Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 108118-69-0, 2,6-Difluoropyridin-3-amine, 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: 2,6-Difluoropyridin-3-amine, blongs to pyridine-derivatives compound. Recommanded Product: 2,6-Difluoropyridin-3-amine

To a solution of 4-dimethylamino-benzoic acid (635 mg, 3.84 mmol) in CH2Cl2 (38 mL) was added l-chloro-N,N-2-triniethylpropenylamine (0.51 mL, 3.84 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (7.8 mL) before 2,6-difluoro-pyridin-3-ylamine (500 mg, 3,84) was added in one portion. After an additional 1 h, the reaction mixture was concentrated to dryness affording a residue to which was added DMF (5 mL) and K2CO3 (531 mg, 3.84 mmol). The resulting mixture was heated by microwave to 150 0C for 10 min, after which the resulting mixture was filtered, concentrated and purified by silica gel flash chromatography (0 to 100% EtOAc in hexanes) to afford [4-(5-fluoro-oxazolo[5,4-delta]pyridin-2-yl)-phenyl]-dimethyl-amine (430 mg, 1.67 mmol, 44%). ES MS (M+I-f) = 258; 1H NMR delta (ppm)(DMSO-d6): 8.28 (1 H, dd, J – 8.36, 7.14 Hz), 8.01-7.94 (2 H, m), 7.24-7.18 (1 H5 m), 6.87 (2 H, d, J = 8.89 Hz), 3.05 (6 H, s); HRMS m/z 258.1039 (C14H12FN3O + H+ requires 258.1037).

The synthetic route of 108118-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/155017; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1000025-07-9, Adding some certain compound to certain chemical reactions, such as: 1000025-07-9, name is Vadadustat,molecular formula is C14H11ClN2O4, 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 1000025-07-9.

Vadadustat (1 .0g), D-Proline (0.71 g) and methanol (16mL) were charged in a RBF at 25±5C and the contents were heated to 60-65C and stirred for 30-40 minutes at 60-65C. The reaction mass was slowly cooled to 25±5C and maintained under stirring at 25±5C for 16 hours. The product obtained was filtered, washed with prechilled methanol (1 mL) and dried under vacuum for 16 hours at 40C. The solid obtained was identified as 1 :1 co-crystal of Vadadustat D-Proline. Yield: 0.86g.

According to the analysis of related databases, 1000025-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; PILLI, Narasimha Murty; PATHURI, Srinivasarao; GOLIVI, Ramamohana Rao; JAYACHANDRA, Sureshbabu; (36 pag.)WO2020/75199; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936342-91-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride. A new synthetic method of this compound is introduced below.

A mixture of 5-bromo-2-chloromethylpyridine monohydrochloride(2.43g, 10mmol) and N-Boc piperazine (2.8g, 15mmol) was dissolved in N, N- dimethylformamide (20ml), followed by addition of potassium carbonate ( 4.84g, 35mmol), stirred at room temperature for 12 hours, 200ml of water was added to the reaction mixture was cooled, (100ml * 3) and extracted with ethyl acetate, then with saturated sodium chloride solution (100ml * 2) and washed, the resulting organic phase was dried over anhydrous magnesium sulfate and filtered, concentrated under reduced pressure to give 4- (5-bromo – pyridin-2-ylmethyl) – piperazine-1-carboxylate (3G, white solid), yield: 84percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,936342-91-5, 5-Bromo-2-(chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; SHANGHAI CDYMAX PHARMACEUTICALS CO., LTD; An, Xiaoxia; Bie, Pingyan; Liu, Jun; Yang, Wuli; (42 pag.)CN103360407; (2016); B;,
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 2546-56-7, name is 4-Chloro-3-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Example 306 Synthesis of 4-chloro-3-fluoropicolinaldehyde. To a solution of 2, 2, 6, 6-tetramethylpiperidine (35.4 g, 250.88 mmol) in 200 mL THF was added n-Butyllithium (2.4 M in hexane, 100 mL, 240 mmol) dropwise at 0 C. The reaction mixture was cooled to -78 C. after stirring at 0 C. for lh and a solution of 4-chloro-3-fluoropyridine (30.0 g, 228.08 mmol) in THF (100 mL) was added dropwise. The resulting reaction mixture was stirred at -78 C. for 2 h, a solution of DMF (17.5 g, 239.48 mmol) in THF (50 mL) was added dropwise, and the resulting reaction mixture was stirred at -78 C. for another 1 h. The reaction was quenched with H2O (50 mL), and extracted with ethyl acetate (200 mL*3). The combined organic layers were washed with brine, dried over with anhydrous magnesium sulphate, filtered, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=3/1) to afford 4-chloro-3-fluoropicolinaldehyde (26.0 g, yield: 71%). ESI-MS [M+H]+: 160.1.

With the rapid development of chemical substances, we look forward to future research findings about 2546-56-7.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89282-03-1, 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. 89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, 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.

C10 (3.5 g, 15.8 mmol) is added to a suspension of triphenylphosphine (166 mg, 0.63 mmol) and palladium acetate (71 mg, 0.32 mmol) in 25 mL DMF in dry flask under N2. Propioaldehyde diethyl acetal (2.3 mL, 15.8 mmol), cuprous iodide (120 mg, 0.63 mmol), and piperidine (1.6 mL, 16 mmol), are added successively, and the reaction is stirred 6 h at rt. The mixture is diluted with 125 mL EtOAc, is extracted with 4*50 mL 50% saturated 1:1 NaCl/NaHCO3, and the organic layer is dried over anhydrous Na2SO4 and then filtered. The dried organic layer is concentrated in vacuo to a dark oil. The crude material is chromatographed over 40 g silica gel (Biotage), eluding with 50% EtOAc/hexane. The fractions with the desired compound are combined and concentrated to afford 2-(diethoxymethyl)furo[3,2-c]pyridine (C11) (64% yield). HRMS (FAB) calculated for C12H15NO3+H: 222.1130, found 222.1123 (M+H)+.

According to the analysis of related databases, 89282-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1064783-29-4, name is 5-Chloro-3-fluoro-2-nitropyridine, molecular formula is C5H2ClFN2O2, 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. Product Details of 1064783-29-4

Compoud 271 (135 mg, 0.5 mmol) was dissolved in dry THF (15 mL) , and sodium hydride (60%, 24 mg, 0.6 mmol) was added at 0. The suspention was stirred for 10 minutes, then 33 (88 mg, 0.5 mmol) was added. The reaction mixture was stirred at room temperature for overnight, and then poured into brine. The resulting mixture was extracted with ethyl acetate. The combined organic layers were dried with anhydrous sodium sulfate, filtered and concentrated. The crude was purified by column chromatography to give light yellow solid (100 mg, 47%) . [0576] The obtained solid (100 mg, 0.24 mmol) was redissolved in methanol (10 mL) , and anhydrous ferric chloride (6 mg) , activated carbon (20 mg) was added. The mixture was refluxed for 15 minutes, then hydrazine hydrate (80%aqueous solution) (0.1 mL) was added dropwise. The resulting mixture was refluxed for 1 h, then poured into brine, and extracted with EA for three times. The combined organic layers were washed with brine once, dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the crude was purified by column chromatography to give white solid (85 mg, 89%) .

With the rapid development of chemical substances, we look forward to future research findings about 1064783-29-4.

Reference:
Patent; FUJIAN HAIXI PHARMACEUTICALS CO., LTD; FENG, Yan; WANG, Ruyong; LI, Junqing; ZHENG, Jianjia; LIAN, Xin; GONG, Xuan; FU, Yueli; KANG, Xinshan; (144 pag.)WO2019/174601; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52378-63-9, 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.52378-63-9, name is (3-Aminopyridin-2-yl)methanol, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

Example 59 5-Fluoro-N-(3-hydroxymethyl-pyridin-2-yl)-2-(3-methylsulfanyl-phenoxy)-nicotinamide 2-Hydroxymethyl-3-aminopyridine (89 mg, 0.716 mmol) and triethylamine (200 l, 2.14 mmol) were dissolved in dimethylformamide (1 ml) under nitrogen at room temperature and a solution of 5-Fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinic acid (200 mg, 0.716 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (151 mg, 0.788 mmol) and 1-hydroxybenzotriazole (106 mg, 0.788 mmol) in dimethylformamide (5 ml) and the reaction was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel eluding with a solvent gradient of dichloromethane:methanol:concentrated aqueous ammonia (97.5:2.5:0.25 changing to 95:5:0.5, by volume) and the product was crystallized from diisopropyl ether (5 ml) to give 5-Fluoro-N-(3-hydroxymethyl-pyridin-2-yl)-2-(3-methylsulfanyl-phenoxy)-nicotinamide (127 mg) as an off-white solid. 1H NMR (400 MHz, CDCl3): delta=8.14-8.16 (1H, d), 8.06-8,08 (1H, dd), 8.02-8.04 (1H, dd), 7.50-7.54 (1H, d), 7.28-7.32 (1H, t), 7.10-7.14 (1H, d), 6.97 (1H, s), 6.84-6.88 (1H, d), 6.46-6.50 (1H, d), 5.33 (2H, s), 4.89 (2H, brs), 2.45 (3H, s) ppm. LRMS (electrospray): m/z [M+H]+ 386, [M+Na]+ 408, [2M+Na]+ 793, [M-H]+ 384. Anal. Found C, 58.83; H, 4.16; N, 10.73. C19H16FN3O3S requires C, 59.21; H, 4.19; N, 10.90%.

Statistics shows that 52378-63-9 is playing an increasingly important role. we look forward to future research findings about (3-Aminopyridin-2-yl)methanol.

Reference:
Patent; Pfizer Inc; US2005/20587; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one, molecular formula is C5H3ClN2O3, 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. Recommanded Product: 850663-54-6

A) tert-butyl ((2S)-1-((4-chloro-5-nitropyridin-2-yl)oxy)propan-2-yl)carbamate To a solution of 4-chloro-5-nitropyridin-2-ol (1.00 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.51 g) and triphenylphosphine (2.25 g) in THF (10 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 4.52 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (860 mg). 1H NMR (300 MHz, CDCl3) delta 1.21-1.27 (3H, m), 1.44 (9H, s), 4.03-4.17 (1H, m), 4.37 (2H, dd, J=4.9, 1.5 Hz), 4.62 (1H, brs), 6.92 (1H, s), 8.86 (1H, s).

With the rapid development of chemical substances, we look forward to future research findings about 850663-54-6.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Yamashita, Tohru; Fujimoto, Takuya; Mizojiri, Ryo; Yonemori, Kazuko; Hirose, Hideki; Ikeda, Zenichi; Fujimori, Ikuo; Toyofuku, Kyoko; Yasuma, Tsuneo; Matsunaga, Nobuyuki; US2014/243310; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256561-65-5, 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 1256561-65-5, name is 3-(Bromomethyl)-5-fluoropyridine hydrobromide. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3 -(bromomethyl)-5 -fluoro-pyridine hydrobromide AA (53 mg, 0.19 mmol, 2.1 eq.) and sodium hydride (6.6 mg, 0.28 mmol, 3.0 eq.) in DMF (500 1iL) were stirred for 10 minutes. Compound Z (prepared according to methods described in Example 5) (25 mg, 0.092 mmol, 1.0 eq.) was added. After 18 hours, the reaction was diluted with ethyl acetate and washed with water and brine twice. The organic layerss were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by reverse phase HPLC afforded 12.8 mg (3 7%) of the title compound. ?H NMR (400 MHz, DMSO-d6) (5 8.47 (d, J= 2.8 Hz, 1H), 8.43 (s, 1H), 8.25 (s, 1H), 7.66 (s, 1H), 7.57- 7.53 (m, 2H), 7.36 (dd, J 1.92, 9.72 Hz, 1H), 7.29-7.25 (m, 2H), 4.41 (s, 2H), 3.49 (t, J= 5.2 Hz, 2H), 3.18 (t, J= 5.2 Hz, 2H), 2.76 (s, 3H); ES-MS [M+1]: 381.2.

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 1256561-65-5, 3-(Bromomethyl)-5-fluoropyridine hydrobromide.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P. Jeffrey; LINDSLEY, Craig, W.; EMMITTE, Kyle A.; FELTS, Andrew S.; BOLLINGER, Katrina A.; (140 pag.)WO2016/149324; (2016); 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. 72141-44-7, name is 4-Chloro-2-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

(e) 10.0 g (69.9 mmol) of the crude product of 4-chloro-2-methoxypyridine obtained in step (d) was dissolved in 100 mL of dimethylformamide, and 37.2 g (279 mmol) of N-chlorosuccinimide was added, followed by stirring at room temperature for 12 hours. 400 mL of water was added to terminate the reaction. Extraction with ethyl ether was carried out, then the organic layer was washed with a saturated sodium chloride aqueous solution, dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 9.10 g (crude yield 73%) of a crude product of 4,5-dichloro-2-methoxypyridine.1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 3.90(s, 3H), 6.85(s, 1H), 8.14(s, 1H)

The synthetic route of 72141-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1559320; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem