Tag: M.W:200-300

Application of 727356-19-6, Adding some certain compound to certain chemical reactions, such as: 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine,molecular formula is C6H5BrClN, 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 727356-19-6.

Compound 7 (0.15 g, 0.57 mmol) was dissolvedin N,N-dimethylacetamide (2 mL) and sodium hydride (0.017 g, 0.7 mmol) added. The mixture was stirred at room temperature for 20 minutes. Then compound 15(0.2 g, 0.77 mmol) was added and the mixture was heated at ~ 60C in a sand-bath for 2 h. The mixture was diluted with ethyl acetate (40 mL) and brine (15 mL).The organic phase was separated, dried over Na2SO4, filtered and the solvents removed. The residue was purified by chromatography on silica using dichloromethane to elute excess benzyl chloride, followed by dichloromethane/acetone (95/5) to afford 18 as yellow oil (0.2 g, 82 %). 1H-NMR (400 MHz, CDCl3): delta= 1.40 (s, 9H), 2.86 (t, 2H), 4.48 (t, 2H), 5.25 (s, 2H), 6.88 (d, 1H), 7.17 (d, 1H), 7.32 (d, 1H), 7.45 (t, 1H), 7.58 (t, 1H), 7.74 (d, 1H).

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:
Article; Kroth, Heiko; Sreenivasachary, Nampally; Hamel, Anne; Benderitter, Pascal; Varisco, Yvan; Giriens, Valerie; Paganetti, Paolo; Froestl, Wolfgang; Pfeifer, Andrea; Muhs, Andreas; Bioorganic and Medicinal Chemistry Letters; vol. 26; 14; (2016); p. 3330 – 3335;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1026796-81-5, 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 1026796-81-5 as follows.

Step 2: N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide To a mixture of N-(4-bromopyridin-2-yl)acetamide (17.2 g, 80 mmol, 1.0 equiv.), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (26.4 g, 104 mmol), Pd(dppf)Cl2 (11.7 g, 16 mmol) and KOAc (23.6 g, 240 mmol) under an atmosphere of nitrogen was added anhydrous DMF (1500 mL). The mixture was allowed to stir at 80 C. for 3.5 h. The solvent was removed and the residue was diluted with EtOAc (1000 mL). Activated carbon (100 g) was added. The slurry was heated at reflux for 5 min and then filtered. The organic solution was concentrated and the residue was re-crystallized from EtOAc to give N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (6.1 g, 29%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 1.29 (s, 12H), 2.09 (s, 3H), 7.24 (dd, J=6.0, 1.2 Hz, 1H), 8.30-8.33 (m, 2H), 10.47 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1026796-81-5, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); 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. 1160791-13-8, name is 2-Amino-6-bromothiazolo[5,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Amino-6-bromothiazolo[5,4-b]pyridine

6-Bromo-[1 ,3]thiazolo[5,4-b]pyridin-2-amine (0.1 g, 0.43 mmol) was dissolved in N-methyl-2-pyrrolidone (1.5 mE) and ethyl 3-bromo-2-oxopropanoate (64 pi, 0.43 mmol) added dropwise. The reaction was stirred at room temperature for 1 hour then heated to 60 C. overnight. The reaction was cooled then water/ice added. The resulting precipitate was isolated by vacuum filtration. The red solid was further dried in a vacuum oven to give the title compound. ?H NMR(500 MHz, DMSO) 9.05 (s, 1H), 8.95 (d, J=2.1 Hz, 1H), 8.74 (d, J=2.1 Hz, 1H), 4.32 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H). Tr(MS10)=1.55 mi mlz (ES(M+H)328, 329

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, 1160791-13-8, 2-Amino-6-bromothiazolo[5,4-b]pyridine.

Reference:
Patent; CHDI Foundation, Inc.; Dominguez, Celia; Wityak, John; Bard, Jonathan; Brown, Christopher John; Prime, Michael Edward; Johnson, Peter David; Krulle, Thomas Martin; Clark-Frew, Daniel; Higgins, Duane; Mills, Matthew Robert; Marston, Richard Waldron; Coe, Samuel; Jones Green, Samantha Louise; Hayes, Sarah; (71 pag.)US2017/56535; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3430-26-0, 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. 3430-26-0, name is 2,5-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

Step A: 5-Bromo-2-iodo-4-methyl-pyridine To a solution of 2,5-dibromo-4-methylpyridine (2 g) in acetonitrile (40 ml) at room temperature under argon were added sodium iodide (4.8 g) then acetyl chloride (0.94 g). After 3 hours stirring at room temperature the white solid formed was filtered off and the filtrate was neutralized with aqueous saturated solution of sodium hydrogenocarbonate. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/cyclohexane) to afford the title product as a brown solid (2.04 g). 1H-NMR (CDCl3, 400 MHz): 8.40 (s, 1H), 7.60 (s, 1H), 2.30 (s, 3H),

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3430-26-0, its application will become more common.

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2012/238517; (2012); 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Bromo-5-chloro-3-nitropyridine

A mixture of 2-bromo-5-chloro-3-nitropyridine (2.8 g; 11.79 mmol) and copper(I) cyanide (1.40 g, 15.63 mmol) in DMF (30 mL)was stirred at 110C for 1.5 h. The mixture was concentrated. The residue was diluted with water (60 mL), extracted three times with EtOAc (50 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by columnchromatography (elution: DCM/Petroleum ether 1/1). The desired fractions were collected and concentrated to give 1.10 g of intermediate 521 (51% yield) as a yellow solid.

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, 75806-86-9, 2-Bromo-5-chloro-3-nitropyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1256810-26-0, 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. 1256810-26-0, name is 6-Bromo-3-methoxypicolinic acid, molecular formula is C7H6BrNO3, 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 mixture of 6-bromo-3-methoxypicolinic acid (3.6 g, 15.52 mmol) and K2CO3 (4.29 g, 31 .0 mmol) in A/,A/-Dimethylformamide (20 mL) was added iodomethane (4.40 g, 31 .0 mmol). The reaction mixture was stirred at 60 C for 4h. The mixture was then poured into water (10 mL) and was extracted with EtOAc (3×30 mL). The combined organic layers were washed by aqueous LiCI (2×30 mL) and brine (50 mL), dried over anhydrous MgS04 and concentrated in vacuum to give crude methyl 6-bromo-3-methoxypicolinate as a clourless gum. Ethyl 2- chloro-2,2-difluoroacetate (7.38 g, 46.5 mmol), potassium fluoride (9.01 g, 155 mmol) and copper(l) iodide (8.86 g, 46.5 mmol) and A/,A/-Dimethylformamide (20.00 mL) were then added and the reaction mixture was stirred at 120 C for 18h. The mixture was cooled to rt and water (30 mL) was added. The mixture was filtered and extracted with EtOAc (3×30 mL). The combined organic layers were washed by aqueous LiCI (2×30 mL) and brine (50 mL), dried over anhydrous MgS04 and concentrated in vacuum to give methyl 3-methoxy-6- (trifluoromethyl)picolinate as a crude product. The crude product was dissloved in methanol (20 mL) and a solution of LiOH (1 .858 g, 78 mmol) in water (20 mL) was added. The reaction mixture was stirred at 40 C for 1 h. The pH was then adjusted to 5 with 1 N HCI. The mixture was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous MgS04 and concentrated under vacuum to give 3-methoxy-6- (trifluoromethyl)picolinic acid (1 .7 g, 6.92 mmol, 44.6 % yield) as a white solid, m/z: [M + H]+ Calcd for C8H7F3NO3 222.0; Found 222

According to the analysis of related databases, 1256810-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 947249-13-0, 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. 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, molecular formula is C6H5BrF2N2O, 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 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 13.39 mmol) in 1,4-dioxane (60 mL) were added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (3.74 g, 14.73 mmol), tricyclohexylphosphine (525 mg, 1.87 mmol), potassium acetate (3.28 g, 33.47 mmol) and tris(dibenzylideneacetone)dipalladium(0) (490 mg, 0.53 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 110 C. for 16 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3*75 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25% ethyl acetate in hexane) affording 3-(difluoromethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.3 g, 34%): 1H NMR (400 MHz, DMSO-d6) delta 8.03 (s, 1H), 7.33 (s, 1H), 7.11 (t, J=73.6 Hz, 1H), 6.44 (s, 2H), 1.25 (s, 12H).

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 947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine.

Reference:
Patent; GENENTECH, INC.; Siu, Michael; Estrada, Anthony; Liu, Wen; Lyssikatos, Joseph P.; Patel, Snahel; Liang, Guibai; Chen, Kevin; US2015/175619; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-70-8 ,Some common heterocyclic compound, 22282-70-8, molecular formula is C5H3FIN, 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 216A 2-Fluoro-4-vinylpyridine A mixture of 2-fluoro-4-iodopyridine (2.23 g, 10.0 mmol), tributyl vinyl tin (3.8 g, 12 mmol), and Pd2Cl2 (PPh3)2 (703 mg, 1.0 mmol) in dioxane (20 mL) was heated under nitrogen at 80 C. overnight. After cooled, ethyl acetate (40 ml) and saturated KF aqueous solution were added to the reaction mixture. The mixture was stirred for 30 min. The organic layer was separated and washed with water, dried (MgSO4), and concentrated. The resulting residue was purified by flash column chromatography eluding with hexane/ethyl acetate (20:1) to provide the title compound (463 mg, 38%). 1H-NMR (500 MHz, CDCl3) delta ppm 5.55 (d, J=10.92 Hz, 1H) 5.99 (d, J=17.47 Hz, 1H) 6.67 (dd, J=17.47, 10.61 Hz, 1H) 6.88 (m, 1H) 7.17 (dt, J=5.30, 1.56 Hz, 1H) 8.16 (d, J=5.30 Hz, 1H).

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. 22282-70-8, 2-Fluoro-4-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1030626-87-9, 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 1030626-87-9 as follows.

A.6 (5-Chloro-fl, 2, 4]triazolo[l, 5-a]pyridin-8-yl)-[4-(4-methyl-piperazin-l-yl)-phenyl] -amine[0333] A solution of 8-bromo-5-chloro-[l,2,4]triazolo[l,5-a]pyridine (100 mg, 0.43 mmol), A-(4-methyl-piperazin- 1 -yl)-phenylamine (91 mg, 0.47 mmol), sodium-tert-butoxide (58 mg, 0.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (39 mg, 40 mumol) and Xantphos (50 mg, 90 mumol) in dioxane is degassed for one minute by nitrogen bubbling and irradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 45 minutes at 110 0C. After addition of dichloromethane the suspension is filtered through a plug of silica and the filtrate evaporated and stripped twice with dichloromethane. The residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5) affording the title compound (95 mg) as a foam.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1030626-87-9, its application will become more common.

Reference:
Patent; GALAPAGOS N.V.; BURRITT, Andrew; WO2008/65198; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 234108-73-7 , The common heterocyclic compound, 234108-73-7, name is tert-Butyl 2-chloropyridine-4-carbamate, molecular formula is C10H13ClN2O2, 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.

A solution of 4-amino-2-chloropyridine (1.28 gm, 10 mmol) and di-tert-butyl dicarbonate (2.21 gm, 10.1 mmol) in THF (20 mL) was cooled to 00C and a solution of IM lithium bis(trimethylsilyl)amide in THF ( 20 mL, 20 mmol) was added slowly maintaining the temperature below 00C. The reaction was allowed to warm to room temperature over one hour and then quenched by the addition of 1.5 N aqueous ammonium chloride (15 mL). After stirring for several hours the reaction was extracted into ethyl acetate, washed with brine, the organic layer dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether give pure tert-butyl (2-chloropyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 25 – 45% ethyl acetate/ hexane to afford more product. EPO A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 gm, 5 mmol) in dry THF (20 mL) was cooled to -700C under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCtheta3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylrhoyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. 1H-NMR(5OO MHz, CDCI3): deltall.O (IH, br s), 10.52 (IH, s), 8.38 (IH, d, J= 6 Hz), 8.31 (IH, d, J= 6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

The synthetic route of 234108-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem