Tag: M.W:200-300

Electric Literature of 83664-33-9, Adding some certain compound to certain chemical reactions, such as: 83664-33-9, name is 2-(Benzyloxy)-5-bromopyridine,molecular formula is C12H10BrNO, 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 83664-33-9.

n-Butyl lithium (2. 5M, 95. 9 mmol, 38. 4 mL, 1. 05 eq.) was added dropwise via syringe to a stirred solution OF 2- (BENZYLOXY)-5-BROMOPYRIDINE (91. 3 mmol, 24. 1 G, 1. 0 eq.) in THF (260 mL, c = 0. 35) cooled to-78 C. Upon completion of addition, the solution was allowed to continue stirring at the same low temperature for 1 hour. At this point, NN-dimethylformamide (183 mmol, 13. 4 G, 2. 0 eq.) was added dropwise as a solution in 5 mL THF. Stirring was continued at the same low temperature for a further 30 minutes at which point the reaction was quenched by addition of 5% sodium bicarbonate. The mixture was transferred to a separatory funnel and extracted with ether (3 x 250 mL). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant yellow oil was purified on a Biotage Sp4 65i over a gradient OF 0-50% hexanes in ethyl acetate to afford the title compound (14. 1 g, 73%). LRMS : 214 (M+H) +. ‘H NMR (DMSO-D6, 400 MHz) ; 10. 02 (1 H, s) 8. 86 (1 H, s) 8. 03 (1 H, d, J=9. 3 Hz) 7. 31-7. 43 (5 H, m) 6. 50 (1 H, d, J=9. 3 HZ) 5. 33 (2 H, s)

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. 83664-33-9, 2-(Benzyloxy)-5-bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2004/92145; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1 ,Some common heterocyclic compound, 1111637-74-1, molecular formula is C7H5BrFNO, 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.

Preparation of (ii^-iV-il-iS-bromo-Z-fluoropyridin-S-y ethylideneJ-Z-methylpropane- 2-sulfinamide (25A). A mixture of l-(5-bromo-2-fluoropyridin-3-yl)ethanone (prepared according to procedures described in WO2009016460; 11.0 g, 50.5 mmol), (i?)-2-methylpropane-2- sulfinamide (AK Scientific, 12.2 g, 101 mmol) and titanium(IV) ethoxide (Aldrich, 26.1 mL, 126.0 mmol) in THF (100 mL) was heated at reflux for 2 hours. The mixture was cooled to room temperature, and brine (200 mL) was added. The suspension was vigorously stirred for 10 minutes. The suspension was then filtered through a pad of silica gel and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SC>4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (gradient 0-20% EtOAc/hexanes) to afford (i?,Z)-N-(l-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (25A) as a bright yellow oil ( 16 g, 99% yield). MS m/z = 320.8 (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,1111637-74-1, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BOURBEAU, Matthew, P.; BROWN, James, A.; CHEN, Ning; FROHN, Michael, J.; LIU, Longbin; LIU, Qingyian; PETTUS, Liping, H.; QIAN, Wenyuan; REEVES, Corey, M.; SIEGMUND, Aaron, C.; (509 pag.)WO2017/24180; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Bromo-2-chloro-6-picoline

General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-chloropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Article; Anchan, Kavitha; Baburajan, Poongavanam; Puttappa, Nagaswarupa H.; Kumar Sarkar, Sujit; Synthetic Communications; vol. 50; 3; (2020); p. 348 – 360;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915107-31-2 ,Some common heterocyclic compound, 915107-31-2, molecular formula is C8H8ClNO3, 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.

3- (4- (Trifluoromethyl) phenyl) pyrrolidine (210 mg, 0.98 mmol) , methyl 6-chloro-5-methoxynicotinate (192 mg, 0.95 mmol) and K 2CO 3 (386 mg, 2.79 mmol) were dissolved in DMSO (6 mL) , and the mixture was heated to 100 and stirred for 5 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (60 mL) , and washed with water (15 mL) and saturated aqueous NaCl (15 mL×5) successively, dried over anhydrous Na 2SO 4 , and concentrated in vacuo to give a crude product, which was purified by silica-gel column chromatography (eluent: PET/EtOAc (v/v) = 5/1) to give a light yellow solid (280 mg, 75%) . [0690] MS (ESI, pos. ion) m/z = 381.2 [M+1] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,915107-31-2, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHONG, Xue; WANG, Feng; LI, Xuke; HE, Wei; PAN, Wei; HUANG, Jiuzhong; ZHANG, Yingjun; ZHENG, Changchun; (0 pag.)WO2020/11147; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 25813-25-6, name is 3,5-Dibromopyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3,5-Dibromopyridin-4-ol

3,5-dibromopyridin-4-ol (239) (1.00 g, 3.95 mmols) was combined with phosphoryl chloride (921.45 mul, 9.89 mmols) in a pressure stable vessel. The vessel was closed and the solution heated to 140 C under stirring for 2.5 h. Afterwards the reation vessel was cooled down to rt and the reaction solution combined with ice cold water (75 mL). The aqueous layer was extracted with EtOAc (5 x 15 mL) and the combined organic layers were dried over anhydrous magnesium sulfate. The product was dried in vacuo. Purification of the crude was performed by silica gel column chromatography (1% EtOAc/n-pentane) to obtain the product (805 mg, 2.97 mmols, 75%) as a white solid. Rf: 0.32 (5% EtOAc/PE). 1H NMR (500 MHz, CDCl3) delta = 8.63 (s, 2H). 13C NMR (126 MHz, CDCl3) delta = 150.97, 144.13, 121.93. GC-MS: tR = 4.59 min; m/z = 268.8, 270.8, 272.8, 274.8 [M ]+. HRMS (ESI): calculated for C5H3N 79Br2 35Cl: m/z = 269.83153 [M+H]+, found: m/z = 269.83155 [M+H]+. calculated for C5H3N 79Br2 37Cl: m/z = 271.82858 [M+H]+, found: m/z = 271.82878 [M+H]+. calculated for C5H3N 79Br 81Br 37Cl: m/z = 273.82653 [M+H]+, found: m/z = 273.82597 [M+H]+. calculated for C5H3N 81Br2 35Cl: m/z = 275.82449 [M+H]+, found: m/z = 275.82316 [M+H]+.

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, 25813-25-6, 3,5-Dibromopyridin-4-ol.

Reference:
Article; Robke, Lucas; Rodrigues, Tiago; Schroeder, Peter; Foley, Daniel J.; Bernardes, Goncalo J.L.; Laraia, Luca; Waldmann, Herbert; Tetrahedron; vol. 74; 35; (2018); p. 4531 – 4537;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 144584-32-7, 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 144584-32-7 as follows.

Example 31 2-Chloro-3-bromo-4-(cis-4-tert-butylcyclohexylamino)pyridine 2.2 g (10 mmol) of 2,4-dichloro-3-bromopyridine, 1.86 g (12 mmol) of cis-4-tert-butylcyclohexylamine and 0.1 g ammonium chloride are warmed at 120 C. for 8 hours in 10 ml of N-methylpyrrolidone. After cooling, saturated aqueous sodium hydrogencarbonate solution is added and the reaction product extracted with ethyl acetate. Purification is carried out by column chromatography. Yield: 1.28 g (37%); RF: 0.41 (diisopropyl ether); 1 H-NMR (CDCl3) delta 7.92 (d, 1H), 6.38 (d, 1H), 5.27 (d, 1H), 3.74 (m, 1H), 1.0-2.0 (m, 9H), 0.89 (s, 9H) ppm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,144584-32-7, its application will become more common.

Reference:
Patent; Hoechst Schering AgrEvo GmbH; US5877322; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 685115-77-9, 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 685115-77-9, name is 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (100 mg, 0.36 mmol) and hydrogen peroxide. urea complex (72 mg, 0.77 mmol) in CH2Cb (2 ml.) cooled to 0 0C was added trifluoroacetic anhydride (0.10 ml_, 0.73 mmol). After 30 min the solution was warmed to r.t, after a further 16 hours a saturated solution of Na2S2Os (10 ml.) was added. The mixture was extracted with CH2CI2 (2 x 20 ml_), the combined organic extracts were washed with a saturated solution of NaHCOs (20 ml_), brine (20 ml_), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2CI2/Me0H, 98:2) to furnish the title compound as a white solid (20 mg, 19%), m.p. 130-133 0C; umax (CHCI3)/ cm”1 3026. 2855, 1724, 1452, 1273, 1 107.

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 685115-77-9, 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 866775-18-0, 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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 mL); Sodium hydroxide (2.0 M aqueous solution) (14.04 mL, 28.1 mmol) was added and the suspension was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in water (100 mL) and then acidifed by the addition of 5.0M HCI(aq). The product was extracted into ethyl acetate (2 x 75 mL) and the combined organic extracts were washed with water (50 mL), brine (25 mL), dried (MgS04) and concentrated in vacuo to afford the title product as a yellow solid. H-NMR: [400MHz, DMSO-d6] ? 13.24 (1 H, br s, C02H), 7.74 (1 H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1 , 287.1 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 866775-18-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUTLER, Rebecca; COLLINGWOOD, Stephen, Paul; HALL, Edward, Charles; EDWARDS, Lee; LEGRAND, Darren, Mark; SPIEGEL, Katrin; WO2013/38386; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13626-17-0, 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. 13626-17-0, name is 3,5-Dibromo-4-chloropyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 3,5-dibromo-4-chloropyridine (X, 0.5 g, 1.84 mmol) and cyclopropylboronic acid (0.17 g, 2.02 mmol), cesium carbonate (1.19 g, 3.68 mmol ) in the mixture of 1,4-dioxan (10 mL) and water (2 mL).The reaction mass was purged with nitrogen for 15 min. Then catalyst Pd (dppf)2Cl2 (0.075 g, 0.09 mmol) was added and allowed to stir at 100 C for 4 h. The reaction mixture was filtered through celite bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts were concentrated under vacuum to afford the crude compound, which was purified by column chromatography using 10-40% ethyl acetate/hexane as an eluent to obtain title compound. MS (M+l): 233.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13626-17-0, 3,5-Dibromo-4-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 619331-71-4, name is 4,7-Dibromo-1H-pyrrolo[2,3-c]pyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C7H4Br2N2

A mixture of 4,7-dibromo-lH-pyrrolo[2,3-c]pyridine (207 mg, 0.75 mmol), 1- tetrahydropyran-2-yl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazole (250 mg, 0.90 mmol), (63 mg, 0.076 mmol), and K2CO3 (0.94 mL, 1.9 mmol, 2.0 M) in DMF (4.0 mL) was stirred at 60 C for 24 h under argon. After cooling, the solvent was evaporated and the residue was chromatographed on a silica gel column (ethyl acetate in dichloromethane 0-100%) to provide 4-bromo-7-(l-tetrahydropyran-2-ylpyrazol-4-yl)-lH-pyrrolo[2,3-c]pyridine (229 mg, 88%). LC-MS 347.1, 349.1 [M+H]+, RT 0.98 min.

The synthetic route of 619331-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; BHATTACHARYYA, Anuradha; JIANG, Yao; KARP, Gary, Mitchell; NARASIMHAN, Jana; TURPOFF, Anthony; ZHANG, Nanjing; (0 pag.)WO2020/5882; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem