Tag: M.W:100-200

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. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below., Quality Control of 2-Nitropyridin-3-amine

To a stirred suspension of 2-nitro-pyridin-3-ylamine (25.0 g, 179.7 mmol) andsodium acetate (15.5 g, 188.7 mmol) in acetic acid (150 mL), a solution of bromine (13.8 mL, 269.6 mmol) in acetic acid (50 ml) was added dropwise and the reaction mixture was stirred overnight. The acetic acid was removed under reduced pressure. The residue wascooled to 0C, neutralized with saturated sodium bicarbonate solution to adjust the pH to-7, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Theresidue was triturated with ethyl acetate to afford compound (34.4 g, 88% yield) as a

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, 13269-19-7, 2-Nitropyridin-3-amine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; (90 pag.)WO2019/3143; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, 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, name: Imidazo[1,2-a]pyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. name: Imidazo[1,2-a]pyridine-2-carboxylic acid

Working Example 47 To a mixture of 3-methoxymethyl-1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (500 mg) obtained in Reference Example 14, imidazo[1,2-a]pyridine-2-carboxylic acid (211 mg), triethylamine (657 mg) and N,N-dimethylformamide (3 ml) is added dropwise under ice-cooling, while stirring, a solution of diethyl cyanophosphonate (277 mg) in N,N-dimethylformamide (1 ml), and the mixture is stirred for one hour. The reaction mixture is poured into ice-water and extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent: ethyl acetate), followed by recrystallization to give 2-[2-methoxymethyl-4-(3,4,5-trimethoxybenzyl)piperazin-1-ylcarbonyl]imidazo[1,2-a]-pyridine as colorless prisms (354 mg), m.p. 129-130C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP368670; (1990); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H3ClN2

(E)-N-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(3-hydroxyphenyl)-2-methylacrylamide (1.0 g, 2.81 mmol), 4-chloropicolinonitrile (428 mg, 3.09 mmol) and cesium carbonate (2.75 g, 8.43 mmol) were combined and stirred in DMF. The reaction mixture was heated at 100 C. overnight and then cooled to rt. The mixture was filtered to remove cesium carbonate, the collected precipitate was washed with EtOAc, and the combined filtrate was concentrated. Purification by column chromatography (SiO2, 0-80% EtOAc in hexanes) provided the title compound (883 mg). LCMS, FA: Rt=2.15 min, [MH+ 458.0].

With the rapid development of chemical substances, we look forward to future research findings about 19235-89-3.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2006/160803; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56946-65-7, Adding some certain compound to certain chemical reactions, such as: 56946-65-7, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine,molecular formula is C8H7Cl2N, 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 56946-65-7.

A 25-mL round bottom flask was charged with 2,4-dichloro-6,7-dihydro-5H- cyclopenta[Z?]pyridine (0.300 g, 1.59 mmol), 5-chloro3-pyridinyl boronic acid (0.301 g, 1.91 mmol), tetrakis(triphenylphosphine)palladium(0) (0.092 g, 0.08 mmol), and CS2CO3 (1.56 g, 4.78 mmol). Toluene (8 ml), EtOH (2 ml) and water (4 ml) were added. The resulting mixture was stirred under Ar at 90 C for 2.5 h. After this time, the mixture was cooled to rt, filtered through celite, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on silica using hexane/ethyl acetate (10:0 to 0: 10) as eluent to afford the title compound (0.127 g, 30%) as a white solid. MW = 265.14. ]H NMR (CDC13, 500 MHz) delta 8.99 (d, / = 2.0 Hz, 1H), 8.59 (d, / = 2.5 Hz, 1H), 8.30 (t, / = 2.5 Hz, 1H), 7.50 (s, 1H), 3.15 (t, / = 7.5 Hz, 2H), 3.05 (t, / = 7.5 Hz, 2H), 2.21 (quin, / = 7.5 Hz, 2H).

According to the analysis of related databases, 56946-65-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89466-17-1, 6-Bromo-5-methylpyridin-2-amine, 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 6-Bromo-5-methylpyridin-2-amine, blongs to pyridine-derivatives compound. Safety of 6-Bromo-5-methylpyridin-2-amine

To a solution of 1 -(2,2-difluoro-l,3-benzodioxol-5-yl)cyclopropanecarboxylic acid (5g) in toluene (5OmL) and dimethylformamide (1 .25mL) was slowly added thionyl chloride(3.63mL) and the reaction mixture was stirred for about 3h at about 80C. The reaction mixture was concentrated under reduced pressure at about 50C. To the obtained residue in dichloromethane (lOmL) were added 6-amino-2-bromo-3-methylpyridine (3.86g) in dichloromethane (SOmL) and pyridine (SmL) at about room temperature. The reaction mixture was maintained for about 3h at about room temperature and water was added toit. The two layers were separated and the organic layer was treated with 10% hydrochloric acid solution and then with sodium bicarbonate solution. The organic layer was washed with water and brine solution, treated with charcoal, filtered, concentrated under reduced pressure at about 50C and was co-distilled with hexane. Hexane was added to the obtained residue and the mixture was stirred for about 6h. The solid obtainedwas filtered and dried at about 60C for about 8h. Yield: 65.3g (76%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89466-17-1, 6-Bromo-5-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; BHIRUD, Shekhar Bhaskar; KADAM, Suresh Mahadev; KANSAGRA, Bipin Parsottam; BHADANE, Shailendra Nilkanth; KALE, Shrikrishna Kantilal; PATIL, Ulhas Digambar; (57 pag.)WO2017/56031; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10128-72-0, 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 10128-72-0 as follows.

[0163] To a DMF (15 mL) solution of the chloride (300 mg, 1.5 mmol, 1.0 eq) and phenol (230 mg, 1.5 mmol, 1.0 eq) was added K2C03 (621 mg, 4.5 mmol, 3.0 eq) and the reaction mixture was heated at 80-90 C for 5 h. Solvent was removed and the residue was purified by column chromatography (EtOAc/ MeOH) to give the alkylation product. MS: exact mass calculated for C15H13N303, 283.10; mlz found, 284 [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,10128-72-0, its application will become more common.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102145; (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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile, molecular formula is C6H3ClN2, 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. Product Details of 19235-89-3

Step A Nitrile I (60 g, 0.42 mol) is dissolved in THF (1000 ml) in a 2 l three-necked flask fitted with stirrer and thermometer under an N2 protective-gas atmosphere and cooled to 0 C. by means of an ice bath. Commercially available MeMgl (200 ml of a 3 M solution in THF, 0.6 mmol) is slowly added over the course of about 45 min. A clear, dark solution initially forms. The dropwise addition rate of the MeMgl addition is adjusted so that the solution temperature in the reaction vessel is between 0-10 C. When all the Grignard reagent has been added, a green suspension is obtained, which is stirred at 0 C. for a further 2 h. The reaction mixture is then added to ice-water (1500 ml). 2 M HCl is added until the reaction mixture has an approx. pH2. The mixture is stirred for a further 15 min. and then extracted a number of times (addition of EtOAc and water). The combined organic phases are washed with aqueous saturated sodium chloride solution and dried using Na2SO4. All the solvents are removed by distillation under reduced pressure in a rotary evaporator, giving 66 g of yellow-brown oil as crude product. The crude product is purified by means of column chromatography (800 g of Si60, MTBE). The suitable fractions (characterised by TLC analysis) are combined. Removal of the solvents gives ketone II (51 g, 0.32 mol, 76% yield) as clear dark oil. LC-MS: tR=1.829 min (UV=220 nm), tR=1.842 min. (TIC, with [M+H]+=156); 1H NMR (300 MHz, CDCl3) delta 8.58 (d, 1H), 8.03 (dd, J=2.1, 0.4, 1H), 7.47 (dd, J=5.2, 2.1, 1H), 2.71 (d, J=3.2, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 19235-89-3.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2012/220587; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56673-34-8, 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.56673-34-8, name is 3-Bromo-6-mercaptopyridine, molecular formula is C5H4BrNS, molecular weight is 190.06, as common compound, the synthetic route is as follows.

Weigh 0.591 g of Nd (OTf) 3, 0.33 g of tetraacetylated fucose,0.19 g of 5-bromo-2-mercaptopyridine in a parallel reaction tube. Nitrogen atmosphere were added 10mL1,2-dichloroethane, ionic liquid PFIL-2 [R1, R2, R3 = phenyl,n = 4, X = (CF3SO2) 2N] 0.5mL, the reaction tube was sealed, the reaction was stirred,Microwave irradiation using intermittent, power 500W,Each irradiation for 5 minutes, stop irradiation for 1 minute. Reaction for 5 hours,Temperature control at 80 degrees Celsius. The reaction was terminated by adding water.Separation by silica gel column gave 0.336 g of glycoside 1 in 73% yield.Ionic liquids can be reused, no significant change in yield.

Statistics shows that 56673-34-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-6-mercaptopyridine.

Reference:
Patent; Ningbo University; Chen Weiting; (9 pag.)CN106397507; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153813-70-8, 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 153813-70-8, name is 3-Nitroisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of N-(4-trifluoromethoxyphenyl) 3-aminothiophene-2-carboxamide 3 (302 mg, 1 mmol) in 15 mL ethyl acetate was added 3-nitro pyridine-4-carboxaldehyde 4 (182.4 mg, 1.2 mmol) and trifluoroacetic acid (228 mg, 2 mmol). Sodium borohydride (50 mg,1.3 mmol) was added as a solid over 1 min and the reaction mixture was allowed to stir for 1 h or until the amine was completely consumed as monitored by TLC (n-hexane:EtOAc, 60:40). Sodium hydroxide (10% w/v solution) was added to the reaction mixture to make the solution alkaline (pH 8-9). The phases were allowed to separate and the organic layer was collected, washed with brine, dried over sodium sulfate and concentrated to afford crude yellow product. This crude product was subjected to flash column chromatography (n-hexane:EtOAc, 60:40) to the yield the desired product 5 as a yellow solid (390 mg, 89%). m.p. 130-131 C; TLC (60% n-hexane: 40% EtOAc) Rf = 0.60; 1H NMR (CDCl3, delta ppm): 9.36 (s, 1H, Ar), 8.76-8.77 (d, 1H, J = 5.1, Ar), 8.01-8.04 (br t, 1H, NHCH2), 7.62-7.64 (d, 1H, J= 5.2 Hz, Ar), 7.58-7.60 (d, 2H, J = 8.8 Hz, Ar), 7.26-7.28 (m, 1H, Ar), 7.21-7.23 (d, 2H, J = 8.4 Hz, Ar), 7.12 (br s, 1H, NHCO), 6.48-6.49 (d, 1H, J = 5.4 Hz, Ar), 4.96-4.97 (d, 2H, J = 6.4 Hz, NHCH2); IR (CDCl3, cm-1): 1714, 1363 (-NO2), 1221, 1091, 914, 733, 647; Anal.: Calcd for C18H13F3N4O4S: C, 49.32; H, 2.99; N, 12.78; Found: C, 49.50; H, 3.00; N, 12.81.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 153813-70-8, 3-Nitroisonicotinaldehyde.

Reference:
Article; Patel, Jay P.; Kuang, Ye-Hong; Chen, Zhe-Sheng; Korlipara, Vijaya L.; Bioorganic and medicinal chemistry letters; vol. 21; 21; (2011); p. 6495 – 6499;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 87674-15-5 ,Some common heterocyclic compound, 87674-15-5, molecular formula is C7H8FNO, 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.

Example 2; 2-Bromo-1 -(3«fluoropyridin-4-yl)ethanone hydrobromide; Into a stirred solution of 3-fluoropyridine (14 g, 144.2 rnmol) in anhydrous THF (150 mL), cooled to -780C and under argon, 79.2 mL (158.6 mmol) of a 2N solution of lithiumdiisopropylamsde (LDA) in n-heptane, THF, ethylbenzene, were slowly dropped in about 1h. After stirring for 2.5h a cooled solution (ca. 0DC) of acetaldehyde (8.9 mL, 158.5 mmot) in 25 mL of anhydrous THF was slowly dropped and the reaction mixture was stirred at -78C for 1.5 h. The solution was warmed to -30C and a solution of ammonium chloride (15Og) in 700 mL of water was added. The mixture was extracted with ethylacetate (3 x 400 ml_) and the organic layers were washed with brine (4 x 200 mL) and dried over sodium sulfate. After concentration, the oil was crystallized with n-hexane (40 mL) and 15.6 g (76% yield) of 1-{3- fiuoropyridin-4-yl)ethanol were obtained. A mixture of 1-(3-fiuoropyridin-4-y.)ethanoi (10 g, 70.3 mrnol) and commercial activated MnO2 (8 g, 92.1 mmol) in toluene (100 mL) were refluxed until disappearance of starting material. After cooling, the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3- f.uoro-4-acetyi pyridine (6.9 g, 70%) that was used directly in the next step. To a stirred solution of 3-flu?ro-4-acetyipyridine (5.3 g, 38.1 mmol} in glacial acetic acid (14 mL) and 48% hydrobromic acid (5.3 mL), bromine (2 mL, 38 mmol) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60DC for 2.5 hour. This solution was cooled down and ethylacetate (70 mL) was added. After 30 minutes of stirring, the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtained in 82% yield (9.4 g).1H NMR (DMSOd6 /400 MHz) delta ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (dd, 1 H) 8.81 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87674-15-5, its application will become more common.

Reference:
Patent; PFIZER ITALIA SRL; WO2007/96334; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem