Category: pyridine-derivatives

Application of 1121056-94-7, 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. 1121056-94-7, name is 5-Nitro-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4F3N3O2, 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 stirred solution of 5-nitro-3-(trifluoromethyl)pyridin-2-amine (2 g, 9.66 mmol) in dichloromethane (20 mL) was added DMAP (1.29 g, 10.62 mmol), Et3N (2.69 mL, 19.31 mmol) and acetyl chloride (0.758 mL, 10.62 mmol) at room temperature and the resulting reaction mixture was stirred for 1H. After completion of the reaction, reaction mixture was neutralized with aqueous (1 M) solution of potassium carbonate. Aqueous phase was extracted with ethyl acetate (20 mL x 3), combined organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was rotary evaporated and residue was purified by flash column chromatography (silica gel) to afford 1.1 g (46%) of the titled product as yellow solid. 1HNMR (400 MHz, DMSO-d6) U10.73 (s, 1H), 9.47 (d, J = 2.6 Hz, 1H), 8.84 (d, J = 2.6 Hz, 1H), 2.14 (s, 3H); ESI-MS (m/z) 249.80 (MH)

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 1121056-94-7, 5-Nitro-3-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; LUPIN LIMITED; KUKREJA, Gagan; IRLAPATI, Nageswara, Rao; JAGDALE, Arun, Rangnath; DESHMUKH, Gokul, Keruji; VYAVAHARE, Vinod, Popatrao; KULKARNI, Kiran, Chandrashekhar; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (366 pag.)WO2018/20474; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1005785-85-2, 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. 1005785-85-2, name is 5-(tert-Butyl)picolinic acid, molecular formula is C10H13NO2, 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 solution of carboxylic acid (80 mg, 0.45 mmol) and CDI (145 mg, 0.90 mmol) in DMF (4 mL) was stirred at rt for 0.5 h, followed by the addition of the amine (110 mg, 0.45 mmol) and Et3N (137 mg, 1.35 mmol) and the mixture was stirred at rt for 16 h. After diluted with water (5 mL), the mixture was extracted with EtOAc (5 mL x 2). The combined organics were concentrated in vacuo and the residue was purified by reverse phase chromatography (MeOH/H2O with 0.05% NH3.H2O as mobile phase) to afford the title compound (26 mg, yield 15%) as a yellow solid. ESI-MS (M+H)+: 400.2.1H NMR (400 MHz, CD3OD) : 8.77-8.74 (m, 2H), 8.06-8.03 (m, 2H), 7.92-7.95 (m, 2H), 7.54-7.51 (m, 2H), 6.86 (d, J = 4.0 Hz, 1H), 4.74 (s, 2H), 2.53 (s, 3H), 1.42 (s, 9H).

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 1005785-85-2, 5-(tert-Butyl)picolinic acid.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52334-51-7, 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.52334-51-7, name is 3-Amino-5-methylpyridin-2(1H)-one, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

(Reference Example 5-2) At room temperature, to a mixed solvent solution of 3-amino-5-methylpyridin-2-ol (4.03 g) in tetrahydrofuran (50 ml) and 1,2-dichloroethane (50 ml) were added tert-butyl 4-oxopiperidine–1-carboxylate (13.04 g), sodium triacetoxyborohydride (13.87 g) and acetic acid (3.75 ml), followed by heating at reflux for 16 hours. After the temperature was brought back to room temperature, 1 N aqueous sodium hydroxide solution was added, and extracted with chloroform. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford tert-butyl 4-[(2-hydroxy-5-methylpyridin-3-yl)amino]piperidine-1-carboxylate (7.6 g). 1H NMR (400 MHz, CDCl3) delta 1.40-1.50 (m, 2H), 1.47 (s, 9H), 1.98-2.10 (m, 2H), 2.06 (s, 3H), 2.92-3.02 (m, 2H), 3.32-3.41 (m, 1H), 3.95-4.10 (m, 2H), 4.78-4.83 (m, 1H), 6.16 (s, 1H), 6.48 (s, 1H), 11.5-11.8 (br m, 1H).

The chemical industry reduces the impact on the environment during synthesis 52334-51-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 49669-13-8, 2-Acetyl-6-bromopyridine, 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, Formula: C7H6BrNO, blongs to pyridine-derivatives compound. Formula: C7H6BrNO

A solution of l-(6~bromorhoyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 ml) at 00C was treated with methyl magnesium bromide (8.33 ml, 25.0 mmol). After 3 hours, water was added to quench excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound. LRMS (APCI) calc’d for C8H1 jBrNO [M+H]+: 216, Found: 216.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49669-13-8, 2-Acetyl-6-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; MACHACEK, Michelle, R.; HAIDLE, Andrew; ZABIEREK, Anna, A.; KONRAD, Kaleen, M.; ALTMAN, Michael, D.; WO2010/11375; (2010); A2;,
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. 59105-50-9, name is (5-Bromopyridin-3-yl)(phenyl)methanone, the common compound, a new synthetic route is introduced below. COA of Formula: C12H8BrNO

General procedure: Pd(PPh3)4 (17.3 mg, 0.015 mmol) was added to a solution of 3-benzoy-5-bromo pyridine(130.1 mg, 0.5 mmol) and aryl boronic acid (0.6 mmol) in MeOH (0.2 mL), toluene (0.8 mL),and 2 M Na2CO3 (0.2mL) under N2. The mixture was heated to 75 C for 2 h, and then cooledto room temperature and concentrated under reduced pressure. Water was added to theresidue and the aq. phase was extracted with DCM (3 × 5 mL). The combined organic layerswere washed with brine, dried over Na2SO4, and evaporated to obtain the crude product.Purification by column chromatography on silica gel afforded the desired product.

The synthetic route of 59105-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Yun; Sun, Jian; Molecules; vol. 24; 3; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 777931-67-6 , The common heterocyclic compound, 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine, molecular formula is C6H5BrClNO, 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 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.

The synthetic route of 777931-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 119396-04-2, 4-Chloro-2-(chloromethyl)pyridine hydrochloride, 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, 119396-04-2, blongs to pyridine-derivatives compound. Computed Properties of C6H6Cl3N

4-chloro-2-(chloromethyl)pyridine hydrochloride (200 mg, 1.02 mmol) was dissolved in chloroform (15 mL) and cooled in water/ice bath m-chloroperoxobenzoic acid (77%, 350mg, 1.56 mmol) was added and the reaction mixture was stirred for 24 hours while letting towarm up to room temperature. The solvent was evaporated on rotary evaporator and theresidue was purified by flash chromatography on silica in 5% methanol / 95 %dichloromethane mixture, giving 143 mg of the product as white solid (0.803 mmol, 79 % yield).500 MHz): 4.90 (C H2, s, 2H); 7.26 ( arom ., dd, 1H,3/HH= 7 Hz,4/HH = 3 Hz); 7.64 (arom., d, 1H,4/HH= 3 Hz); 8.20 (arom., d, 1H,3/HH= 7 Hz);13C{ NMR (CDCl3, 25 C, 125 MHz): 5c 39.6 (CH2, s); 125.6 (arom., s); 125.9 (arom., s); 132.4 (arom., s); 140.2 (arom., s); 148.7 (arom., s).HRMS (ESI) m/z: [(M + H)+] (C6H6Cl2NO) calculated: 177.9821, found: 177.9820.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,119396-04-2, its application will become more common.

Reference:
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; POLASEK, Miloslav; (102 pag.)WO2019/106182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2739-74-4, 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. 2739-74-4, name is Ethyl 3-(2-Pyridyl)propanoate, molecular formula is C10H13NO2, 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 3-(2-pyridyl)propanoic acid, hydrazide (5) STR16 To a stirring 5 mL EtOH solution of 0.58 g (3.2 mmol) of ethyl 3-(2-pyridinyl)propanoate (4), prepared as described above in Example 4, was added 0.32 g (6.5 mmol) of hydrazine hydrate. The reaction was heated at reflux for three weeks. Although the reaction was still incomplete, the solvent was removed under vacuum. The resulting gum was triturated with diethyl ether (Et2 O). The product remained a gum. The yield of 3-(2-pyridyl)propanoic acid, hydrazide (5) was 0.22 g (42%). This product was used immediately in the manner described in Example 6 below.

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 2739-74-4, Ethyl 3-(2-Pyridyl)propanoate.

Reference:
Patent; G. D. Searle & Co.; US5378840; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16328-62-4, 1H-Imidazo[4,5-b]pyridin-2(3H)-one, 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, Quality Control of 1H-Imidazo[4,5-b]pyridin-2(3H)-one, blongs to pyridine-derivatives compound. Quality Control of 1H-Imidazo[4,5-b]pyridin-2(3H)-one

Under argon, 1 ,3-dihydroimidazo[4,5-b]pyridin-2-one (1.500 g, 1 1.10 mmol) was dissolved in DMF (20 ml_). Then sodium hydride (0.4662 g, 1 1 .66 mmol) was added portion-wise over 15 minutes. The resulting suspension was stirred at room temperature for 1 hour. Then di-tert-butyl dicarbonate (2.47 g, 1 1.10 mmol), dissolved into DMF (16.9 ml_), was added dropwise over 10 minutes and the orange solution obtained was stirred at room temperature for 3 hours. Some MeOH was carefully added to quench the reaction mixture and then water was added. The pH of the solution was 8 to 9. The aqueous layer was extracted once with ethyl acetate and this extract was discarded (removal of impurities) then the pH was adjusted to 7 with 4 M aq. HCI solution and extraction was carried out with ethyl acetate. The combined organic layers were washed with water (x2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure at 40C to afford tert-butyl 2-oxo-3H- im idazo[4 , 5-b] pyrid ine- 1 -carboxylate. NMR (400 MHz, CDCI3): d ppm 8.80-10.50 (br s, 1 H), 8.13 (m, 1 H), 8.00 (dd, J=7.89, 1.28 Hz, 1 H), 7.10 (dd, J=7.89, 5.32 Hz, 1 H), 1.69 (s, 9H). LC-MS: Rt = 0.75 min, MS ES+ = 236 (M+H+).

The synthetic route of 16328-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA CROP PROTECTION AG; BIGOT, Aurelien; SCHAETZER, Juergen, Harry; JUNG, Pierre, Joseph, Marcel; STOLLER, Andre; GAGNEPAIN, Julien, Daniel, Henri; HALL, Roger, Graham; RENDINE, Stefano; COMPAGNONE, Nicola; (122 pag.)WO2020/30503; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

Step B: 3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamine 2-(2-Chloro-4-nitro-phenoxymethyl)-pyridine (2.4 g, 9.07 mmol) is suspended in MeOH (30 ml) and treated wet 5% Pt/C (Degussa type, Aldrich, 0.8 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture is stirred under hydrogen atmosphere until reaction is complete by TLC (ca 2 hours). The reaction mixture is filtered through a Celite plug and the solvent is removed under reduced pressure. The crude product is redissolved in DCM, dried (MgSO4) and concentrated to yield 1.7 g (7.23 mmol, 80%) of the desired product.

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. 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wallace, Eli; Topolov, George; Zhao, Qian; Lyssikatos, Joseph P.; US2005/101617; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem