Pyridine-derivatives

Application of 126325-47-1 ,Some common heterocyclic compound, 126325-47-1, molecular formula is C6H7BrN2, 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.

Preparation VI; 6-Cyano-2-methyl-3-aminopyridine; A mixture of 3.5 g (18.6 mmol) of 6-bromo-2-methyl-3-aminopyridine, 352 mg (0.37 mmol) of tris(benzylideneacetone)dipalladium(0), 532 mg (0.92 mmol) of 1,1′-bis(diphenylphosphino)ferrocene, 146 mg (2.2 mmol) of zinc powder and 1.4 g (12 mmol) of zinc cyanide in 70 ml of N,N-dimethylacetamide is prepared and the reaction mixture is then stirred at 20 C. for 22 hours. It is diluted with 200 ml of ethyl acetate and washed with 2 N ammonium chloride solution. (Decantation is obtained only after filtration of the mixture on a filter aid of the Celite type.) The organic phase obtained is washed with sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (9/1; v/v) as the eluent to give 1.6 g of the expected compound in the form of a yellow powder (yield=65%). M.p.=192-196 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,126325-47-1, its application will become more common.

Reference:
Patent; Laboratoires Fournier S.A.; US2007/54955; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10128-91-3 ,Some common heterocyclic compound, 10128-91-3, molecular formula is C7H7NO3, 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.

General procedure: 2-Hydroxynicotinic acid methyl ester (CAS number 10128-91-3) (100-200 mg scale), the corresponding aryl iodide (0.95 equiv), CuBr (10 mol%), 2-ethylester cyclohexanone (20 mol%) and Cs2CO3 (2.2 equiv) were suspended in DMSO (anhydrous, 2-3 mL) in a sealed tube. The reaction was complete after about 18 h heating at 60 C. The mixture was diluted in EtOAc and washed with brine. The aqueous phase was re-extracted once with EtOAc. The combined organic phases were dried over anhydrous MgSO4, and the solids filtered off. The solvent was removed in vacuo and the resulting crude material purified by column chromatography over lica gel, EtOH/CH2Cl2. The products were isolated in good yields (53-58%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10128-91-3, its application will become more common.

Reference:
Article; Suarez, Rosa M.; Chevot, Franciane; Cavagnino, Andrea; Saettel, Nicolas; Radvanyi, Francois; Piguel, Sandrine; Bernard-Pierrot, Isabelle; Stoven, Veronique; Legraverend, Michel; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 2 – 25;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 15506-18-0, 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.15506-18-0, name is 1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C7H7NO3, molecular weight is 153.1354, as common compound, the synthetic route is as follows.

b) 3-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9- diazaspiro[5.5]undec-3-yl}carbonyl)-1-methylpyridin-2(lH)-oneN-methyl-2-hydroxynicotinic acid (45 mg, 0.29 mmol), Intermediate A (76 mg, 0.24 mmol), HATU (91.9 mg, 0.24 mmol) and triethylamine (43 mg, 0.43 mmol) in CH2Cl2 (4 mL) were mixed and stirred for Ih. The reaction mixture was diluted with saturated aqueous sodium carbonate (2 mL) and the product was extracted with dichloromethane and dried. The pure title compound was obtained by preparative HPLC.1H NMR (399.99 MHz, CD3OD) delta 7.81-7.71 (m, IH), 7.60-7.52 (m, IH), 7.32-7.26 (m, IH), 7.23-7.16 (m, IH), 6.97-6.88 (m, IH), 6.48-6.36 (m, IH), 4.32-4.19 (m, 2H), 3.79- 3.67 (m, 2H), 3.62-3.55 (m, 3H), 3.45-3.35 (m, 2H), 3.26-3.06 (m, 4H), 2.08-1.96 (m, 2H), 1.84-1.37 (m, 14H)APCI-MS m/z: 450.5 [MH+]HPLC (Method A) Retention time: 5.63 minHPLC (Method B) Retention time: 7.07 min

The chemical industry reduces the impact on the environment during synthesis 15506-18-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2007/30061; (2007); 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 86718-01-6, name is Methyl imidazo[1,2-a]pyridine-7-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Methyl imidazo[1,2-a]pyridine-7-carboxylate

Hydrazine monohydrate (10 ml, 636 mmol) was added to methyl imidazo[1,2-a]pyridine-7-carboxylate (CAS: 86718-01-6) (11.2 g, 63.57 mmol) in solution in MeOH (300 ml). The reaction mixture was refluxed for 3 hours, then additional hydrazine monohydrate (10 ml, 636 mmol) was added and the mixture was refluxed overnight. After cooling to room temperature, the precipitate was filtered, washed with EtOH and dried yielding 13 g (quantitative) of intermediate shown.

With the rapid development of chemical substances, we look forward to future research findings about 86718-01-6.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2012/41000; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 127406-56-8, 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 127406-56-8 as follows.

EXAMPLE 5; Synthesis of 3-hydroxy-4-(pyridine-2-yl)benzaldehyde (5a)In a 20 mL tube, 4-(pyridine-2-yl)benzaldehyde (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H2O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under oxygen. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 1300C for 36 h. The reaction mixture was diluted with 20 mL Of CH2Cl2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. After purification by column chromatography on silica gel with a gradient eluent of hexane and ether (Rf = 0.29 in 2:1 hexane: ether), the title product was obtained as a pale yellow solid (25.7 mg, 43%). 1H NMR (400 MHz, CDCl3) delta 14.59 (s, IH), 10.00 (s, IH), 8.58 (d, J = 4.8 Hz, IH), 8.02-7.92 (m, 3H), 7.50 (s, IH), 7.44 (d, J= 8.4 Hz, IH), 7.36 (t, J= 7.2 Hz, IH); 13C NMR (100 MHz, CDCl3) delta 191.93, 160.41, 156.55, 146.09, 138.34, 138.15, 126.74, 123.73, 122.75, 120.49, 120.01, 118.71; IR (thin film) v 3055, 1698, 1594, 1419, 1265 cm”1; HRMS (TOF) Calcd for C12Hi0NO2 (M + H) 200.0712, found 200.0708.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,127406-56-8, its application will become more common.

Reference:
Patent; BRANDEIS UNIVERSITY; WO2007/123910; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 885277-08-7, Adding some certain compound to certain chemical reactions, such as: 885277-08-7, name is 5-Chloropyridine-2-sulfonyl chloride,molecular formula is C5H3Cl2NO2S, 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 885277-08-7.

To a solution of Example 3B (60.0 mg, 0.187 mmol) and 5-chloropyridine-2-sulfonyl chloride (43.6 mg, 0.205 mmol) in N,N-dimethylformamide (1.5 mL) was added triethylamine (0.065 mL, 0.467 mmol). The mixture was stirred for 2 hours, quenched with saturated NaHC( and brine, and extracted with ethyl acetate (2x). The combined organic layers were concentrated, and the residue was purified by reverse-phase HPLC (see protocol in Example 273E) to provide the title compound (26.7 mg, 31 %). JH NMR (500 MHz, DMSO-<) delta ppm 9.05 (s, 1H), 8.85 (dd, J = 2.5, 0.7 Hz, 1H), 8.65 (s, 1H), 8.24 (dd, J = 8.4, 2.4 Hz, 1H), 8.00 (dd, J = 8.4, 0.7 Hz, 1H), 7.48 (t, J = 8.8 Hz, 1H), 7.03 (dd, J = 11.3, 2.9 Hz, 1H), 6.81 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.42 (s, 2H), 1.96 (s, 6H); MS (ESI+) m/z 460.3 (M+H)+. 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. 885277-08-7, 5-Chloropyridine-2-sulfonyl chloride, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); 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. 1702-17-6, name is 3,6-Dichloropicolinic acid, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3Cl2NO2

Under a nitrogen atmosphere, (Purity: 95.1 wt%) of 3,6-dichloropyridine-2-carboxylic acid, 63 g of toluene and 0.48 g of N, N-dimethylformamide was added dropwise at 80 C over 0.5 hour And 17.04 g of thionyl chloride was added thereto, followed by stirring at the same temperature for 1.5 hours. The reaction mixture was cooled to 50 C and concentrated under reduced pressure to give 47.67 g of a toluene solution of 3,6-dichloropyridine-2-carboxy chloride (confirmed by mixing the reaction mixture with methanol).

The synthetic route of 1702-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; KIMURA, TAKAHIRO; MAEHATA, RYOTA; (41 pag.)TW2016/5803; (2016); A;,
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.15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, molecular weight is 281.89, as common compound, the synthetic route is as follows.SDS of cas: 15862-37-0

To a stirred solution of 2,5-dibromo-3-nitropyridine (226 mg, 0.802 mmol), (4- (1 ,4-dimethyl- 1H- 1 ,2,3-triazol-5-yl)-3-fluorophenyl)boronic acid (282.6 mg, 1.20 mmol),and PdC12(dppf) (29.3 mg, 0.040 mmol) in THF (8.0 mL) was added tripotassium phosphate (3M in H20, 802 pi, 2.41 mmol), purged with N2 (vacuum/N2 x3) and the reaction was heated at 75 C with stirring for 1 h. The reaction was cooled to room temperature and concentrated. The residue was suspended in EtOAc, filtered throughCelite, washed with EtOAc, concentrated. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0% to 100% using solvent A/B=CH2C12/EtOAc over 15 column volumes, RediSep Si02 40 g, loaded as DCM solution). Obtained the product (190 mg, 61%): HPLC: RT=0.91 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.1%TFA, 1.5 mm gradient,wavelength=254nm); MS (ES): m/z=392 [M+1f

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-37-0, 2,5-Dibromo-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUESNELLE, Claude A.; HARIKRISHNAN, Lalgudi S.; HILL, Matthew D.; (180 pag.)WO2016/183114; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 31301-51-6, Adding some certain compound to certain chemical reactions, such as: 31301-51-6, name is 2-Chloro-5-fluoropyridine,molecular formula is C5H3ClFN, 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 31301-51-6.

1st step A tetrahydrofuran (5 ml) solution containing 2-chloro-5-fluoropyridine (500 mg) was added to a tetrahydrofuran (20 ml) solution containing lithium-N,N-diisopropylamide (2M tetrahydrofuran/ethylbenzene/heptane solution) (2.9 ml) at -75C in a nitrogen atmosphere, followed by stirring at -75C for 3 hours. Subsequently, a tetrahydrofuran (5 ml) solution containing iodine (1.16 g) was added, followed by stirring at -75C for 1 hour. Then, water/tetrahydrofuran (2 ml/8 ml), water (10 ml), and 3M aqueous sodium thiosulfate were slowly added at -75C, -50C, and -35C, respectively, to the reaction solution. The reaction solution was adjusted to room temperature, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane : ethyl acetate = 20:1 to 10:1), and a white solid of 2-chloro-5-fluoro-4-iodopyridine (457 mg) was thus obtained. 1H-NMR (CDCl3, 300MHz) delta:8.14 (s, 1H), 7.77 (d, 1H, J = 4.3Hz) 2nd step

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. 31301-51-6, 2-Chloro-5-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJIFILM Corporation; FUJIWARA, Hideyasu; SATO, Kimihiko; MIZUMOTO, Shinsuke; SATO, Yuichiro; KURIHARA, Hideki; KUBO, Yohei; NAKATA, Hiyoku; BABA, Yasutaka; TAMURA, Takashi; KUNIYOSHI, Hidenobu; HAGIWARA, Shinji; YAMAMOTO, Mari; (630 pag.)EP2589592; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 84249-14-9, name is 2-Amino-4-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H5BrN2

Step 1: N-(4-bromopyridin-2-yl)acetamide To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol). The reaction mixture was allowed to stir at 140 C. for 3 h and then allowed to cool to rt. Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH. The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89%) as a white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 84249-14-9, 2-Amino-4-bromopyridine.

Reference:
Patent; MILLENNIUM PHARMACEUTICALLS, INC.; BHARATHAN, INDU T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CILLIS, Courtney A.; D’AMORE, Natalie; FLE,OMG, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Kirsta E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen g.; VOS, Tricia J.; XU, He; YE, Yingchun; (48 pag.)US2016/333007; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem