Category: pyridine-derivatives

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. 1072-97-5, name is 5-Bromopyridin-2-amine, molecular formula is C5H5BrN2, 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. Safety of 5-Bromopyridin-2-amine

Example 57b. 5-(l-Methyl-lH-pyrazol-4-yl)-pyridin-2-ylamineA mixture of 2-amino-5-bromopyridine (3.0 g, 17.3 mmol), l-methyl-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2yl)-lH-pyrazole (5.4 g, 26.0 mmol) and potassium carbonate (3.6 g, 26.0 mmol) in dimethoxy ethane (60 mL) and water (10 mL) was degassed for 15 minutes using nitrogen. [l,l ‘-Bis(di-tert-butylphosphino)- ferrocene]palladium (II) dichloride (562 mg, 0.87 mmol) was added and the reaction mixture was heated in a sealed tube at 90 0C overnight. The mixture was cooled to room temperature and partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic phase was separated and the aqueous layer was re-extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using a gradient of 2 to 5% methanol in dichloromethane. The desired fractions were collected and concentrated in vacuo, and the solid obtained was washed with diethyl ether to offord the title compound (2 g, 66%).1H NMR (400 MHz, CHLOROFORM-d) delta ppm 3.94 (s, 3 H) 4.39 (br. s., 2 H) 6.53 (d, J=8.21 Hz, 1 H) 7.50 (m, 2 H) 7.66 (s, 1 H) 8.21 (d, J=2.34 Hz, 1 H). ESMS m/z: [M+l]+ 175.1

With the rapid development of chemical substances, we look forward to future research findings about 1072-97-5.

Reference:
Patent; ASTRAZENECA AB; LO-ALFREDSSON, Yvonne; PAULSEN, Kim; RAKOS, Laszlo; ROTTICCI, Didier; WALDMAN, Magnus; WO2010/132015; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75711-00-1, 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 75711-00-1, name is 2-Chloro-3-methoxy-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 3-methoxy-2-(4-methyl-1H-imidazol-1-yl)-5-nitropyridine To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (2 g, 10.60 mmol) in DMSO (40 mL) under an argon atmosphere were added potassium carbonate (3.65 g, 26.51 mmol) and 4-methyl-1H-imidazole (1 g, 12.72 mmol) at room temperature. The reaction mixture was stirred at 45 C. for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (40 mL) to obtain solid which was filtered and dried in vacuo to afford 3-methoxy-2-(4-methyl-1H-imidazol-1-yl)-5-nitropyridine (1.8 g, 72%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.92-8.90 (m, 1H), 8.45 (s, 1H), 8.36-8.32 (m, 1H), 7.68 (s, 1H), 4.10 (s, 3H), 2.20 (s, 3H); LC-MS: 235 (M+1); (column; X-Bridge C-18 (50*3.0 mm, 3.5 mum); RT 2.09 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/CH2Cl2 (Rf: 0.4).

According to the analysis of related databases, 75711-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56129-55-6, Adding some certain compound to certain chemical reactions, such as: 56129-55-6, name is 1-(Pyridin-3-yl)ethanamine,molecular formula is C7H10N2, 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 56129-55-6.

Example 46 5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-(methyl-pyridin-3-ylmethyl-amino)-thiazol-4-one 5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-(methyl-pyridin-3-ylmethyl-amino)-thiazol-4-one was prepared from 5-[1-(4-chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-propylsulfanyl-thiazolidin-4-one and Methyl-pyridin-3-ylmethyl-amine following General Procedure B. 1H NMR (400 MHz, DMSO) delta 8.62 (dd, 1H), 8.57 (dd, 0.4H), 8.55 (dd, 0.6H), 8.34 (d, 0.6H), 8.31 (d, 0.4H), 8.16-8.14 (m, 1H), 7.89-7.8 (m, 1H), 7.83 (s, 1H), 7.79-7.75 (m, 2H), 7.72-7.68 (m, 1H), 7.67-7.63 (m, 1H), 7.46-7.41 (m, 1H), 6.78-6.75 (m, 1H), 5.86 (s, 2H), 5.01 (s, 0.6H), 4.90 (s, 0.4H), 3.29 and 3.28 (2s, 3H, rotamers). LC/MS (m/z) [M+1]+ 542.1 (calculated for C26H19ClF3N5OS, 541.1).

According to the analysis of related databases, 56129-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIGNAN, Gilles; Gaul, Micheal; Xu, Guozhang; Zhao, Bao-Ping; US2011/200586; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 769-28-8 ,Some common heterocyclic compound, 769-28-8, molecular formula is C8H8N2O, 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.

[00176] Step 2: tert-butyl ((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3- yl)methyl)carbamate: To a solution of 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3- carbonitrile (40 g, 0.27 mol) in THF/CH30H (1:1, 2 L) were added Ni (40 g), Boc20 (110 g,0.5 mol) and Et3N (50 g, 0.5 mol). Then the mixture was stirred in H2 atmosphere at roomtemperature for 48 h. The reaction solution was filtrated and concentrated to give crude product. The crude was added H20 (200 mL) and extracted by DCM (600 mL*3). The organic layer was concentrated to give tert-butyl ((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3- yl)methyl)carbamate (40 g, 56 %) for next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,769-28-8, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NASVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2015/23915; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1123194-98-8 , The common heterocyclic compound, 1123194-98-8, name is 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine, molecular formula is C10H10BrN3O, 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 solution6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl) pyridine (20 g, 74 mmol) in DMF (240 mL) at room temperature under an argon atmosphere were added Pd(dppf)2C12 (500 mg, 0.9 mmol), Pd2(dba)3 (682 mg, 0.7 mmol) and zinc cyanide (5.3 g, 45 mmol). The reaction mixture was stirred at 140 C for 2 h. After consumption of starting material (monitored by TLC), the reaction mixture was diluted with 25% NH4OH solution (240 mL) to afford the solid. The solid was collected by filtration and dried in vacuo to afford 6-methoxy-5-(4- methyl-1H-imidazol-1-yl) picolinonitrile (14 g, 88%) as a pale yellow solid.[0872] ?H NMR (CDC13: 400 MHz): 7.89 (s, 1H), 7.63 (d, 1H), 7.43 (d, 1H), 7.01 (s, 1H), 4.09 (s, 3H), 2.30 (s, 3H); LCMS: 98.7%; 214.9 (M+1); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 pm); RT 1.19 mm; mobile phase: 0.025% Aq TFA+5% ACN:ACN+5% 0.025% Aq TFA; T/B%: 0.0 1/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: EtOAc (R1 0.3).

The synthetic route of 1123194-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-12-1 ,Some common heterocyclic compound, 74115-12-1, molecular formula is C5H4ClNO, 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.

33b. 3-Chloro-2-(4-nitrophenylazo)-5-hydroxypyridine To a solution of 5-chloro-3-pyridinol (20.0 g, 0.154 mol, Aldrich) and KOH (13.0 g, 0.232 mol) in 300 mL of water at 0 C. was added p-nitrobenzenediazonium tetrafluoroborate (36.6 g, 0.154 mol, Aldrich). After 1 hour, 50 mL of glacial acetic acid was added, and the bright red precipitate was filtered and air-dried. Chromatography (silica gel; CH2 Cl2 /MeOH, 95:5-90:10) afforded the title compound as a bright red solid (28.8 g, 67%): 1 H NMR (DMSO-d6, 300 MHz) delta 7.14 (d, J=2.4 Hz, 1H), 7.89 (d, J=2.4 Hz, 1H), 8.00 (m, 2H), 8.39 (m, 2H); MS (CI/NH3) m/z: 279, 281 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74115-12-1, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6133253; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 40673-25-4 , The common heterocyclic compound, 40673-25-4, name is 4-Chloro-2-hydroxypyridine, molecular formula is C5H4ClNO, 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-Chloro-2-hydroxy-pyridine (247 mg, 1.91 mmol), Ag2CO3 (1.58 g, 5.74 mmol) and MeI(0.13 ml, 2.11 mmol) were heated in a sealed tube at 50 0C for 16 hours and then filtered through celite and concentrated at reduced pressure. The residue was purified by FCC (Pentane/Diethyl ether with gradient, 99:1 to 95:5) to provide the title compound as colourless oil (160 mg, 58%).LCMS data: Calculated MH+ (144); Found 100% (MH+) m/z 144, Rt = 1.71 min.NMR data: 1H NMR (500 MHz, CDCl3) delta ppm 8.07 (1 H, d, J=5.5 Hz), 6.89 (1 H, dd, J=5.5,1.5 Hz), 6.77 (1 H, d, J=1.7 Hz), 3.94 (3 H, s).

The synthetic route of 40673-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/135842; (2009); A1;,
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.916325-85-4, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H4BrN3O2, molecular weight is 242.03, as common compound, the synthetic route is as follows.name: 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

To a solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XXXIV) (1.6 Kg, 6.6 mol) in anhydrous MeOH (32 L) was added H2SO4 (160 mL). The reaction was slowly heated to 70oC and stirred for 20 hours. The solution was concentrated under vacuum to a volume of 1.6 L. The residue was partitioned between DCM (120 L) and aqueous 10% NaHCO3 (32 L). The organic phase was separated and washed with aqueous 25% NaCl (32 L), dried over Na2SO4 and concentrated to a volume of 4.8 L. The product was crystallized by charging the solution with 3 x n-heptane (8 L) while concentrating the volume to 4.8 L after each addition of n- heptane. The solid was filtered and dried under vacuum at 50oC to produce methyl 5-bromo-1H- pyrazolo[3,4-b]pyridine-3-carboxylate (XXXV) (1.53 Kg, 6.0 mol, 80.6% purity, 90.4% assay yield).1H NMR (DMSO-d6, 400 MHz) d ppm 3.95 (s, 3H), 8.62 (d, J=2Hz, 1H), 8.73 (d, J=2.4Hz, 1H), 14.78 (brs, 1H); ESIMS found C8H6BrN3O2 m/z 256.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,916325-85-4, 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; MITTAPALLI, Gopi Kumar; CHIRUTA, Chandramouli; HOFILENA, Brian Joseph; (128 pag.)WO2019/241540; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 393-53-3 ,Some common heterocyclic compound, 393-53-3, molecular formula is C6H4FNO2, 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.

Step 1 : Synthesis of 3-[(4-iodo-2-fluoro)amino]isonicotinic acid.; 3-Fluoro-isonicotinic acid (1g, 7.09mmol) and 4-iodo-2-fluoroaniline (1.68g, 7.09mmol) was added to 10mI of dry THF and the mixture was cooled to -78C. LiHMDS (1 M in THF, 24.8ml) was added and the mixture was al lowed to warm to room temperature over night. Solid ammonium hydrochloride (2g) was added and after 1h the mixture was filtered and the volatiles were removed in vacuo. The crude material was purified by flash-chromatography using C2-modified silica a nd a gradient of 0-12% methanol in DCM as eluent to give 932mg (2.32mmol; 33% yield) of pure desired carboxylic acid 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. 393-53-3, 3-Fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/45514; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-35-7, 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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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 solution of commercially available 5-bromo-1H-pyrrolo[2,3-b]pyridine (5.60 g, 28.4 mmol) in CH2Cl2 (25 mL) was added N-iodosuccinimide (7.67 g, 34.1 mmol). The reaction mixture was stirred at ambient temperature for 2 h. The precipitate was filtered and washed with cold CH2Cl2 (2*5 mL) to provide the title compound as a light tan solid (7.17 g, 78% yield) which was used as is in the next step without further purification: MS (ES) m/z 323 (M+H).

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 183208-35-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; Jacobsen, Eric Jon; Blinn, James Robert; Springer, John Robert; Hockerman, Susan L.; Anderson, David Randolph; (120 pag.)US2018/208594; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem