Tag: M.W:100-200

Reference of 6313-54-8, 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. 6313-54-8, name is 2-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, 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.

Step 1 Preparation of Methyl-2-chloroisonicotinate To a solution of thionyl chloride (13.85 mL, 190.38 mmol) in toluene (50 mL) was added 2-chloropyridine-4-carboxylic acid (15 g, 95 mmol). The solution was heated to reflux for 3 hours. The resulting brown color solution was cooled to room temperature, and methanol (11.56 mL, 285.6 mmol) was added slowly dropwise. The mixture was brought to reflux for 15 minutes and became clear. The solution was then cooled to room temperature and poured into water (150 mL), basified with 50 percent sodium hydroxide and extracted with ethyl acetate (2*200 ml). The organic layer was separated and washed with brine, dried with magnesium sulfate, filtered and concentrated to yield the titled compound (11.93 g, 73percent) as a brown color solid. This was used in the next step without further purification.

According to the analysis of related databases, 6313-54-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia Corporation; US6509361; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63071-03-4, 2-Methoxy-6-methylpyridine, 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, HPLC of Formula: C7H9NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9NO

Example given for n = 7: An oven dried round bottom flask, equipped with magnetic stir bar was sealed under argon. To the flask, THF (10 mL) and n-BuLi (2.4 M in hexanes, 2.0 mL, 4.8 mmol) were added and cooled to 0 oC. To this flask, 2-methoxy-6-methylpyridine (0.50 mL, 4.1 mmol) was added drop wise via syringe, which resulted in a yellow color that intensified to brown over a few min. After 10 min, 1,6-dibromohexane (2.0 mL, 13 mmol) was added in one portion and the color rapidly dissipated. After an additional 2 h, the reaction was quenched upon addition of water. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. Final purification by column chromatography (0% -15% ethyl acetate in hexanes) afforded the desired compound (397 mg, 34%) along with the dimer 1,8-bis(6-methoxypyridin-2-yl)octane (180 mg, 27%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63071-03-4, 2-Methoxy-6-methylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Topczewski, Joseph J.; Lodge, Alexander M.; Yasapala, Sumana N.; Payne, Maurice K.; Keshavarzi, Pedrom M.; Quinn, Daniel M.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 21; (2013); p. 5786 – 5789;,
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. 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, molecular formula is C10H16N4, 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. Application In Synthesis of 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

A solution of 5-(4-methylpiperazin-1-yl)pyridin-2-amine (172 mg, 0.90 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (200 mg, 0.90 mmol) cesium carbonate (1.02 g, 3.13 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethlxanthene (77.7 mg, 0.13 mmol) in dioxane (10 ml) was flushed with argon before tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) was added and the resulting solution was heated at 90 C. for 18 h. The mixture was cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the aqueous layer was extracted with dichloromethane (2*25 mL). The organic layers were combined, dried over magnesium sulfate. The resulting mixture was filtered and concentrated in vacuo. The residue was triturated with methanol and dichloromethane and filtered, washed with ether and dried to give 6-chloro-4-[5-(4-methyl-piperazin-1-yl)-pyridin-2-ylamino]-2-methyl-2H-pyridazin-3-one (223 mg, 74%) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 571189-49-6.

Reference:
Patent; Berthel, Steven Joseph; Billedeau, Roland Joseph; Brotherton-Pleiss, Christine E.; Firooznia, Fariborz; Gabriel, Stephen Deems; Han, Xiaochun; Hilgenkamp, Ramona; Jaime-Figueroa, Saul; Kocer, Buelent; Lopez-Tapia, Francisco Javier; Lou, Yan; Orzechowski, Lucja; Owens, Timothy D.; Tan, Jenny; Wovkulich, Peter Michael; US2012/40949; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74784-70-6, 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 74784-70-6 as follows.

To a de-gassed mixture of 3- [3- (trifluoromethyl) pyridin-2-yl] pyrido [2,3-b] pyrazin-8- amine (72 mg, 0.25 MMOL), cesium carbonate (162 mg, 0.5 mmol), 2-amino-trifluoromethyl pyridine (45 mg, 0.25 mmol) in dioxane (5 mL) under nitrogen, add PD2DBA3 (11 mg) and xantphos (7 MG). Stir the mixture AT 100C for 3 hours, cool, add water (10 mL) and extract with EtOAc. Dry over NA2SO4, concentrate under vacuum. Purify by chromatography eluting with DICHLOROMETHANE/METHANOL/AMMONIUM hydroxide mixture to give the title compound. MS 437 (M + 1).’H NMR 6 (CDCI3) 9.42 (1H, s), 9.28 (1H, s), 9.11 (1H, d), 8.95 (1H, d), 8. 90 (IH, d), 8.72 (1H, s), 8.25 (1H, d), 7.89 (1H, d), 7.61 (1H, dd), 7.13 (1H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74784-70-6, its application will become more common.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/7652; (2005); 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. 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%.

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, 1480-87-1, 2-Fluoro-3-nitropyridine.

Reference:
Patent; Sichuan University; Yang Shengyong; Li Linli; (36 pag.)CN109180702; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
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. 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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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