebin; (83 pag.)WO2019/182274; (2019); A1;,
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Reference of 878207-92-2, 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.878207-92-2, name is Methyl 6-chloro-3-methylpicolinate, molecular formula is C8H8ClNO2, molecular weight is 185.61, as common compound, the synthetic route is as follows.

To a stirred solution of methyl 6-chloro-3-methylpicolinate (1.0 g, 5.4 mmol) in 1,4-Dioxane (20 mL) were added, 2-(3-((4-Methoxybenzyl)oxy)-5-(trifluoromethyl)phenyl)-4,4,5,5-tetra methyl- 1, 3, 2-dioxaborolane (3.5 g, 8.6 mmol), Na2C03 (1.7 g, 16.2 mmol) in H20 (2 mL) and the mixture was degassed for 10 mins. To this, PdCl2(dppf) (0.16 g, 0.22 mmol) was added and the reaction mixture was heated to 100 C overnight. After completion (TLC), it was diluted with Ethyl acetate (50 mL) and filtered through a pad of celite. The filtrate was collected, concentrated and purified by flash chromatography using Ethyl acetate: Hexanes to afford the titled compound (1.2 g, 51%) as white solid.

The chemical industry reduces the impact on the environment during synthesis 878207-92-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LUPIN LIMITED; MADAN, Sachin; TALE, Prashant, Vitthalrao; ZADE, Seema, Prabhakar; PATIL, Amolsing, Dattu; KULKARNI, Sanjeev, Anant; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2015/162538; (2015); A1;,
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Pyridine | C5H5N – PubChem