Day: April 6, 2022

Application of 1093879-46-9 , The common heterocyclic compound, 1093879-46-9, name is 2-(6-Bromopyridin-2-yl)acetic acid, molecular formula is C7H6BrNO2, 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.

Step 1 : to a solution of 2-(6-bromopyridin-2-yl)acetic acid (266 mg, 1 .23 mmol) in DMF (5 ml.) were added DMAP (150 mg, 1.23 mmol), EDCl.HCl (279 mg, 1 .35 mmol) and [4-methyl- 2-(piperidin-1 -yl)phenyl](5-methylfuran-2-yl)methanamine Ex.2 (350 mg, 1.23 mmol). The reaction mixture was stirred at rt. After completion of the reaction (monitored by TLC), sat. NH4CI was added and the solution was extracted with EtOAc. The organic layer was washed with sat. NH4CI, dried over MgS04, filtered and evaporated to dryness under reduced pressure. The crude material was purified by column chromatography on silica gel using Cyclohexane/EtOAc (70:30) as eluent to afford 2-(6-bromopyridin-2-yl)-N-{[4-methyl-2- (piperidin-1 -yl)phenyl](5-methylfuran-2-yl)methyl}acetamide (470 mg, 79%) as yellow oil. 1H NMR (300 MHz, DMSO-d6, d in ppm): 1.39-1 .59 (m, 6H), 2.17 (s, 3H), 2.26 (s, 3H), 2.52- 2.63 (m, 2H), 2.73-2.87 (m, 2H), 3.66 (s, 2H), 5.91 (d, 1 H, J=3.3Hz), 5.94 (dd, 1 H, J=3.0Hz, J=0.9Hz), 6.49 (d, 1 H, J=8.4Hz), 6.91 (d, 1 H, J=7.9Hz), 6.95 (s, 1 H), 7.20 (d, 1 H, J=7.8Hz), 7.35 (dd, 1 H, J=7.5Hz, J=0.6Hz), 7.49 (dd, 1 H, J=7.9Hz, J=0.7Hz), 7.68 (t, 1 H, J=7.4Hz), 8.86 (d, 1 H, J=8.4Hz).

The synthetic route of 1093879-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (76 pag.)WO2018/138356; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884494-82-0, 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. 884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid. A new synthetic method of this compound is introduced below.

[0361] To a solution of 5-fluoro-2-methoxynicotinic acid (372 mg, 2.172 mmol) in DCM (18.3 mL) was added oxalyl chloride (380 xL, 4.34 mmol) and DMF (8.41 mu, 0.109 mmol) at 0C. After stirring at 20C for 1 hour, the mixture was concentrated in vacuo. The residue was taken up in THF (1 mL) and added dropwise to a mixture of 5-amino-4-(4-(2,4- difluorophenoxy)piperidin-l-yl)-NJV-dimethylpicolinamide (545 mg, 1.448 mmol) and DIPEA (759 xL, 4.34 mmol) in THF (11 mL). The reaction mixture was stirred at 60C for 1 hour, then cooled to RT, and filtered. The filtrate was purified by HPLC, eluting with ACN in water. The solid product was recrystallized from 3: 1 MeOH/water solution and filtered. The solids were placed in a 70C vacuum oven overnight to give the title compound as an off-white solid (487 mg, 63.5%). NMR (500 MHz, DMSG-cfe) delta ppm 1.81 – 1.87 (m, 2 H), 2.06 – 2.10 (m, 2 H), 2.94 – 2.98 (m, 2 H), 2.99 (d, J=6,83 Hz, 6 H), 3.27 (dd,,1=1.96, 7.08 Hz, 2 H), 4.12 (s, 3 H), 4.55 (di,./ 7.93. 4.09 Hz, 1H), 6.99 – 7.05 (m, 1H), 7.27 – 7.34 (m, 3 H), 8.25 (dd,./ K.54. 3.17 Hz, 1H), 8.46 (d,./ 3.42 Hz, 1H), 9.15 is. 1H), 10.17 (s, 1H); ES1-MS m/z j M 1 .] 530.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-82-0, 5-Fluoro-2-methoxynicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 21427-61-2, 5-Chloro-2-hydroxy-3-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, 21427-61-2, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3ClN2O3

Intermediate 4; 3-amino-5-chloropyridin-2-ol; To a 500 mL round bottom flask charged with 5-chloro-2-hydroxy-3-nitro pyridine (4.9 g, 28.7 mmol), Fe (7.2 g, 129.7 mmol) and CaCI2 (2.86 g, 25.8 mmol) was added 4:1 EtOHiH2O (50 mL) and the mixture was heated at reflux for 2h. After cooling to room temperature the mixture was filtered through a celite pad and washed with ethanol/water. EPO The dark filtrate was evaporated and dried in vacuum for 2h to afford 3-amino-5-chloropyridin- 2-ol. LCMS: m/e 145 (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,21427-61-2, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2006/51410; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 36936-23-9, name is 5-Chloro-6-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Chloro-6-methylpyridin-2-amine

Intermediate IXc 3 ,6-dichloro-2-methylpyridine To a suspension of 5-chloro-6-methylpyridin-2-amine (7.5 g, 52.60 mmol, Combi- Blocks) in DCM (200 niL) was added copper(II) chloride (9.19 g, 68.38 mmol) and stirred at for 10 min. tert-butyl nitrite (12.50 mL, 105.20 mmol) was added and the stirring was continued further 30 min at RT. The colour was changed to dark blue. The reaction was monitored by LCMS. LCMS showed the completion of reaction. The reaction mixture was washed with water, brine solution, and organic layer was dried on sodium sulphate and concentrated under vacuum to get crude. The product was purified by column chromatography using 5 % ethyl acetate :hexane mixture to get 3,6-dichloro- 2-methylpyridine (3.80 g, 44.6 %) as a yellow liquid. MS (ES+), (M+H)+ = 162.15 for C6H5C12N.

With the rapid development of chemical substances, we look forward to future research findings about 36936-23-9.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; HAMEED PEER MOHAMED, Shahul; PATIL, Vikas; MURUGAN, Kannan; VITHALRAO BELLALE, Eknath; RAICHURKAR, Anandkumar; LANDGE, Sudhir; PUTTUR, Jayashree; ROY CHOUDHURY, Nilanjana; SHANBHAG, Gajanan; KOUSHIK, Krishna; IYER, Pravin; KIRTHIKA SAMBANDAMURTHY, Vasan; SOLAPURE, Suresh; NARAYANAN, Shridhar; WO2015/165660; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 880870-13-3, Adding some certain compound to certain chemical reactions, such as: 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine,molecular formula is C6H5BrClNO, 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 880870-13-3.

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged nitrogen for 15 min. Next, 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 95C for 12 h under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0 – 30% ethyl acetate/hexanes to afford the product. 1HNMR (500 MHz, DMSO- 6) delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS: [(M+l)]+ = 169.

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 175204-80-5, 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 175204-80-5, name is 3-Amino-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Oxalylchloride (132 muL, 1.5 mmol) was added dropwise to a stirred suspension ofbenzoic acid 124 (350 mg, 1.0 mmol) and DMF (1 drop) in dry THF (20 mL) and thesolution was stirred at 20 C. for 2 h, then at 66 C. for 1 h. The solutionwas cooled to 20 C., then the solvent was evaporated and the residue dissolvedin dry pyridine (10 mL). 4-Trifluoromethyl-3-pyridinylamine (180mg, 1.1 mmol) was added and the solution stirred at 20 C. for 16 h. Thesolvent was evaporated and the residue suspended in ice/water (50 mL) for 1 h.The precipitate was filtered, washed with water (5 mL) and dried. The crudesolid was purified by column chromatography, eluting with EtOAc, to givebenzamide 140 (265 mg, 53%)

According to the analysis of related databases, 175204-80-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THEBOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLANDUNISERVICES LIMITED; SUTPHIN, PATRICK; CHAN, DENISE; TURCOTTE, SANDRA; DENNY, WILLIAMALEXANDER; HAY, MICHAELPATRICK; GIDDENS, ANNACLAIRE; BONNET, MURIEL; GIACCIA, AMATO; (181 pag.)JP5789603; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

Stage b)1H-Pyrazolo[3,4-b]pyridine-3-carbonitrile; 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (500 mg, 2.67 mmol) is heated in 33% strength aqueous ammonia solution (10 ml) in a microwave at 140 C. for 10 min. The mixture is then concentrated in vacuo, and the residue is stirred with 100 ml of ethyl acetate and 20 ml of tert-butyl methyl ether at 70 C. Insoluble constituents are removed by suction filtration while hot, and the filtrate is concentrated. Drying results in 346 mg (90% of theory) of the title compound as pale beige crystals.1H-NMR (400 MHz, DMSO-d6): delta=7.47 (dd, J=8.2, 4.5 Hz, 1H), 8.46 (dd, J=8.2, 1.5 Hz, 1H), 8.73 (dd, J=4.5, 1.5 Hz, 1H), 15.02 (br. s, 1H).LC/MS (method 1): Rt=1.30 min.; MS (ESIpos): m/z=145 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 956010-87-0.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/113507; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Product Details of 98273-79-1

INTERMEDIATE 22Methyl 3-(3′-ethoxy-3-fluorobiphenyl-4-ylamino)isonicotinate; A mixture of methyl 3-chloroisonicotinate (1.00 g, 5.83 mmol), intermediate 1 (1.35 g, 5.83 mmol), Cs2CO3(2.66 g, 8.16 mmol) and Xantphos (0.68 g, 1.17 mmol) in dioxane (20 mL) was stirred under argon atmosphere for 10 min. Then Pd2(dba)3 (0.53 g, 0.58 mmol) was added and the mixture stirred under argon atmosphere at 12O0C overnight. The reaction mixture was filtered over Celite and washed with CH2CI2. The filtrate was concentrated and purified by column chromatography eluting with EtOAc/hexane/Et3N (20/79/1) and the desired compound was obtained. Yield=51% LRMS: m/z 367 (M+1 )+.1H NMR (250 MHz1 CDCI3) delta ppm: 9.26 (s, 1 H); 8.8 (s, 1H); 8.25 (d, J = 5.3 Hz, 1 H); 7.87 (d, J = 5.3 Hz, 1 H); 7.72-7.45 (m, 4H); 7.3 (d, J = 8.2 Hz, 1 H); 7.26 (s, 1H); 7.05 (dd, J = 8.2, J= 1.8 Hz, 1 H); 4.25 (c, J = 7 Hz, 2H); 4.12 (s, 3H); 1.61 (t, J = 7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2008/77639; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 127446-34-8 ,Some common heterocyclic compound, 127446-34-8, molecular formula is C11H13ClN2O2, 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.

10.i. 7-chloro-3-fluoro-1,8-naphthyridin-2(1H)-one To a solution of N-(6-chloro-3-formylpyridin-2-yl)pivalamide (prepared as described in J. Org. Chem. (1990), 55, 4744; 3.0 g, 12.64 mmol) in MeCN (250 mL) was added triethyl 2-fluoro-phosphonoacetate (4 g, 16.51 mmol), lithium chloride (0.935 g) and DBU (2.8 mL, 18.7 mmol). The mixture was stirred at rt for 4 h. The solvent was evaporated and the residue was partitioned between 1N HCl (100 mL) and ether (150 mL). The aq. layer was extracted with ether (100 mL) and the combined ethereal layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was taken up in dioxane (15 mL) and 6N HCl (50 mL) was added. The mixture was heated to reflux for 90 min. The mixture was cooled to 0 C. and the volatiles were removed in vacuo. The solids were filtered off and washed with water. The solid was dried in vacuo to afford the title compound as a yellow solid (1.38 g, 56% yield). The title compound was only 70% pure. MS (ESI, m/z): 199.1 [M+H+] for C8H4N2OClF.

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. 127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2012/40989; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109306-86-7, 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.109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.

Example 20The boronic acid compound D was synthesized as described below. That is, 2-(2-bromophenyl)pyridine (J. Am. Chem. Soc., 2006, vol. 128, p. 6,790 and 6,791.) (4.0 mmol) was added in a flask of 50 mL filled with dry nitrogen together with toluene (6.4 mL) and tetrahydrofuran (1.6 mL) as a solvent and was cooled to -78 C. After a 1.5-M hexane solution of butyl lithium (3.1 mL, 4.8 mmol) was added to this solution dropwise, and the mixture was stirred at -78 C. for 30 minutes. To the reaction mixture was added triisopropyl borate (4.8 mL), and the mixture was stirred at room temperature for 19 hours. After the reaction mixture was concentrated under reduced pressure, the residue was purified by column chromatography (alumina, ethyl acetate-methanol=5:1), so that methyl ester of the boronic acid compound D was obtained. After this product was dissolved in a mixture of water and methanol, the solvent was removed at 50 C. to 60 C. under reduced pressure, so that the boronic acid compound D was obtained (669 mg, yield: 84%). The structure of the boronic acid compound D was identified by 1H NMR and 13C NMR. 1H NMR (CD3OD) delta 7.42 (dt, J=1.5, 7.5 Hz, 1H), 7.47 (dt, J=1.5, 7.5 Hz, 1H), 7.60 (ddd, J=0.9, 1.5, 7.5 Hz, 1H), 7.64 (ddd, J=1.5, 5.7, 7.5 Hz, 1H), 7.96 (ddd, J=1.2, 1.5, 7.5 Hz, 1H), 8.18 (ddd, J=1.2, 1.5, 8.1 Hz, 1H), 8.27 (ddd, J=1.5, 7.5, 8.1 Hz, 1H), 8.49 (ddd, J=0.9, 1.5, 5.7 Hz, 1H); 13C NMR (CD3OD) delta 119.3, 123.2, 125.0, 129.5, 131.7, 132.3, 138.9, 143.1, 144.7, 157.1.

The chemical industry reduces the impact on the environment during synthesis 109306-86-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY; US2011/319620; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem