Category: pyridine-derivatives

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.36052-27-4, name is Methyl 3-aminopicolinate, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.Product Details of 36052-27-4

Step 2;. Preparation of 3-amino-6-bromo-pyridine-2-carboxylic acid methyl ester; Add a solution of 2 M sulfuric acid (2 mL) to a suspension of 3-amino-pyridine-2- carboxylic acid methyl ester (0.59 g, 3.88 mmol) in water (10 mL) and stir the mixture until the precipitate is dissolved. Add dropwise a solution of bromine (0.199 mL, 3.88 mmol) in acetic acid (1.5 mL). Add a solution of 2 M sodium hydroxide until pH = 6 and extract with ethyl acetate. Separate the organic layer and extract with ethyl acetate. Dry the combined organic layers over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue using silica gel chromatography eluting with ethyl acetate/hexanes to afford the title compound (0.616 g, 69%). H-NMR (CDCl3,300 MHz) : No. 3.90 (s, 3 H) ; 6.90 (d, J = 8.5 Hz, 1H), 7.30 (d, J= 8.5 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36052-27-4, Methyl 3-aminopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/97805; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 146679-66-5, 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.146679-66-5, name is 3-Bromo-4-pyridinemethanol, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

To a solution of 3bromo-4-(hydroxymethyl)pyridine 4 (1.593 g, 8.47 mmol) in dichioromethane (20 mL) was added imidazole (0.692 g, 10.17 mmol) and tert-butyldimethylsilyl chloride (1.534 g, 10.17 mmol) at 0C and the reaction mixture was stirred for 18 h at ft. The solution was extractedwith DCM and the organic phase was washed with brine, dried and concentrated under vacuum. Purification by silica gel column chromatography using EtOAc/DCM (1/9) as eluent gave j (2.518 g, 98 %).?H NMR (CDC13, 300 MHz, 298 K, 6 ppm): 8.60 (s, 1 H), 8.52 (d, IH, J 4.8 Hz), 7.52 (d, 1H, J= 4.8 Hz), 4.71 (s, 2 H), 0.97 (s, 9 H), 0.15 (s, 6H).13C NMR (CDC13, 75.5 MHz, 298K, 8 ppm): 150.90, 149.67, 148.54, 122.19, 119.20, 63.78, 25.96,18,43, 5.31.GC/MS (m/z): [M-t-Butyl] 244. IR (KBr, v, cm?): 3046, 2953, 2887, 2857, 2709, 1926, 1789, 1737, 1587, 1472, 1445, 1397, 1373, 1360, 1261, 1172, 1114, 1079, 839, 778, 706, 673.

The chemical industry reduces the impact on the environment during synthesis 146679-66-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INSA (INSTITUT NATIONAL DES SCIENCES APPLIQUEES) DE ROUEN; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); UNIVERSITE DE ROUEN; VFP THERAPIES; MARSAIS, Francis; LEVACHER, Vincent; PAPAMICAEL, Cyril; BOHN, Pierre; PEAUGER, Ludovic; GEMBUS, Vincent; LE FUR, Nicolas; DUMARTIN-LEPINE, Marie-Laurence; WO2014/114742; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 119285-07-3, Adding some certain compound to certain chemical reactions, such as: 119285-07-3, name is tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate,molecular formula is C14H22N4O2, 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 119285-07-3.

To a solution of 2- (PIPERAZINE-N-T-BUTOXYCARBONYL)-5-AMINO pyridine (70 g, 0.251798 moles) dissolved in acetone (700 ml), sodium bicarbonate (42.3 g, 0.503597 moles) dissolved in water (350 ml), was added and cooled to 0 oC. BENZYLCHLOROFORMATE (85.8 g, 0.503597 moles) was added to the reaction mixture at 0 oC dropwise. After complete addition, the reaction mixture was kept at room temperature for 12 hours. Acetone was removed from the reaction mixture and diluted further with ethylacetate (2L). Washed the ethylacetate layer with water and brine solution. Dried over anhydrous sodium sulphate and concentrated to dryness. The crude compound was crystallized using ethylacetate and hexane to yield the title compound (67.4 g, yield 65 %).

According to the analysis of related databases, 119285-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORCHID CHEMICALS AND PHARMACEUTICALS LTD.; WO2005/3087; (2005); 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.58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Formula: C8H7Cl2NO2

3-[(2,2-Difluoro-1-methyl-cyclopropyl)methoxy]-1H-pyrazole (490 mg, 2.604 mmol) was dissolved in DMF (5 mL). Ethyl 2,6-dichloropyridine-3-carboxylate (approximately 573.0 mg, 2.604 mmol) was added followed by 1,4-diazabicyclo[2.2.2]octane(approximately 58.42 mg, 0.5208 mmol) and finely ground potassium carbonate (approximately 539.8 mg, 3.906 mmol). The reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2× 50 mL). The combined organic layers were then washed with brine (1× 75 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was isolated by silica gel column chromatography eluting with a 0-20% EtOAc/hexane gradient on a 40 gram silica gel column. Ethyl 2- chloro-6-[3-[(2,2-difluoro-1-methyl-cyclopropyl)methoxy]pyrazol-1-yl]pyridine-3- carboxylate (797 mg, 82%) was obtained as a white solid.1H NMR (400 MHz, DMSO- d6) delta 8.46 (dd, J = 2.8, 0.9 Hz, 1H), 8.41 (dd, J = 8.4, 0.9 Hz, 1H), 7.75 (dd, J = 8.5, 0.9 Hz, 1H), 6.27 (dd, J = 2.9, 0.9 Hz, 1H), 4.44 – 4.37 (m, 1H), 4.37 – 4.31 (m, 2H), 4.17 (d, J = 10.8 Hz, 1H), 1.67 (q, J = 8.9 Hz, 1H), 1.42 (q, J = 8.4 Hz, 1H), 1.38 – 1.30 (m, 6H). ESI-MS m/z calc.371.08484, found 372.0 (M+1)+; Retention time: 2.09 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-86-4, Ethyl 2,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ABELA, Alexander, Russell; ALCACIO, Timothy; ANDERSON, Corey; ANGELL, Paul, Timothy; BAEK, Minson; CLEMENS, Jeremy, J.; CLEVELAND, Thomas; FERRIS, Lori, Ann; GROOTENHUIS, Peter Diederik, Jan; GROSS, Raymond, Stanley; GULEVICH, Anton; HADIDA RUAH, Sara, Sabina; HSIA, Clara, Kuang-Ju; HUGHES, Robert, M.; JOSHI, Pramod, Virupax; KANG, Ping; KESHAVARZ-SHOKRI, Ali; KHATUYA, Haripada; KRENITSKY, Paul, John; MCCARTNEY, Jason; MILLER, Mark, Thomas; PARASELLI, Prasuna; PIERRE, Fabrice Jean, Denis; SHI, Yi; SHRESTHA, Muna; SIESEL, David, Andrew; STAVROPOULOS, Kathy; TERMIN, Andreas, P.; UY, Johnny; VAN GOOR, Fredrick, F.; YOUNG, Tomothy, John; ZHOU, Jinglan; (398 pag.)WO2018/107100; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885266-91-1, 1-(2-Aminopyridin-4-yl)ethanol, 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, Recommanded Product: 885266-91-1, blongs to pyridine-derivatives compound. Recommanded Product: 885266-91-1

To a solution of 8-(tert-butylamino)-6-chloro-2-(2-hydroxyethyl)-2,7-naphthyridin- l(2H)-one (29.6 mg, 0.10 mmol) in 1,4-dioxane (1 mL) were added crude l-(2-aminopyridin-4-yl)ethanol (estimate 0.20 mmol), Cs2CO3 (130.3 mg, 0.40 mmol), and a catalytic amount of Pd(dba)3 and Xantphos. The reaction mixture was purged with N2 and heated at 100 C overnight. The mixture was then cooled, quenched with H2O and extracted with EtOAc. The combined organic layer was concentrated and purified by preparatory LC/MS to provide title compound; 1H NMR (CD3OD, 400 MHz) delta 8.16 (d, /= 5.6 Hz, 1H), 7.69 (s, 1H), 7.23 (d, / = 7.6 Hz, 1H), 6.97 (d, /= 5.6 Hz, 1H), 6.59 (s, 1H), 6.24 (d, / = 7.6 Hz, 1H), 4.81 (q, / = 6.4 Hz, 1H), 3.99 (t, /= 5.2 Hz, 2H), 3.81 (t, /= 5.2 Hz, 2H), 1.57 (s, 9H), 1.45 (d, / = 6.4 Hz, 3H); ESI-MS ml z 398.2 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885266-91-1, 1-(2-Aminopyridin-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; CHE, Jianwei; CHEN, Bei; DING, Qiang; HAO, Xueshi; HE, Xiaohui; JIANG, Songchun; JIN, Qihui; JIN, Yunho; LIU, Hong; LIU, Yahua; OKRAM, Barun; UNO, Tetsuo; WU, Xu; YANG, Kunyong; ZHU, Xuefeng; WO2011/14515; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68325-15-5 , The common heterocyclic compound, 68325-15-5, name is 3-Chloro-4-cyanopyridine, molecular formula is C6H3ClN2, 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.

Reference Production Example 80To a mixture of 1.39 g of 3-chloro-isonicotinonitrile, 1.10 g of 2,2,2- trifluoroethanol and 5 mL of DMF, 0.40 g of 60% sodium hydride (oily) was added under ice cooling, followed by stirring for 20 minutes, heating to room temperature and further stirring for 7.5 hours. After ice cooling again, 0.20 g of 60% sodium hydride (oily) was added, followed by heating to room temperature and further stirring for 15 hours. Under ice cooling, water was added and the precipitated crystal was washed with water, collected by filtration and then dried under reduced pressure to obtain 1.63 g of 3-(2,2,2-trifluoroethoxy)- isonicotinonitrile. H-NMR (CDC13 ) delta : 8.53-8.52(br m, 1H), 8.51(d, J=4.9Hz, 1H), 7.53(dd, J=4.9, 0.6Hz,1H), 4.62(q, J=7.7Hz, 2H)

The synthetic route of 68325-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49222; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5470-17-7, 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 5470-17-7 as follows.

In a 250 mL round bottom flask, 3-bromo-2-chloro-5-nitropyridine (3 g, 12.63 mmol), ammonium chloride (1.35 g, 25.2 mmol) and zinc dust (8.79 g, 134 mmol) were suspended in MeOH (50 ml). The reaction mixture was heated for 2 hrs at 90 C. The reaction was cooled to room temperature, filtered over celite, and concentrated in vacuo. The resulting solid was adsorbed onto silica and purified by silica gel chromatography (25-55% EtO Ac/Heptane). The title compound (1.85 g, 8.92 mmol, 70.6 % yield) was obtained as a yellow solid. LCMS (m/z): 219.1 (MH+); retention time = 0.77 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-17-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William, R.; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; MARTIN, Eric, J.; PAN, Yue; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66070; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5912-18-5 , The common heterocyclic compound, 5912-18-5, name is 4,6-Dichloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4Cl2N2, 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.

4,6-dichloro-1H-pyrrolo[2,3-b]pyridine (1.0 eq) was dissolved in DMF and the temperature was lowered to minus 10 C.To the mixture was added N-iodosuccinimide (1.1 equivalent), the temperature was raised to room temperature, and stirred for 1 hour. After the reaction, ice water was added to induce precipitation. The formed precipitate was filtered to give the desired compound as white. (Yield: 100%).

The synthetic route of 5912-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dae Caliber Buk Peak Medical Industry Promotion Foundation; Korea Research Institute of Bioscience and Biotechnology; Daegu Gyeongbuk Institute of Science & Technology; Choi Hwan-geun; Go Eun-hwa; Cho Jung-hui; Son Jeong-beom; Go I-gyeong; Park Jin-hui; Kim So-yeong; Kang Seok-yong; Lee Seung-yeon; Ryu Hui-yun; Kim Nam-du; Kim Sang-beom; Lee Seon-hwa; Kim Da-ye; Lee Seon-ju; Cho Seong-chan; Lee Gyu-seon; Ryu Gwon; Choi Mi-ri; Gu Ja-uk; Huh Hyang-suk; (84 pag.)KR101896568; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-13-2, 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.74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.

To a solution of 5-bromopyridin-3-ol (LI) (174 mg, 1.0 mmol) in DMF (3 mL) was added potassium carbonate (415 mg, 3.0 mmol). The slurry was heated at 90C for 1 hour and then cooled to 25C. The (bromomethyl)benzene (LV) (171 mg, 1.0 mmol) was added and the mixture was stirred at 25C overnight. The reaction was worked-up using a saturated sodium bicarbonate and ethyl acetate extraction. The product was purified by ISCO column eluted with 40- 100% EtOAc-Hexanes. The 3-(benzyloxy)-5-bromopyridine (LVI) (105 mg, 0.398 mmol, 39.8 % yield) was obtained as yellow oil.. MS: 266.1. ESIMS found for C12H10BrNO m/z 266.1 (M+H).

Statistics shows that 74115-13-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-pyridinol.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (322 pag.)WO2016/40193; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 78686-83-6, 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 78686-83-6, name is Methyl 2-chloro-5-iodonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 5-(3-Chloro-5-methvIphenyl)-2-(l -methyl- 1H-pyrazol-4-vQ nicotinic acid (2-2)To a solution of methyl 2-chloro-5-iodonicotonate {2?_, 1.00 g, 3.36 mmol) in dimethylformamide (15 mL) at 25 C was added 3-chloro-5-methylboronic acid (0.573 g, 3.36 mmol; synthesized via procedures found in Org. Lett. 2007, P, 757-760), PdCl2dppf (0.246 g, 0.336 mmol) followed by IM aqueous cesium carbonate (13.5 mL, 13.5 mmol) and the system was stirred for 4h at 25 C. The system was partitioned between water and EtOAc, and dried over magnesium sulfate. Filtration and concentration yielded a brown solid which upon tritiration with ether afforded a tan solid. To this tan solid (0.05 g, 0.169 mmol) in dimethylformamide (0.8 mL) at 25 C was added l-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H pyrazole (0.038 g, 0.186 mmol), PdCl2dppf (0.012 g, 0.017 mmol) followed by 4M aqueous cesium carbonate (0.67 mL, 0.675 mmol) and the system was stirred for 15 minutes at 135 C in the microwave. The system was partitioned between water and EtOAc. The aqueous layer was then acidified using 25% citric acid to a pH of 3, extracted with EtOAc and the organic layer was dried over magnesium sulfate. Filtration and concentration afforded the title compound (2-2) as a cream solid. ESI+ MS [M+H]+ C17H14ClN3O2 = 328.0.

According to the analysis of related databases, 78686-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/20642; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem