Tag: M.W:200-300

Electric Literature of 117007-52-0, 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 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Under an argon atmosphere, 10 g (40.81 mmol) of 3-iodo-1H-pyrazolo[3,4-b]pyridine (WO 2006/130673, Ex. 4b) and 14.63 g (44.89 mmol) of caesium carbonate were initially charged in 170 ml of N,N-dimethylformamide, and 12.3 g (44.89 mmol) of 1,1,1,2,2-pentafluoro-4-iodobutane, dissolved in 30 ml of N,N-dimethylformamide, were added. The mixture was stirred at room temperature for 2 days. Another 14.63 g (44.89 mmol) of caesium carbonate and 12.3 g (44.89 mmol) of 1,1,1,2,2-pentafluoro-4-iodobutane were then added. The mixture was stirred at room temperature over the weekend, and another 3.49 g (12.72 mmol) of 1,1,1,2,2-pentafluoro-4-iodobutane and 4.14 g (12.72 mmol) of caesium carbonate were added. After a further night at room temperature, 5 g (18.25 mmol) of 1,1,1,2,2-pentafluoro-4-iodobutane and 5.95 g (18.25 mmol) of caesium carbonate were added. After 6 days of stirring at room temperature, the mixture was heated at 70 C. for 2 days. The mixture was then cooled and filtered and the residue was washed with N,N-dimethylformamide. The filtrate was concentrated and purified by preparative HPLC (gradient 0.1% formic acid in water/60-90% methanol. This gave 5.48 g (34% of theory) of the title compound. LC-MS (Method 1): Rt=1.23 min; MS (ESIpos): m/z=392 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta [ppm]=2.85-3.02 (m, 2H), 4.81 (t, 2H), 7.33 (dd, 1H), 7.98 (dd, 1H), 8.65 (dd, 1H).

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 117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Griebenow, Nils; Lang, Dieter; Wunder, Frank; Huebsch, Walter; Vakalopoulos, Alexandros; Tersteegen, Adrian; US2014/357637; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59717-96-3 ,Some common heterocyclic compound, 59717-96-3, molecular formula is C11H8BrNO, 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.

Palladium acetate (315 mg, 1.4 mmol), X-PHOS (1.3 g, 2.8 mmol),Dissolved in 10ml 1,4-dioxane, N2 protected at room temperature for 20min, 5-bromo-2-phenoxypyridine (7 g, 28 mmol) was dissolved in 100 ml of 1,4-dioxane.Add bis(pinacolato)diboron(14.42 g, 56 mmol), potassium acetate (8.4 g, 84 mmol),The activated ligand solution is added thereto, and the N2 is protected at 90 C for 12 hours.After completion of the reaction, the diatomaceous earth was filtered under hot water, and the solvent was evaporated under reduced pressure.Obtained white solid 4.24g, yield 51%,The elution system was petroleum ether: ethyl acetate = 100: 1 – 40:1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59717-96-3, its application will become more common.

Reference:
Patent; Shandong University; Zhao Guisen; Ran Fansheng; Liu Meixia; Liu Yang; Wang Luhua; (48 pag.)CN109369654; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4487-59-6, 2-Bromo-5-nitropyridine, 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: 2-Bromo-5-nitropyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Bromo-5-nitropyridine

To a stirred solution of 2-bromo-5-nitro-pyridine (2.9 g) and N-terbutyloxycarbonyl-piperazine (3.2 g) in DMF (100 mL) was added potassium carbonate (1.98 g). The mixture was heated at 80 C. during 1 hour and then concentrated. The residue was taken in CH2Cl2 and the organic phase was washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The titled compound was obtained as a yellow solid (4.4 g). [0253] m.p.: 169 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4487-59-6, 2-Bromo-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Dodic, Nerina; US2004/9988; (2004); 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. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate. A new synthetic method of this compound is introduced below., Safety of Methyl 5-bromo-2-chloronicotinate

A suspension of zinc (5.0g) in 4N HCl (10mL) was stirred at 30C for 10min and then filtered. The residue was crushed to yield fine particles and then washed with water (5¡Á) and acetone (2¡Á). The activated zinc was then dried in vacuo for 24h. (0020) A solution of 3-chloro-2-flurobenzyl bromide (1.12g, 5mmol) in THF (3mL) was added dropwise to suspension of activated zinc (0.98g, 15mmol), 1,2-dibromoethane (0.034mL, 0.4mmol), trimethylchlorosilane (0.038mL, 0.3mmol) and THF (1.5mL) at 23C. The reaction was heated to 45C and maintained at this temperature for 1.5h. TLC indicated complete consumption of 3-chloro-2-flurobenzyl bromide (sm: Rf=0.4; 30% EtOAc-hexanes). (0021) A solution of (3-chloro-2-fluorobenzyl)zinc bromide in THF (7.98mL, 7.98mmol, 1.0M) was added dropwise over a 10min period to a stirring mixture of 5-bromo-2-chloronicotinate (2.0g, 7.98mmol), tetrakis(triphenylphosphine)palladium (0.923g, 0.798mmol), and THF (26.6mL) at 65C. The resulting mixture was stirred for 1h and then poured into 10% aq. NH4Cl and the layers were separated. The aqueous phase was extracted with EtOAc and the combined organics layers were dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography (10-100% EtOAc-hexanes gradient) to yield the title compound as a yellow oil. (1.8g, 71.8%): 1H NMR (400MHz, CDCl3) delta ppm 8.41 (d, J=2.38Hz, 1H), 7.97 (d, J=2.38Hz, 1H), 7.37-7.29 (m, 1H), 7.08-7.04 (m, 3H), 4.04 (s, 2H), 3.97-3.92 (m, 3H); ES+ MS: 315 (M+1).

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, 78686-79-0, Methyl 5-bromo-2-chloronicotinate.

Reference:
Article; Velthuisen, Emile J.; Johns, Brian A.; Temelkoff, David P.; Brown, Kevin W.; Danehower, Susan C.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 99 – 112;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 83004-10-8, 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.83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

1.05 g (4.19 mmol) of 2-bromo-6-bromomethylpyridine and 2.15 g of potassium carbonate are added to a suspension of 792 mg (3.81 mmol) of 6-(3,5-difluorophenyl)-2H-pyridazin-3-one in 19 ml of acetonitrile, and the mixture is stirred for 18 hours at 80 C. The reaction mixture is filtered and washed with acetonitrile. The filtrate is evaporated and partitioned between tert-butyl methyl ether and water. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent: 2-(6-bromopyridin-2-ylmethyl)-6-(3,5-difluorophenyl)-2H-pyridazin-3-one as yellow crystals; ESI 378, 380.

Statistics shows that 83004-10-8 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-6-(bromomethyl)pyridine.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/34474; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-33-6, 3-Bromo-2-hydroxy-5-nitropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Step 2: To a cooled (0-5 C.) mixture of 3-bromo-2-hydroxy-5-nitropyridine (47 g, 0.214 mol) and quinoline (13.7 g, 0.107 mol) was added POCl3 (26 mL, 0.278 mol) dropwise over ~10 min (the mixture was difficult to stir initially but became less viscous as the reaction progressed and the mixture warmed). After stirring at 120 C. for 3.5 h, the mixture was cooled to 100 C. and water (90 mL) was added. The resulting mixture was stirred vigorously while cooling to 0-5 C. The product was collected by filtration, washed with water and dried in vacuo at 45 C. to give 42 g of 3-bromo-2-chloro-5-nitropyridine (82% yield). 1H NMR (CD3OD) delta 9.19 (d, J=2.4 Hz, 1H), 8.93 (d, J=2.4 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-33-6, 3-Bromo-2-hydroxy-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; US2006/79524; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13959-02-9, 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.13959-02-9, name is 3-Bromoisonicotinic acid, molecular formula is C6H4BrNO2, molecular weight is 202.01, as common compound, the synthetic route is as follows.

Example 64 Synthesis of (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-3-(4-fluorophenoxy)isonicotinamide Compound 35a. To a stirred solution of 3-bromopyridine-4-carboxylic acid (1.0 g, 5.0 mmol, 1 equiv) in DMF (10 mL), was added 4-fluorophenol (0.560 g, 5.0 mmol, 1 equiv), CuI (1.90 g, 10.0 mmol, 2 equiv) and Cs2CO3 (3.260 g, 10.0 mmol, 2 equiv). Heated the reaction mixture at 110 C. for 18 h. Reaction progress was checked by LCMS. The reaction mixture was diluted with water (20 mL) and added few drops of dil. HCl till pH was slightly acidic. The aqueous layer was extracted with ethyl acetate (50 mL*2). Combined organic extracts were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain 3-(4-fluorophenoxy)pyridine-4-carboxylic acid (0.200 g, 18% Yield)

Statistics shows that 13959-02-9 is playing an increasingly important role. we look forward to future research findings about 3-Bromoisonicotinic acid.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1015610-31-7 ,Some common heterocyclic compound, 1015610-31-7, molecular formula is C7H4ClIN2, 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.

In a nitrogen atmosphere, 9H-carbazole (5 g, 29.9 mmol) was dissolved in toluene (70 mL)4-chloro-5-iodo-1H-pyrrolo [2,3-b] pyridine (8.33 g, 29.9 mmol, product number: ADE000983)Tris (diphenylideneacetone) dipalladium (0) (0.27 g, 0.30 mmol),Tris-tert-butylphosphine (0.30 g, 1.50 mmol) and sodium tert-butoxide (3.45 g, 35.9 mmol) were successively added thereto and refluxed by heating at 100 C for 13 hours.After the completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), and the water was removed with anhydrous MgSO 4. The extract was filtered and concentrated under reduced pressure.The thus-obtained residue was purified by flash column chromatography to obtain Compound I-4 (9.03 g, 95%).

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. 1015610-31-7, 4-Chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cheil Industries Co.,Ltd; Lee, Han Ir; Yoo, Eun Sun; Kang, Dong Min; Sin, Ji Hun; Yoo, Dong Kyu; Lee, Sang Sin; Jang, Yoo Na; Jung, Soo Young; Han, Su Jin; Hong, Jin Suk; (46 pag.)KR2015/24669; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, 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, Quality Control of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, blongs to pyridine-derivatives compound. Quality Control of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

Example 74 Production of N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine A mixture of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d] pyrimidine (80 mg), 3-chloro-4- (pyridin-2-ylmethoxy) aniline (94 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140C for 2 hrs, poured into water (10 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate (30 mLx2). The organic layers were combined and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1 ? 0:1). The object fraction was concentrated under reduced pressure. Chloroform – diisopropyl ether was added to the residue, and the solid was collected by filtration and dried under reduced pressure at 60C to give the title compound (71 mg). 1H-NMR (DMSO-d6) delta 5.27 (2H, s), 6.72 (1H, m), 6.78 (1H, d, J= 1.2 Hz), 7.02 (1H, d, J= 3.3 Hz), 7.26 (1H, d, J= 9.0 Hz), 7.36 (1H, m), 7.53-7.59 (2H, m), 7.81 (1H, d, J= 8.1 Hz), 7.91 (1H, s), 8.21 (1H, d, J= 2.4 Hz), 8.34 (1H, s), 8.59 (1H, d, J= 5.1 Hz), 9.19 (1H, br s), 11.62 (1H, br s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 80194-68-9, 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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid. A new synthetic method of this compound is introduced below.

Synthesis of Intermediate Amide Derivatives C14a (R7=COR10) General Procedure A solution of the carboxylic acid (0.3 mmol) in N,N-dimethylformamide (5 ml) was cooled to 0 C. Consecutively, 1-hydroxybenzotriazole hydrate (52 mg, 0.38 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (143 mg, 0.38 mmol), (R)-3-(5-amino-2-fluoro-phenyl)-3-methyl-[1,4]oxazepan-5-one hydrochloride (intermediate C13A) (74 mg, 0.27 mmol), and N-ethyldiisopropylamine (124 mg, 0.94 mmol) were added, and the mixture was stirred at 0 C. for 10 minutes, then left at room temperature for 16 hours. For the workup, the reaction mixture was evaporated to dryness and the residue directly purified by chromatography on a Silicycle-Si-amine column using a gradient of heptane and ethyl acetate as the eluent. Intermediate C14A Starting from 3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid and (R)-3-(5-amino-2-fluoro-phenyl)-3-methyl-[1,4]oxazepan-5-one hydrochloride, the 3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid [4-fluoro-3-((R)-3-methyl-5-oxo-[1,4]oxazepan-3-yl)-phenyl]-amide was obtained as a light yellow foam. MS (ISP): m/z=446.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Banner, David; Guba, Wolfgang; Hilpert, Hans; Humm, Roland; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Rogers-Evans, Mark; Rombach, Didier; Woltering, Thomas; Wostl, Wolfgang; US2011/312937; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem