Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 884494-45-5, 2-Fluoro-4-iodo-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, 884494-45-5, blongs to pyridine-derivatives compound. COA of Formula: C6H5FIN

To a solution of 2-fluoro-4-iodo-6-methylpyridine (800 mg, 3.38 mmol, CAS 884494-45-5) and (S)-l,3-dihydrospiro[indene-2,4′-piperidin]-l-amine (1.11 g, 4.05 mmol, Intermediate I, 2HC1) in NMP (10.0 mL) was added DIPEA (2.35 mL, 13.50 mmol) at 25 C, then the mixture was stirred at 120 C for 24 h. Then, additional (S)-l,3- dihydrospiro[indene-2,4′-piperidin]-l-amine (464 mg, 1.69 mmol, Intermediate I, 2HC1) and DIPEA (1.18 mL, 6.75 mmol) were added with stirring at 120 C for 3 h. Next, (Boc)20 (1.10 g, 5.06 mmol, 1.16 mL) was added to the mixture with stirring, then the reaction was stirred at 25 C for 12 h. The reaction mixture was poured into water (100 mL), and then the aqueous phase was extracted with ethyl acetate (100 mL x 2). The combined organic phase was washed with brine (100 mL x 3), dried over Na2S04, filtered and concentrated in vacuo. The crude product was purified by column chromatography (100-200 mesh silica gel, petroleum ether/ethyl acetate=l00/l to 20/1, Product Rf = 0.48) to afford tert-butyl (S)-(l ‘-(4- iodo-6-methylpyridin-2-yl)-l,3-dihydrospiro[indene-2,4’-piperidin]-l-yl)carbamate (860 mg, 49% yield) as a yellow solid. LC-MS (ESI+) m/z 520.1 (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,884494-45-5, its application will become more common.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 639091-75-1 ,Some common heterocyclic compound, 639091-75-1, molecular formula is C12H16N2O4, 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.

Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaCl2 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight at ambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaCl (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,639091-75-1, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; GOETSCH, Liliane; JOUHANNEAUD, Alexandra; PEREZ, Michel; (129 pag.)WO2016/173682; (2016); 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-2-chloro-4-methoxypyridine

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

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, 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alexander; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda, K.; SUZUKI, Takao; WO2015/100147; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-78-9 ,Some common heterocyclic compound, 69045-78-9, molecular formula is C6H3Cl4N, 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.

REFERENCE EXAMPLE 1 A reaction was conducted for 12 hours in the same manner as in Example 1 except that 2-chloro-5-trichloromethylpyridine (0.2 mole) was replaced by 3-trichloromethylpyridine (0.2 mole). The resulting reaction mixture was analyzed by gas chromatography, which indicated that the amount of 3-cyanopyridine formed was 1% or less.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-78-9, its application will become more common.

Reference:
Patent; Ihara Chemical Industry Co., Ltd.; US5675012; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90145-48-5, 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 90145-48-5, name is 5-Bromopyridine-2-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-1-isopropyl-3-methyl-1H-pyrazol-4-yf)-3-methyl-8-(4,4 5,5-tetramethyl- (1 ,3,2]dioxaborolan-2-yl)-1,3-d.hydroimidazo[4,5-c]quinolin-2-one (Stage 112.1.1 , 34 mg, 0.075 mmol), delta-bromo-py?dine^-carboxylic acid amide (Combi-Blocks, San Diego, USA, 20 mg, 0 099 mmol), and PdCI2(PPh3)2 (3.5 mg, O 005 mmol) in DMF (O 9 ml) and 1 M aqueous K2CO3 (0.187 ml) was stirred under argon at 105 C for 2.5 h The RM was cooled to rt. The mixture was diluted with MeOH + 3 drops TFA and purified directly by Prep.HPLC (H2O (0.1% TFA)/CH3CN 97:3 to 55:45). The fractions containing product were collected together and basifted with NaHCO3 (0.3 g), before being concentrated The resulting layer was extracted with DCM, washed with brine, dned over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (HPLC: tR 2.44 mm (Method A): M+H ~ 442 MS-ES; 1H-NMR (dbeta-DMSO, 400 MHz) 9.00 (s, 1H). 8 75-8 69 (m, 1H), 8.24-8.19 (m, 1H), 8.18-8.07 (m, 2H) 8.07-7.98 (m, 3H), 7.75-7.67 (m, 1 H), 7 61-7.56 (m, 1H)1 4.61-4 48 (m, 1H). 3.58 (s, 3H), 1 97 (s, 3H), 1.45 (s, 3H), 1.43 (s, 3H)).

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 90145-48-5, 5-Bromopyridine-2-carboxamide.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1018505-59-3, 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. 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, 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.

A mixture of impure 5-(4-ethylpiperazin- 1 -yl)pyridin-2-amine (1.00 g, 4.85′ mmol assumed), 8-bromo-6-chloroimidazo[l ,2-a]pyridine hydrochloride salt (1.30 g, 4.85 mmol), 2,2′-bis(diphenylphosphino)-l,r-binaphthalene (634 mg, 1.02 mmol) and cesium carbonate (4.90 g, 15.0 mmol) in toluene (50 mL) was sparged with nitrogen while stirring for 10 min. Palladium(II) acetate (120 mg, 0.491 mmol) was then added and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted in a mixture of 1 : 1 methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1 : 19 methanol/methylene chloride to 1 :6methanol/methylene chloride) to afford 6-chloro-Ar-(5-(4-ethylpiperazin-l-yl)pyiidin-2- yl)imidazo[l,2-a]pyridin-8-amine as a yellow-green solid: NMR (400 MHz, DMS0- )d 9.12 (s, 1H), 8.30 (d, J = 2.0 Hz, 1H), 8.26 (d, J = 2.0 Hz, 1H), 7.99 (d, J = 2.8 Hz, 1 H), 7.89 (d, J = 0.8 Hz, 1H), 7.55 (d, J= 0.8 Hz, 1H), 7.43 (dd, J = 8.8, 2.8 Hz, 1H), 7.35 (d, J= 8.8 Hz, 1H), 3.11-3.10 (m, 4H), 2.50-2.49 (m, 4H, merged with DMSO peak), 2.38-2.37 (m, 2H), 1.04 (t, J= 7.2 Hz, 3H).

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter; CURRIE, Kevin, S; KROPF, Jeffrey, E.; LEE, Seung, H.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; XU, Jianjun; ZHAO, Zhongdong; WO2011/112995; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 727356-19-6, 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 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-((6-Bromopyridin-2-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H- imidazo[2,1-b][1 ,3,6]oxadiazocine (7.2.18)A solution of 2-bromo-6-(chloromethyl)pyridine (1 .0 g, 5.05 mmol) in acetone (50 ml) was treated with sodium iodide (3.8 g, 25.2 mmol). The mixture was refluxed for an hour, potassium carbonate (4.2 g, 30.3 mmol) was added to the reaction. 9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1 – b][1 ,3,6]oxadiazocine, 7.1.3 (1 g, 5.05 mmol) was dissolved in acetone and added to the mixture and stirred overnight. The reaction mixture was filtered and evaporated. The crude was dissolved in a mixture of ethyl acetate and methanol (95%:5%) and filtered through a pad of silica. The silica was washed a few times with the ethyl acetate and methanol mixture. The washings were combined and the solvent evaporated to yield 4-((6- bromopyridin-2-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1 – b][1 ,3,6]oxadiazocine (1 .7 g, 4.6 mmol, 92 %) with 68 % purity. The sample was further purified using prep HPLC. See Table 19 for analytical data.

According to the analysis of related databases, 727356-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ITHEMBA PHARMACEUTICALS (PROPRIETARY) LIMITED; MUSONDA, Chitalu, Christopher; EDLIN, Christopher, David; BOYLE, Grant, Alexander; WO2013/72903; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 936342-91-5, Adding some certain compound to certain chemical reactions, such as: 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride,molecular formula is C6H6BrCl2N, 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 936342-91-5.

5-bromo-2-chloromethyl-pyridine (243mg, 2mmol) and N- isobutyryl piperazine (289mg, 3mmol) was dissolved in the N, N- dimethylformamide (10ml), followed by addition of potassium carbonate ( 691mg, 10mmol), stirred at room temperature for 12 hours, 100ml of water was added to the reaction mixture was cooled, (50ml * 3) and extracted with ethyl acetate, then with saturated sodium chloride solution (100ml * 2) washing the resulting organic phase dried over anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure to give 1- [4- (5-bromo – pyridin-2-ylmethyl) – piperazin-1-yl] -2-methyl – propan-1-one ( 282mg, oil), yield: 86%.

According to the analysis of related databases, 936342-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI CDYMAX PHARMACEUTICALS CO., LTD; An, Xiaoxia; Bie, Pingyan; Liu, Jun; Yang, Wuli; (42 pag.)CN103360407; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 109613-97-0, 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. 109613-97-0, name is 2-Bromo-4-methoxypyridin-3-amine, molecular formula is C6H7BrN2O, 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.

To a solution of 2-bromo-4-methoxy-pyridin-3-ylamine (540 mg, 2.66 mmol) in pyridine (20 mL) at 0 C is added ethyl chloroformate (0.38 mL, 3.99 mmol). After 30 min, more chloro formate is added (~18 mmol) is added until the reaction goes to completion. The mixture is partitioned between sat. NaHC03 and EtOAc. The two layers are separated, and the aqueous layer is extracted with EtOAc once. The combined organic layers are washed with H20 and brine, dried over MgS04, filterd, and concentrated in vacuo. The crude material is purified on silica gel with EtOAc/MeOH (100/0 to 90/10) as eluant to yield 0.54 g of the product as a white crystalline solid. 1H NMR (CDC13, 300 MHz) 8.18 (d, J= 5.6, 1H), 6.84 (d, J= 5.7, 1H), 6.02 (br s, 1H), 4.23 (q, J = 7.0, 2H), 3.92 (s, 3H), 1.31 (t, J= 7.2, 3H). LC Rt: 1.89 min; LCMS m/z 275 (M+l, 100%).

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 109613-97-0, 2-Bromo-4-methoxypyridin-3-amine.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/78984; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 29241-65-4, 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.29241-65-4, name is 5-Bromo-2-chloronicotinic acid, molecular formula is C6H3BrClNO2, molecular weight is 236.45, as common compound, the synthetic route is as follows.

Add 25g Compound 1 to 75ml methanol,Cool to 0 , add 62.89g thionyl chloride dropwise,After the drop, the temperature is raised to room temperature for 2d;Sampling LCMS, the raw materials are basically reacted, most of the methanol is distilled off,The residue was poured into ice water, extracted with EA, the organic phases were combined, washed with salt, dried,Spin to dry to obtain 22.7g crude product.The crude product is directly invested in the next step.

The chemical industry reduces the impact on the environment during synthesis 29241-65-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Changsen Pharmaceutical Co., Ltd.; Wang Zhe; Zhang Jiyong; Zeng Zhihong; (105 pag.)CN111039942; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem