Tag: M.W:200-300

Synthetic Route of 7477-10-3, 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 7477-10-3 as follows.

To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicouenic acid in thionyl chloride (240 mi) are added 2 ml of DMF. This mixture is stirred at 60C until the evolution of gaz has ended. Then it is stirred at 80C for further 18 h. Residual thionyl chloride is removed under vacuo and the resulting residue is coevaporated three times with toluene. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50C to give 27.6 g (13.7 mmol/52 %) of the title compound as a light yellow solid with a melting point of 78C (dichloromethane/methanol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7477-10-3, its application will become more common.

Reference:
Patent; ALTANA PHARMA AG; WO2005/77947; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1156542-30-1 , The common heterocyclic compound, 1156542-30-1, name is 2-Bromo-5-fluoro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrF4N, 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.

To a 20 mL pressure vial was added (5 -2-amino-2,4-dimethylpentan-l-ol (323 mg, 2.462 mmol) and 2-bromo-5-fluoro-4-(trifluoromethyl)pyridine (601 mg, 2.462 mmol) in tetrahydrofuran (3.3 mL) to give a tan solution. Potassium tert- butoxide (2.95 mL, 2.95 mmol) (1.0 M in THF) was added dropwise under nitrogen. After 5 min stirring at rt, the vial was sealed and the mixture was stirred at 80 C for 18 h. The mixture was partitioned between water and EtO Ac. The layers were separated. The aqueous layer was extracted with EtO Ac. The combined organic solution was washed with brine, dried and concentrated to a tan oil. The crude was purified by silica gel chromatography up to 10% MeOH/CEhCh to afford (Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38923-08-9 , The common heterocyclic compound, 38923-08-9, name is Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate, molecular formula is C10H9N3O4, 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.

To a stirred solution of ethyl 6-nitroimidazo[l,2-a]pyridine-2-carboxylate (A34, 7.30 g, 31.73 mmol) in methanol(lOOmL) was added Pd/C(1.6 g, 15.86 mmol) under N2 atmosphere and the reaction mixture was stirred under H2 ballon pressure at room temperature for 4h. after completion of reaction mixture filtered through celite bed and washed with EtOAc. The filtrate was concentrated to dryness. The residue was washed with n-pentane dried to get compound ethyl 6-aminoimidazo[l,2-a]pyridine-2-carboxylate A35 as a green solid. Yield: 4.50 g(70%) LC-MS(ES) m/z : 205.99[M+H]+.

The synthetic route of 38923-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 178876-83-0, Methyl 6-amino-3-bromopicolinate, 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, 178876-83-0, blongs to pyridine-derivatives compound. SDS of cas: 178876-83-0

A solution of methyl 6-amino-3-bromopyridine-2-carboxylate (20.62 g) (T. R. Kelly and F. Lang, J Org. Chem. 61, 1996, 4623-4633) in chloroform (570 ml) was treated dropwise over 2 hours with bromine (4.62 ml) in chloroform (115 ml) and stirred 16 hours. The solution was washed with excess aqueous sodium bicarbonate, dried and evaporated. Crystallisation from EtOAc/hexane gave the bromopyridine (13.5 g). MS (APCI+) m/z 309,311, 313 (MH+, 70%), 295,297, 299 (100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,178876-83-0, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4282-47-7, 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 4282-47-7 as follows.

A solution of compound52(0.2 g, 1.03 mmol) in methanol (10 mL) was treated with 10% palladium on carbon (20 mg) and subjected to a hydrogen atmosphere. The mixture was stirred for a further 18 h and then filtered through a pad of Celite. The pad was washed with methanol (50 mL) and the combined filtrates evaporatedin vacuoto give the crude residue which was purified by flash chromatography on silica eluting withCH2Cl2-methanol-aqueous ammonia (95:4.5:0.5) to give amine53(0.15 g, 87%) as a brown solid; mp 89-92 C (lit mp 94-95 C); numax/cm-13333, 3210, 1606, 1586, 1519, 1294, 1181;deltaH(500 MHz, CDCl3) 8.62 (1 H, dt,J1.0, 5.0 Hz), 7.83 (2 H, d,J8.5 Hz), 7.68-7.61 (2 H, m), 7.11 (1 H, m) 6.75 (2 H, d,J8.5 Hz), 3.83 (2 H, br s);deltaC(125 MHz, CDCl3) 157.6, 149.5, 147.5, 136.6, 129.8, 128.1, 121.0, 119.4, 115.2;m/z(ESI) 171 ([M + H]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4282-47-7, its application will become more common.

Reference:
Article; Beinat, Corinne; Reekie, Tristan; Banister, Samuel D.; O’Brien-Brown, James; Xie, Teresa; Olson, Thao T.; Xiao, Yingxian; Harvey, Andrew; O’Connor, Susan; Coles, Carolyn; Grishin, Anton; Kolesik, Peter; Tsanaktsidis, John; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 277 – 301;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62150-46-3, 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. 62150-46-3, name is 4-Bromopicolinamide, molecular formula is C6H5BrN2O, 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 compound 53 (188 mg, 0.37 mmol), 4-bromopicolinamide (75 mg, 0.37 mmol) and 2 M aqueous Na2CO3 (0.6 mL, 1.20 mmol) in DME (3 mL) was degassed in vacuo for 15 min. To the mixture was added Pd(PPh3)4 (48 mg, 0.04 mmol) at room temperature. The mixture was stirred at 100 C under Ar for 8 h. The mixture was poured into water, and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluted with EtOAc in hexane), and crystallized from EtOAc/hexane to give the title compound (62 mg, 33%) as a white solid. mp: 220-222 C. 1H NMR (CDCl3) delta 1.14-1.29 (m, 2H), 1.59-1.76 (m, 2H), 2.20-2.30 (m, 4H), 2.94-3.05 (m, 1H), 3.61-3.75 (m, 1H), 4.60 (d, J = 7.2 Hz, 1H), 5.66 (br s, 1H), 6.34 (d, J = 8.7 Hz, 1H), 7.54 (dd, J = 8.7, 2.3 Hz, 1H), 7.65-7.75 (m, 1H), 7.86-7.94 (m, 3H), 7.99-8.06 (m, 2H), 8.29 (s, 1H), 8.48-8.50 (m, 1H), 8.71 (dd, J = 4.9, 0.8 Hz, 1H). LC/MS m/z 505.1 (M+H). Anal. Calcd for C24H23N4O3SF3: C, 57.13; H, 4.59; N, 11.10. Found: C, 57.04; H, 4.65; N, 10.92.

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 62150-46-3, 4-Bromopicolinamide.

Reference:
Article; Tawaraishi, Taisuke; Sakauchi, Nobuki; Hidaka, Kousuke; Yoshikawa, Kyoko; Okui, Toshitake; Kuno, Haruhiko; Chisaki, Ikumi; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3067 – 3072;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 947249-13-0, Adding some certain compound to certain chemical reactions, such as: 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine,molecular formula is C6H5BrF2N2O, 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 947249-13-0.

A glass reaction vessel (bomb) was charged with a mixture of 5-bromo-3- (difluoromethoxy)pyridin-2-amme(8, 6.212 g, 26,0 mmol), Bis(pinacolato)diboron (6.93 g, 27.3 mmol), Pd2(dba)3(0.952 g, 1.040 mraol), tricyclohexylphosph»ne(l .020 g, 3.64 mmol), and KOAc(5.36 g, 56.4 mmol) in anhydrous dioxane(70 ml). The mixture was carefully sparged with argon, the reaction vessel sealed, and heated to about 1 1OC in an oil bath for 24 hours. LCMS of aliquot indicated complete conversion of 8 to product I4H ([M+H]« 205.0 as acid, /R – 0.27min), Reaction mixture was diluted with EtOAc(70ml) aftere it cooled down to ambient temperature, filtered through neutral alumina(~30ml, 2.5ml thickness), alumina cake was washed throughly with IUtOAc(IOOmI), and filtrate was combined, concentrated and a light brown solid residue was obtained. The brown residue was triturated in heptane( 100ml) at (PC, desired product precipitated out, was collected via filtration and filter cake was rinsed throughly with heptane, final product 14H was obtained as a yellow solid(7.777g, 74% yield, }M+H]:…205.0, /kappa = 0.27min) after dried under high vacuum. ‘ H NMR confirmed structure, and an unidentified impurity at ~1.3ppm was found by 1H NMR. This impurity peak was probable a pinacole t-Bu group, and -1 : 1 tnol ratio to product. 1H NMR (400 MHz, CDCl,) delta ppm 8,27 (d, ./ « 1.5 Hz, 1 H), 7.55 (a, 1 H), 6.51 (t, JF-H= 73.6 Hz, 1H), 1.27 (8, 12 VI).

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. 947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; HUANG, Zilin; SENDZIK, Martin; WO2010/100127; (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.29681-42-3, name is Methyl 4-bromopicolinate, molecular formula is C7H6BrNO2, molecular weight is 216.032, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 4-bromopicolinate

Step 1: 2-hydroxymethyl-4-bromopyridine Methyl 4-bromo-pyridine formate (990mg, 4.58mmol) and ethanol (250mL) were added to a 250mL reaction flask. Under stirring, sodium borohydride (380mg, 10mg) was slowly added to the reaction system in batches. The reaction mixture was stirred for 18 hours under the protection of nitrogen at room temperature. After completion of the reaction, 5mL acetone was added to the reaction system, followed by stirring for 15 minutes. The reaction solution was filtered, concentrated and added with ethyl acetate and water, and the layers were separated. The organic phase was dried and concentrated to obtain the title compound (yellow liquid, 760mg, 88%), the crude product was used directly for the subsequent reaction. (MS: [M+1] 187.9)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29681-42-3, Methyl 4-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Pearl Biotechnology Limited Liability Company; DONG, Jiaqiang; ZHONG, Boyu; YUAN, Hongbin; SHI, Quan; CHU, Shaosong; ZHANG, Deyi; ZHANG, Ruihao; (219 pag.)EP3150592; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6268-43-5, 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.6268-43-5, name is 1,3-Di(pyridin-2-yl)urea, molecular formula is C11H10N4O, molecular weight is 214.22, as common compound, the synthetic route is as follows.

For R3 = NH-py and R1 = py in Example Scheme ES, the following example can be listed:? Using 10.0 mol% Zn(OAc)2.17H20, 1.0 equiv ACDG-NH-CO-NH-ACDG 5a, 52.0 equivisopropanol (ha), 140 C 24 h, a GO-yield of 59% of 2-aminopyridine (6a) was determinedwith TMB as an internal standard (calculated based on the formation of 2.0 equiv 2- aminopyridine (6a) = 100 % GO-yield).

The chemical industry reduces the impact on the environment during synthesis 6268-43-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; MAES, Bert; WYBON, Clarence; CHEN, Chen; BHEETER, Charles Beromeo; SERGUEEV, Serguei; (88 pag.)WO2017/46133; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 693286-31-6, Adding some certain compound to certain chemical reactions, such as: 693286-31-6, name is 4,6-Dichloro-2-methylnicotinic acid,molecular formula is C7H5Cl2NO2, 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 693286-31-6.

To a solution of 4, 6-dichloro-2-methyl-nicotinic acid (8. 5 g, 41.3 mmol) in anhydrous tetrahydrofuran (85 mL), 1,3-dicyclohexyl-carbodiimide (9.27 g, 44.9 mmol), 4- (DIMETHYLAMINO)-PYRIDINE (140 mg, 1.14 mmol), and cyclopentanol (5.1 mL, 4. 83 g, 56.2 mmol) are added in succession. The mixture is stirred for 15 minutes at room temperature and brought to reflux at which it is maintained for 1 hour. The reaction is cooled to ambient temperature and all volatiles are removed in vacuo. The residue is dissolved in a mixture of ethyl acetate and hexane (1: 12,200 mL) and the resultant suspension is filtered over a small pad of silica gel (45 g), which is subsequently rinsed with additional 200 mL of the same mixture of hexane and ethyl acetate. The obtained solution is concentrated in vacuo and the residue chromatographed on silica gel (hexane: ethyl acetate 15: 1) to afford 4, 6-dichloro-2- methyl-nicotinic acid cyclopentane ester as colorless oil.

According to the analysis of related databases, 693286-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/43925; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem