Category: pyridine-derivatives

Reference of 6937-03-7, 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.6937-03-7, name is Methyl 2-aminoisonicotinate, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.

26 g of lithiumaluminum hydride was dissolved in 800 mL ofanhydrous THF. A solution of 103 g of methyl ether of2-aminoisonicotinate in 600 mL of anhydrous THFwas added at stirring and the formed slurry was boiledfor 3 h. After cooling water was carefully added, theprecipitate was filtered off and washed with 300 mL ofTHF. The combined filtrates were evaporated, theresidue was crystallized from benzene. Yield 61 g(73percent), mp 80?81.5°. 1H NMR spectrum (DMSO-d6),delta, ppm: 4.36 s (2), 5.19 s (1), 5.78 s (2), 6.40 d(1), 6.46 s (1), 7.81 d (1). 13 NMR spectrum(DMSO-d6), delta, ppm: 62.3, 105.2, 110.3, 147.7, 152.7,160.3. Found, percent: 57.63; 6.32; N 22.68. C6H8N2O.Calculated, percent: C 58.05; H 6.4; N 22.56.

Statistics shows that 6937-03-7 is playing an increasingly important role. we look forward to future research findings about Methyl 2-aminoisonicotinate.

Reference:
Short Survey; Lifshits; Ostapchuk; Brel; Russian Journal of Organic Chemistry; vol. 51; 5; (2015); p. 744 – 745; Zh. Org. Khim.; vol. 51; 5; (2015); p. 759 – 760,2;,
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.13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.Quality Control of 6-Bromopyridin-3-amine

Intermediate 51; 6-(2,6-Difluorophenyl)pyridin-3-amineIn a three neck round bottle flask, to a mixture of 1 ,3-difluorobenzene (23.24 mmol, 2.29 ml) in THF (30 ml) at -780C under argon atmosphere, a solution of n-BuLi (10.2 ml) in THF (2.5M) was added. The mixture was stirred at -78°C for 30 minutes and then it was heated to -5O0C. A solution of ZnCI2 (51 ml) in THF (0.5M) was added drop wise and the mixture was stirred at this temperature for 20 minutes. A solution of 6-bromopyridin-3-amine (11.56 mmol, 2.0 g) in THF (20 ml) and Pd(PPh3)4 (1.16 mmol, 1.3 g) were added respectively and the crude mixture was heated at 4O0C overnight. The solvent was evaporated and the crude mixture was purified by reverse phase chromatography eluting with a water-MeOH/AcN system affording 0.72 g (yield 30percent) of the expected product, delta 1H NMR (200 MHz, CDCI3): 3.83 (s, 2H), 6.95-7.00 (m, 2H), 7.06-7.09 (d, 1 H), 7.23- 7.32 (m, 2H)1 8.24 (s, 1 H). ESI/MS (m/e, percent): 207 [(M+1)\ 100].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-97-9, 6-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6271-78-9 ,Some common heterocyclic compound, 6271-78-9, molecular formula is C6H5ClN2O, 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 1-6 6-chloro-N-(7-chloro-2-(oxazol-2-yl)-4-oxo-1-phenyl-1,4-dihydroquinolin-3-ylmethyl)nicotin-amide A 5 mL round-bottomed flask was charged with 6-chloronicotinamide (14 mg, 0.091 mmol), sodium hydride (60% suspension in mineral oil, 5.0 mg, 0.013 mmol) and DMF (1 mL) to give a slightly white suspension. This mixture was stirred at 50 C for 15 min. During this time, the reaction mixture became more cloudy and difficult to stir. The reaction mixture was cooled to room temperature. A solution of 3-(bromomethyl)-7- chloro-2-(oxazol-2-yl)-l-phenylquinolin-4(lH)-one (38 mg, 0.091 mmol) in DMF (1 mL) was added dropwise to the room temperature reaction mixture. The reaction was stirred at 50 C over 1 hr. LC/MS at this time suggested formation of the desired product. The reaction mixture was allowed to cool gradually to room temperature, then it was stirred at room temperature overnight. The reaction was quenched via addition of 1 mL water slowly. The quenched reaction mixture was then partitioned between 20 mL ethyl acetate and 20 mL water. The organic phase was dried (MgS04), filtered, then concentrated over silica gel. The silica gel supported crude product was loaded onto a 40 gram silica gel column. Flash chromatography (75% ethyl acetate-hexanes ramped to 100% ethyl acetate) was used to partially purify the desired product 6-chloro-N-(7-chloro-2-(oxazol- 2-yl)-4-oxo- 1 -phenyl- 1 ,4-dihydroquinolin-3-ylmethyl)nicotinamide from the side product 6-chloro-N,N-bis((7-chloro-2-(oxazol-2-yl)-4-oxo-l -phenyl- l,4-dihydroquinolin-3- yl)methyl)nicotinamide. Homogeneous fractions were concentrated to provide 6-chloro- N-(7-chloro-2-(oxazol-2-yl)-4-oxo-l -phenyl- l,4-dihydroquinolin-3-ylmethyl)nicotin- amide as 1 mg (2% yield) of a white solid. 1H NMR (chloroform-d) delta ppm 8.75 (d, 7=2.4 Hz, 1 H) 8.42 (d, 7=8.6 Hz, 1 H) 7.99 (dd, 7=8.2, 2.7 Hz, 1 H) 7.68 (bs, 1 H), 7.58 (s, 1 H), 7.45 (m, 3 H), 7.39 (dd, 7=8.5, 2.0 Hz, 1 H) 7.34 (d, 7=8.2 Hz, 1 H) 7.28 (m, 2H) 7.13 (s, 1H) 6.85 (d, J=2.0 Hz, 1 H) 4.47 (d, 7=5.5 Hz, 2 H). MS calcd. for C25H16C12N4O3

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. 6271-78-9, 6-Chloropyridine-3-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BILOTTA, Joseph Anthony; CHEUNG, Adrian Wai-Hing; FIROOZNIA, Fariborz; GUERTIN, Kevin Richard; HAYDEN, Stuart; HAYNES, Nancy-Ellen; LUKACS-LESBURG, Christine M.; MARCOPULOS, Nicholas; MERTZ, Eric; QI, Lida; QIAN, Yimin; SO, Sung-Sau; TAN, Jenny; THAKKAR, Kshitij Chhabilbhai; WO2013/7676; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887583-90-6, 4-Bromo-2-(trifluoromethyl)pyridine, 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, COA of Formula: C6H3BrF3N, blongs to pyridine-derivatives compound. COA of Formula: C6H3BrF3N

A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 10.6 mL, 13.8 mmol) was added dropwise by syringe to a solution of 4-bromo-2-(trifluoromethyl)pyridine (3.12 g, 13.8 mmol) in dry THF (50 mL) at 0 C. After 30 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.38 g, 12.5 mmol) in THF (28.5 mL) was added to the Grignard solution by syringe at 0 C. The reaction mixture was warmed to room temperature over 2 hours after which it was quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate and washed with saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM) to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887583-90-6, 4-Bromo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1013648-04-8, Adding some certain compound to certain chemical reactions, such as: 1013648-04-8, name is Methyl 2,6-dichloro-4-methylnicotinate,molecular formula is C8H7Cl2NO2, 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 1013648-04-8.

) Synthesis of 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylesterA solution of 5.2 g (23.7 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester, 3.94 g (28.5 mmol) K2C03 and 2.06 ml (23.7 mmol) morpholine in DMF (48 ml) was heated to 60 C for 16 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1 ) provided 1.95 g (7.2 mmol, 30%) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

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. 1013648-04-8, Methyl 2,6-dichloro-4-methylnicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 407-20-5 ,Some common heterocyclic compound, 407-20-5, molecular formula is C5H3BrFN, 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 diisopropylamine (0.48 mL, 0.0034 mol) in dry tetrahydrofuran (10 mL) was added 1.6 M rc-butyl lithium in hexane (2.39 mL, 0.00369 mol) drop wise under nitrogen atmosphere at -78 C and stirred for 30 min at -78 C. To the above stirred mixture was added a solution of 3-bromo-5-fiuoropyridine (0.5 g, 0.00284 mol) in dry tetrahydrofuran at -78 C and stirred for 45 min. After 45 min, a solution of hexachloroethane in dry tetrahydrofuran was added to the above reaction mixture at -78 C and stirred for 30 min at -78 C. The reaction mixture was slowly warmed to RT and stirred for 1 h. The reaction was quenched with saturated solution of ammonium chloride (10 mL) and extracted with diethyl ether (25 mL x 3). The combined organic layer was washed with water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The obtained crude was purified with silica gel chromatography by hexane to afford the title compound. lH NMR (400 MHz,CDC13) delta: 8.58 (s, 1 H), 8.43 (s, 1 H). MS (M+l): 209.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,407-20-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
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. 934758-27-7, name is 2-Amino-6-bromopyridin-3-ol, the common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-6-bromopyridin-3-ol

A solution of 2-amino-6-bromopyridin-3-ol (500 mg, 2.29 mmol) in DMF (5 mL) was treated with potassium carbonate (367.5 mg, 2.66 mmol). 2-Bromo-2,2-difluoro- acetyl chloride (566 mg, 2.93 mmol) was added dropwise over 10 minutes with cooling in an ice-water bath. The reaction mixture was warmed to room temperature over 3 h, then heated at 50C for 18 h. The resulting mixture was concentrated under reduced pressure, then EtOAc (5 mL) and water (5 mL) were added. The organic layer was separated and washed with 2M aqueous HC1 (5 mL), saturated aqueous NaHC03 solution and brine, then dried (MgSC^). The crude material was concentrated under reduced pressure. (0855) Trituration of the resulting brown oil with DCM afforded the title compound (180 mg, 26%) as an orange solid. Method B HPLC-MS: MH+ mlz 264/266, RT 1.91 minutes (100%)

The synthetic route of 934758-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 39890-95-4 , The common heterocyclic compound, 39890-95-4, name is 2-Chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H3ClF3N, 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 2-chloro-6-(trifluoromethyl)pyridine (1.0 g, 5.5 mmol), piperazine (1.4 g, 16.0 mmol), and triethylamine (1.5 mL, 11.0 mmol) were mixed in DMF (10 mL) in a dealed tube. The mixture was heated at 100 C. overnight. The reaction mixture was concentrated and chromatographed on silica gel (ethyl acetate to EA/MeOH/Et3N=9:1:0.5) to give 1.05 g of the desired product. MS calculated for C10H12F3N3: (M+H) 232.1; found 232.1.

The synthetic route of 39890-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xue, Chu-Biao; Zheng, Changsheng; Feng, Hao; Xia, Michael; Glenn, Joseph; Cao, Ganfeng.; Metcalf, Brian W.; US2006/4018; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55314-16-4 , The common heterocyclic compound, 55314-16-4, name is 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one, molecular formula is C10H12N2O, 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.

3- [(Aminoiminomethyl)amino] -4-methyl-benzoic acid methylester mononitrate (10 g),3-(Dimethylamino)-1-(pyridine-3-yl)prop-2-en-1-one (7.3 g), sodium hydroxide (1.7 g) was added to 1-butanol (100 mL) in a round bottom flask under nitrogen atmosphere. The reaction mass was heated to reflux temperature and stirred for 12 his. Then the reaction mass was cooled to 25-35C and iN sodium hydroxide solution (1.5 g in 37 mLof DM wter) was added to it over a period of 20 mm. The reaction mass was heated to reflux temperature (120-125C) and then cooled to 25-35C. iN hydrochloric acid. (3.3 mL in 37 mL of DM water) was added to the reaction mass at 25-35C and stirred for an hour. The material formed was filtred, washed with DM water? and then dried under vacuum at 50-55C to provide the title compound (8.7 g).

The synthetic route of 55314-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; CHAVA, Satyanarayana; GORANTLA, Seeta Rama Anjaneyulu; INDUKURI, Venkata Sunil Kumar; MOTURU, Venkata Rama Krishna Murthy; JAMJANAM, Srivardhana Rao; SELA, Venkata Purushottama Siva Prasad; WO2015/87343; (2015); A2;,
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.1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate, molecular formula is C7H5BrFNO2, molecular weight is 234.02, as common compound, the synthetic route is as follows.Formula: C7H5BrFNO2

Intermediate 19-5 5-Fluoro-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxylic acid (1369) (1370) 500 mg of methyl 6-bromo-5-fluoropyridine-2-carboxylate were reacted analogously with 533 mg (1.2 equiv.) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole in the microwave at 120 C. for 90 min. This gave 380 mg (80% of theory) of the title compound as a crude product. (1371) UPLC-MS (Method A1): Rt=0.72 min (1372) MS (ESIpos): m/z=222 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1210419-26-3, Methyl 6-bromo-5-fluoropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BOTHE, Ulrich; SIEBENEICHER, Holger; SCHMIDT, Nicole; ROTGERI, Andrea; BOeMER, Ulf; RING, Sven; IRLBACHER, Horst; GUeNTHER, Judith; STEUBER, Holger; LANGE, Martin; SCHAeFER, Martina; (191 pag.)US2016/311833; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem