Tag: M.W:200-300

Electric Literature of 524955-09-7, 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 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows.

0.500 g (2.14 mmol) of 3-chloro-4-(pyridin-2-ylmethoxy)aniline, 0.317 g (2.14 mmol) of 2,4-dichloropyrimidine, 0.499 g (4.28 mmol)Triethylamine and 5 mL of ethanol were added to the reaction flask and refluxed at 79 C for 6 h.After the reaction, it was cooled to room temperature. The solvent was removed by steaming under reduced pressure.Add 10mL of water,Extract with ethyl acetate (3 x 15 mL) and combine the organic phases.The organic phase is dried over anhydrous sodium sulfate and concentrated.Separated by silica gel column chromatography (dichloromethane: ethyl acetate = 1:20, V/V).Obtained as a pale yellow solid 2-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)-4-chloropyrimidine0.496 g, the yield is 67%.

According to the analysis of related databases, 524955-09-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shaanxi Normal University; Li Baolin; Hao Yunxia; Zhang Yaling; Li Xiabing; Wang Wei; (22 pag.)CN109516959; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 800401-67-6, Adding some certain compound to certain chemical reactions, such as: 800401-67-6, name is Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate,molecular formula is C10H9ClN2O2, 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 800401-67-6.

Step 3: synthesis of ethyl 5-chloro-l-(4-fluorobutyl)-lH-pyrrolo[2,3-c]pyridine-2- carboxylate 10-cTo a solution of ethyl 5-chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylate 10-b (1.9 g, 8.458 mmoles) in acetonitrile (85 mL) was added cesium carbonate (3.306 g, 1.2 eq). This mixture was stirred at room temperature for one hour and then l-bromo-4- fluorobutane (1.089 g, 1.2 eq) was added and stirring at 60C continued overnight. The reaction mixture was filtered over a glass filter and the filtrate was evaporated to dryness. The residue was taken up in dichloromethane and washed with water twice. The organic layer was dried over MgS04, filtered and evaporated. The residue was recrystallised from diisopropylether. The crystals were collected by filtration and dried in vacuo to give 2.19 g (87% yield) of the targeted compound 10-c. m/z = 299 (M+H)+.

According to the analysis of related databases, 800401-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80450; (2012); A1;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 849937-96-8, 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.849937-96-8, name is 5-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.8861, as common compound, the synthetic route is as follows.

To a stirred solution of 5-bromo-2,4-dichloropyridine (3.0 g, 13.22 mmol),isopropylamine (1.7 mL, 19.83 mmol), and Hunig?s Base (11.6 mL, 66.1 mmol) in DMF(5 mL) at room temperature was then heated at 120 C behind a safety shield for 4 hours,at which point it was judged to be complete by LCMS. The reaction mixture was diluted with ethyl acetate and washed 10% LiC1 (3x). The organic layer was dried over Na2SO4, filtered and concentrated to afford the crude product. The product was purified by column chromatography (hexanes/EtOAc) to afford 5 -bromo-2-chloro-N-isopropylpyridin-4-amine (1.29 g, 37% yield) as a colorless oil. LCMS m/z 249.0 (M+H).

Statistics shows that 849937-96-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2,4-dichloropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUNCIA, John V.; GARDNER, Daniel S.; HYNES, John; MACOR, John E.; SANTELLA, Joseph B.; WU, Hong; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; SARKUNAM, Kandhasamy; SISTLA, Ramesh Kumar; POLIMERA, Subba Rao; (72 pag.)WO2016/210037; (2016); A1;,
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Pyridine | C5H5N – PubChem

Application of 573675-25-9, 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. 573675-25-9, name is 5-Bromo-3-nitropicolinonitrile, molecular formula is C6H2BrN3O2, 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 asolution of tetrabutyl-ammonium fluoride (TBAF, 51.2 g, 197.4 mmol, 1.5eq) in DMF (100 mL), 4 A Molecular sieves powder (30 g) were added. The resulting mixture was stirred for 30 minutes. The mixture was filtered and the filtrate was transferred into a 1000 mL reaction flask. A solution of compound 88 (30 g,131.6 mmol, l .Oe q) in DMF (50 mL) was added to the above solution via a addition funnel over 10 minutes, while maintaining the internal temperature below -15C. After stirring for 20 minutes, 2 N HC1 (60 mL) was added over 5 minutes. After aging for1 hour, the mixture was cooled to 2.5C and filtered. The filtration cake was washed by DMF/water (10% (v/v), 2 x 36 mL). The filtrate was combined and concentrated in vacuo. The resulting residue was re-crystallized from 2-propanol (50 mL) to afford the desired compound 89 (13 g).

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 573675-25-9, 5-Bromo-3-nitropicolinonitrile.

Reference:
Patent; TIBOTEC PHARMACEUTICALS; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2012/13643; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113975-22-7, 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. 113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, 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.

Example 5 – 2,2′-Difluoro-4,4′-diiodo-3,3′-bipyridine (5a) 2-Fluoro-3-iodopyridine (7.80 mmol, 1.74 g) was dissolved in 40 ml of anhydrous THF under nitrogen atmosphere and the solution was cooled in acetone/C02 bath. LDA (1.1 eq., 1.2 M in hexanes-THF, 8.58 mmol, 7.15 ml) was added dropwise. The reaction mixture became yellowish and after stirring for 0.5h it was analyzed by GC/MS. A clean BCHD reaction was confirmed, the mixture was stirred for additional 0.5h and CuCl2 (1.1 eq., 8.58 mmol, 1.15 g) was added in one portion. The yellow reaction mixture became dark blue, then brown red (within 1-2 h) and then light greenish after warm up to room temperature. The reaction mixture was treated with hexanes and water, the organic phase was removed, and the aqueous phase was extracted with hexanes (2 x -20 ml). The combined organic phases were dried over MgS04 and the solvent was removed by rotary evaporation to give greenish- brownish oil which partially solidified on standing. This crude product was purified by column chromatography (200 ml of silica gel, hexanes :CH2C12 mixtures (2: 1, 1 : 1 : and then 1 :2) as eluants). The solvents were removed from combined fractions and the product was obtained as off-white solid (1.04 g, 60.1%). UV-vis (CH2C12) max, nm226, 244, 268. HRMS (EI) calculated for Ci0H4F2I2N2 443.8432; found 443.8417. 1H NMR (CDC13, 400 MHz): delta 8.01 (d, J= 5.2 Hz, 2H), 7.82 (d, J= 5.2 Hz, 2H); 13C{1H} NMR (CDCI3, 100 MHz): delta 159.28 (d, J (C-F) = 242.8 Hz, quaternary C), 148.5 (d, J(C-F) = 15.62 Hz, CH), 132.1 (d, J(C-F) = 4.6 Hz, CH), 125.0 (dd, J (C-F) = 33.4 Hz, 4.1 Hz), 114.5 (d, J(C-F) = 1.7 Hz). Anal. Calc. for Ci0H4F2I2N2: C, 27.05; H, 0.91; N, 6.31. Found: C, 27.52; H, 0.84;

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 113975-22-7, 2-Fluoro-3-iodopyridine.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; GETMANENKO, Yulia A.; MARDER, Seth; HWANG, Do Kyung; KIPPELEN, Bernard; WO2013/23108; (2013); A1;; ; Patent; GEORGIA TECH RESEARCH CORPORATION; GETMANENKO, Yulia A.; MARDER, Seth; HWANG, Do Kyung; KIPPELEN, Bernard; WO2013/23106; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 79456-34-1, 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 79456-34-1, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

8.04 g (31.7 mmol) of 5-bromo-3-trifluoromethyl-pyridin-2-ylamine (preparation see Stage 1.3.2), 10.5 g (41.2 mmol) of 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1 ,3,2]dioxaborolanyl] (Aldrich), 9.62 g (95.1 mmol) of KOAc in 100 ml dioxane are degassed with argon for 15 min. Then 776 mg (0.951 mmol) of bis(diphenylphosphino)ferrocene dichloropalla-dium(ll)di-chloromethane (ABCR) are added and the mixture is degassed for 15 more minutes. The reaction mixture is heated at 1 15C for 8 h. After that time, the reaction mixture is filtered and the solvent evaporated. The residue is purified by simple filtration on silicagel (solvent system: t-butyl-methyl ether-EtOAc-NEt3 = 50:50:0.1 ) to yield the title compound as almost colorless solid. ES-MS: (M+1 ) = 289; TIc: Rf=O.77 in t-buthyl-methyl ether-EtOAc 1 :1.

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 79456-34-1, 5-Bromo-3-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; IMBACH, Patricia; MAH, Robert; STAUFFER, Frederic; WO2010/139747; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 83004-10-8, 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 83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of cyanoacetone sodium salt (CAS: 70807-22-6; 1.53 g; 14.6 mmol) in 8 mL of N,N-dimethylformamide and 240 muL of water is cooled to 0C and 2-bromo-6- (bromomethyl)pyridine (2.44 g; 9.72 mmol) in 8 mL of N,N-dimethylformamide is added dropwise and the reaction is stirred at room temperature overnight. The reaction is concentrated under reduced pressure to provide a crude product, which is used directly in the next step. (0568) Yield: 0.89 g (36 % of theory) (0569) Mass spectrometry (ESI+): m/z = 253/255 [M+H]+ (Br) (0570) HPLC (Method 3): Retention time = 0.87 min

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 83004-10-8, 2-Bromo-6-(bromomethyl)pyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TRIESELMANN, Thomas; GODBOUT, Cedrickx; HOENKE, Christoph; VINTONYAK, Viktor; (130 pag.)WO2019/149660; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 91872-10-5 , The common heterocyclic compound, 91872-10-5, name is 3,5-Dibromo-6-methyl-2-pyridinamine, molecular formula is C6H6Br2N2, 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 245 N-[(3,5-dibromo-6-methylpyridin-2-yl)carbamothioyl]benzamide An acetone solution (14.0 mL) of 2-amino-3,5-dibromo-6-methylpyridine (5.05 g) and benzoyl isothiocyanate (3.25 g) was heated under reflux for 8 h After cooling to room temperature, diisopropy ether was added, and the resulting solid was collected by filtration and dried to give the title compound (6.67 g). MS(ESI)m/z; 428,430,432[M+H]+

The synthetic route of 91872-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; OKUYAMA, Masahiro; FUKUNAGA, Kenji; USUI, Kenji; HAYASHI, Norimitsu; IIJIMA, Daisuke; HORIUCHI, Hideki; FUJIMOTO, Nobuaki; (218 pag.)EP3372601; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131803-48-0 ,Some common heterocyclic compound, 131803-48-0, molecular formula is C8H8BrNO2, 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-ethyl-N-(3-fluorophenyl)piperazine- l-carboxamide (0.334 g, 1.330 mmol) and sodium hydride (60.00 %, 0.059 g, 1.463 mmol) in tetrahydrofuran (6 mL) was stirred at the room temperature for 30 min, and mixed with methyl 6-(bromomethyl)nicotinate (0.337 g, 1.463 mmol). The reaction mixture was stirred at the same temperature for additional 18 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The bi-phasic mixture was passed through a plastic frit to remove the solid residues and aqueous layer, and the organic layer collected was concentrated in vacuo. The title compound was used without further purification (methyl 6-((4-ethyl-N-(3-fluorophenyl)piperazine- l-carboxamido)methyl)nicotinate, 0.530 g, 99.5 %, brown oil).

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. 131803-48-0, Methyl 6-(bromomethyl)nicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90902-83-3, 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. 90902-83-3, name is 3-Amino-2-bromo-5-chloropyridine. A new synthetic method of this compound is introduced below.

tert-Butyl N- [(iS)- 1- [3 -(5,5 -dimethyl- 1,3 ,2-dioxaborinan-2-yl)phenyl]but-3 -en-iyl]carbamate (0.339 g, 0.944 mmol), 2-bromo-5-chloropyridin-3-amine (0.196 g, 0.944 mmol), and 2.0 M aq Na2CO3 (2.36 mL, 4.72 mmol) were added to dioxane (8 ml) and the resulting solution was purged with a stream of Ar for 10 mi Pd(PPh3)4 (0.055 g,0.047 mmol) was added and the mixture irradiated on microwave at 120 C for 30 mm. The reaction was quenched with water (20 ml) and extracted with EtOAc (3 x 30 ml). The combined organic layers were washed with brine (15 ml), dried (Na2SO4), filtered and concentrated. The residue was purified by normal phase chromatography using DCM and 0-10% MeOH as eluents to afford tert-butyl N-[(1S)-1-[3-(3-amino-5-chloropyridin-2-yl) phenyl]but-3-en-1-yl] carbamate (0.375g, 106%) as a tan foam. MS(ESI) m/z: 374.3(M+H). ?H NMR (500MHz, CDC13) oe 8.08 (d, J=2.2 Hz, 1H), 7.60 – 7.52 (m, 2H), 7.48 -7.43 (m, 1H), 7.34 (d, J7.7 Hz, 1H), 7.07 (d, J1.9 Hz, 1H), 5.72 (ddt, J=17.1, 10.1, 7.0Hz, 1H), 5.21 – 5.09 (m, 2H), 4.93 (br. s., 1H), 4.81 (br. s., 1H), 3.94 (br. s., 2H), 2.63 -2.51 (m, 2H), 1.43 (br. s., 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90902-83-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem