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. 59608-01-4, name is 3-(Pyridin-3-yl)propiolic acid, molecular formula is C8H5NO2, 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. Computed Properties of C8H5NO2

To a solution of D-2 (0.5 g, 3.4 mmol) in CH2CI2 (50mL) at 0C, Oxalyl chloride (0,86 g, 6.8 mmol) and 2 drops of DMF were added. The mixture was stirred at reflux over night. The solvent was removed to yield a light yellow oil.

With the rapid development of chemical substances, we look forward to future research findings about 59608-01-4.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2008/14311; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 917364-11-5, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, 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, Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid

Example 137N-((ls,4s)-4-(5-fluoro-2-(4′-(3-(piperazin-l-yl)propyl)biphenyl-3- yloxyJnicotinamidoJcyclohexylJ-S^^^-tetrahydroimidazo [ 1 ,2-a] pyridine-2- carboxamide To a solution of tert-butyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin- 2-yloxy)biphenyl-4-yl)propyl)piperazine-l-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added 5,6,7,8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (39.5 mg, 0.24 mmol) and triethylamine (0.331 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.159 mL, 0.25 mmol) was then added and the mixture stirred at RT for 1 h. The mixture was poured into sat NaHCO3 (aq) and the organics extracted into EtOAc (x2). The extractions were combined, dried (MgSO4) and evaporated to give a residue. This was dissolved in DCM (2 mL) to which TFA (2 mL) was added and the mixture stirred at RT for 20 min. The solvents were removed in vacuo and the residue dissolved in methanol and purified using reverse phase preparative chromatography using eluent = TFA(aq)/MeOH. The appropriate fractions were combined and evaporated to give a residue which on trituration with ether gave a solid. The solid was dried overnight under vacuum at 400C to give the title compound. Yield: 42 mg1H NMR (400 MHz, CD3OD) d 8.42 (d, J= 6.9 Hz, IH), 8.10 – 8.06 (m, 2H), 7.74 (s, IH), 7.53 (d, J= 8.2 Hz, 2H), 7.50 – 7.46 (m, 2H), 7.41 – 7.39 (m, IH), 7.28 (d, J= 8.2 Hz, 2H), 7.16 – 7.12 (m, IH), 4.15 – 4.08 (m, 3H), 3.98 – 3.91 (m, IH), 3.40 (t, J= 5.4 Hz, 4H), 3.21 – 3.16 (m, 4H), 2.97 – 2.89 (m, 4H), 2.72 (t, J= 7.4 Hz, 2H), 2.07 – 1.96 (m, 6H), 1.92 – 1.80 (m, 6H), 1.75 – 1.66 (m, 2H). MS: [M+H]+=680 (calc=680) (MultiMode+)

The synthetic route of 917364-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1256823-07-0, Adding some certain compound to certain chemical reactions, such as: 1256823-07-0, name is 5-Bromo-4-methoxypicolinonitrile,molecular formula is C7H5BrN2O, 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 1256823-07-0.

To a stirred solution of 4-methyl-1H-imidazole (580 mg, 7.04 mmol) in acetonitrile (24 mL) under an argon atmosphere were added potassium carbonate (1.3 g, 9.38 mmol) and 18-crown-6 (2.47 g, 9.38 mmol) at room temperature. The reaction mixture was stirred at 60 oC for 2 h. Then 5-bromo-4-methoxypicolinonitrile (1 g, 4.69 mmol) was added to the reaction mixture at room temperature. The reaction mixture was stirred at reflux for 18 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 90% EtOAc:hexanes to afford 4- methoxy-5-(4-methyl-1H-imidazol-1-yl) picolinonitrile (250 mg, 25%) as a yellow solid. 1H- NMR (CDCl3, 500 MHz): delta 8.58 (s, 1H), 7.82 (s, 1H), 7.39 (s, 1H), 6.99 (s, 1H), 401 (s, 3H), 2.23 (s, 3H); LCMS: 215 (M+1); (column; X-Bridge C-18 (50 × 3.0 mm, 3.5 mum); RT 2.45 min. 0.05% Aq TFA: ACN; 0.8 mL/min); TLC: EtOAc (Rf: 0.2).

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. 1256823-07-0, 5-Bromo-4-methoxypicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 71670-70-7, 2-(Chloromethyl)-5-methylpyridine hydrochloride, 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, HPLC of Formula: C7H9Cl2N, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9Cl2N

To 3,5-difluoro-4-nitrophenol (7.44 g, 42.5 mmol), Cs2CO3 (27.7 g, 84.9 mmol), and 2-(chloromethyl)-5-methylpyridine hydrochloride (7.6 g, 42.5 mmol) was added DMF (281 mL) and the reaction was stirred at 75 Celsius for 18 hours. The reaction was allowed to cool to room temperature before being poured into sat. NaHCO3. The aqueous phase was extracted three times with EtOAc, and the combined organic layers were washed four times with brine, dried (Na2SO4), filtered, and concentrated. The crude material was purified via FCC to afford the title compound. MS (ESI): mass calcd. for C13H10F2N2O3, 280.1; m/z found, 281.0 [M+H]+.

The synthetic route of 71670-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chai, Wenying; Dvorak, Curt A.; Eccles, Wendy; Edwards, James P.; Goldberg, Steven D.; Krawczuk, Paul J.; Lebsack, Alec D.; Liu, Jing; Pippel, Daniel J.; Sales, Zachary S.; Tanis, Virginia M.; Tichenor, Mark S.; Wiener, John J. M.; US2014/275029; (2014); 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 88312-64-5, name is Methyl 2-amino-5-nitronicotinate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H7N3O4

LiOH (0.12 g, 5 mmol) was added to a solution of the methyl ester 26a (1 g, 5 mmol) in a mixture of 1 % MeOH in THF (10 mL). The solution was stirred at room temperature for 17 h, then concentrated under reduced pressure. The solid obtained (0.8 g) was used in the next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 88312-64-5.

Reference:
Patent; UNIVERSITY OF DUNDEE; MEDIVIR AB; CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS; SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE; SYNGENE INTERNATIONAL LIMITED PLC; KAHNBERG, Pia; JOHANSSON, Nils-Gunnar; GILBERT, Ian; HAMPTON, Shahienaz; HARRISON, Justin; SARKAR, Sandipan; GONZALES, Dolores; WO2015/189595; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1211517-76-8, 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. 1211517-76-8, name is 3-Bromo-5-fluoro-4-methylpyridine. A new synthetic method of this compound is introduced below.

Step 2 3-Bromo-5-fluoro-4-methylpyridine (1.69 g, 8.89 mmol, Eq: 1.00), bis(triphenylphosphine)-palladium(10 dichloride (312 mg, 445 mumol, Eq: 0.05) and copper (I) iodide (84.7 mg, 445 mumol, Eq: 0.05) in DMF (15 ml) with flushed with nitrogen and treated with ethynyltrimethylsilane (1.05 g, 1.5 ml, 10.7 mmol, Eq: 1.2) and triethylamine (3.63 g, 5 ml, 35.9 mmol, Eq: 4.03). The reaction was heated to 115 C. and held at this temperature for 18 h. The mixture was cooled, diluted with water and extracted with ether (3*). The combined organic layers were washed with water (2*), brine, dried over anhydrous sodium sulfate, filtered through celite and concentrated to give a brown oil. The crude material was purified by flash chromatography (silica gel, 80 g, 20% EtOAc in hexanes). Fraction were pooled and evaporated to yield 1.09 g (59%) of 3-fluoro-4-methyl-5-((trimethylsilyl)ethynyl)pyridine as a yellow oil containing some solid. 1H NMR (DMSO-d6) delta 8.50 (s, 1H), 8.44 (s, 1H), 2.34 (d, J=1.8 Hz, 3H), 0.27 (s, 9H). LC-MS (ES) calculated for C11H14FNSi, 207.33. found m/z 207.8 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211517-76-8, 3-Bromo-5-fluoro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; DuBois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Thakkar, Kshitij Chhabilbhai; Wilhelm, Robert Stephen; US2013/109720; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1018505-59-3 ,Some common heterocyclic compound, 1018505-59-3, molecular formula is C11H18N4, 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-(2-Dimethylcarbonyl-2-carbonyl-ethylamino)-2-pyrimidinecarboxylic acid (1.26 g, 1.2 eq),5-(4-Ethyl-piperazin-1-yl)-piperidin-2-amino (0.81 g, 1 eq)And triethylamine (500 muL) in DMF (15 mL),Then HBTU (1.51 g, 1.5 eq) was added. The mixture was stirred at room temperature for 16 hours.Then with EtOAc (50 mL)And saturated NaHCO3 solution(15 mL), the layers were separated and EtOAc EtOAcThe combined organic layers were dried (MgSO4), filtered and evaporated.The residue was purified by column chromatography.1.04 g of the title compound 6 was obtained as a white solid(yield: 47%),Its nuclear magnetic resonance spectrum data is as follows:

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. 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Hu Xiande; Zhou Liming; Sui Guilan; (22 pag.)CN109568256; (2019); A;,
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 24207-22-5, name is 2-Bromo-3-methoxy-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 24207-22-5

To a solution of 2-bromo-3-methoxy-6-methylpyridine (2c) (310 g, 1.53 mol) in 6000 mL of water at 60 C was added KMnO, (725 g, 4.59 mol) in small portions over a 90 min period with vigorous mechanical stirring. A dark purple solution resulted. This solution was kept at 90 C for a further 3 h and filtered through Celite while still hot to give a colourless filtrate. After cooling, the aqueous solution was acidified to pH 1-2 by adding 6 N HCI. The white solid obtained was collected by filtration to give on drying 6-bromo-5-methoxy-2- pyridinecarboxylic acid (2d) (302g, 85%) of product, which was used as such in the next reaction without further purification. An analytical sample was obtained by recrystallization from methanol to give 6-bromo-5-methoxy-2-pyridinecarboxylic acid; 1H NMR (300 MHz, DMSO-tfe) delta 7.40 – 7.28 (m, 1H), 7.17 (d, J = 8.3 Hz, 1 H), 3.83 (d, J = 1.7 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 24207-22-5.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda S.; KAMATH, Vivekanand P.; GOWAN, Walter; (222 pag.)WO2016/29214; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 84539-34-4, Adding some certain compound to certain chemical reactions, such as: 84539-34-4, name is 4-Amino-3,5-dibromopyridine,molecular formula is C5H4Br2N2, 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 84539-34-4.

To a cooled (0 C) solution of 4-amino-3,5-dibromopyridine 12 (2.0 g, 7.94 mmol, 1.0 equiv) in 48% HBF4 aq (30 mL) was added dropwise NaNO2 (5.4 g, 79.4 mmol, 10 equiv) in water (16 mL) ensuring that no gas evolution could be detected. The resultant slurry was stirred at 0 C for 30 min. The reaction mixture was filtered to afford a white solid. The solid was quickly transferred portionwise to a stirred solution of KI (2.1 g, 12.7 mmol, 1.6 equiv) in 25 mL of acetone/H2O (2/3). The resultant brown slurry was decolorized with saturated Na2S2O3 and carefully neutralized with NaHCO3. The solution was then extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification by silica gel column chromatography (hexane/EtOAc = 10/1) yielded 5 (1.59 g, 4.38 mmol, 55%) as a colorless solid; Rf 0.61 (hexane/EtOAc = 5/1); mp 186-190 C; IR (KBr, cm-1) 1858, 1808, 1634, 1547, 1522, 1496, 1404, 1389, 1205, 1175, 1096, 1020, 883, 756, 687, 517, 422; 1H NMR (300 MHz, CDCl3) delta 8.56 (2H, s, H2/6); 1H NMR (300 MHz, DMSO-d6) delta 8.65 (2H, s, H2/6); 13C NMR (CDCl3, 75 MHz) delta 148.4, 129.9, 120.3; 13C NMR (75 MHz, DMSO-d6) delta 148.3, 129.4, 122.1; EI-MS (m/z) Calcd for C5H2Br2IN [M]+ 360.76. Found 360.75; EI-HRMS (m/z) Calcd for C5H2Br2IN [M]+ 360.7599. Found 360.7589.

According to the analysis of related databases, 84539-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Murakami, Yuko; Yanuma, Hiroto; Usuki, Toyonobu; Tetrahedron Asymmetry; vol. 23; 22-23; (2012); p. 1557 – 1563;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65147-89-9, 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. 65147-89-9, name is 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine. A new synthetic method of this compound is introduced below.

Example 238 Under an argon stream, a mixture of 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine (Compound of Reference Example 3) (90 mg), 2- (tributylstanyl) furan (305 mg), dichlorobis(triphenylphosphine)palladium(II) (23 mg) and N,N-dimethyl formamide (4 ml) was stirred at 80C for 24 hours.. The reaction mixture was poured into water and extracted with ethyl acetate – tetrahydrofuran (3: 1, v/v).. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure.. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate – chloroform – hexane (1: 1: 4, v/v) were concentrated under reduced pressure.. The resulting crystals were collected by filtration to obtain 6-(2-furyl)-2-phenyl-1H-imidazo[4,5-b]pyridine (49 mg, 57 %). HPLC (220 nm) Purity 100 % (Retention time 2.66 minutes) MS (APCI+, m/e) 262 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65147-89-9, 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1460067; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem