Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 588729-99-1, 3-Amino-5-bromo-2-chloropyridine, 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, COA of Formula: C5H4BrClN2, blongs to pyridine-derivatives compound. COA of Formula: C5H4BrClN2

EXAMPLE 32; N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)-2- fluorobenzenesulfonamide; (l)2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-3- amine.; (Some starting materials may be obtained from Aldrich, St. Louis, MO) To a 5 ml microwave tube was added 5-bromo-2-chloropyridin-3-amine (0.1 g, 0.5 mmol), bis(pinacolato)diboron (0.2 g, 0.7 mmol), potassium acetate (0.2 g, 2 mmol), 1,1′- bis(diphenylphosphino)ferrocene]dichloride palladium(ii) (0.03 g, 0.04 mmol), and dioxane (3 mL). The vial was sealed and placed in Biotage Initiator microwave (Biotage, Charlottesville,VA) for 20 min at 110 0C. LC/MS showed no sign of starting material. Dioxane was removed in vacuo. The residue was partitioned between EtOAc/water. The organic layer was washed with water, brine, dried over MgSO4 and removed solvent. The crude product was purified using SiO2 (12g) chromatography with hexanes_acetone=85%: 15% as the solvent system to afford the desired product as light yellow solid (75 mg). A peak at 38 min was collected. The solvent was concentrated to afford the desired product as light yellow solid (75 mg). MS (ESI pos. ion) m/z: calc’d for CHH16BCIN2O2: 254.1; found: 255.3 (M+l). 1H NMR (300 MHz, CHL0R0F0RM- d) delta ppm 1.35 (s, 12 H) 4.03 (br. s., 2 H) 7.40 (d, J=1.61 Hz, 1 H) 8.14 (d, J=1.61 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588729-99-1, 3-Amino-5-bromo-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
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. 166526-03-0, name is 4,6-Dichloronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4,6-Dichloronicotinonitrile

General procedure: At 0 C, to a suspension of sodium hydride (60% dispersion in oil, I 5 equiv) in DMF or DMA(080 moLL1), a solution of methyl ester B (tO equiv.) in DMF or DMA (0.65 moLL1) wasslowly added, foHowed after 15 minutes by a solution of nitrile A (11 equiv.) in DMF or DMA(0.65 moLL1). The reaction mixture was stirred at 70 C (oil bath) for 3 hours, before beingpoured into an ice cold saturated aqueous solution of NH4CI and extracted twice with CH2CI2.The organic layers were combined, washed with brine, dried over MgSO4, concentrated under vacuum and purified by flash column chromatography on silica gel (using a gradient of EtOAc in cyclohexane as eluent) to afford the product.

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, 166526-03-0, 4,6-Dichloronicotinonitrile.

Reference:
Patent; MAVALON THERAPEUTICS LIMITED; BLAYO, Anne-Laure; CATELAIN, Thomas; DORANGE, Ismet; GENET, Cedric; MANTEAU, Baptiste; MAYER, Stanislas; SCHANN, Stephan; (290 pag.)WO2018/206820; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 395652-44-5, 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.395652-44-5, name is 4-(Pyridin-2-yl)but-3-yn-1-ol, molecular formula is C9H9NO, molecular weight is 147.17, as common compound, the synthetic route is as follows.

A 0.23 M solution of 4-(2-pyridyl)-but-3-yn-1-ol (0.4 g, 2.72 mmol) in EtOH (12 mL)was passed through the H-Cube® hydrogenator flow reactor provided with 10percent Pd(OH)2 cartridge (flow rate: 1.0 mL/min; P = 1.0 bar, T = 25°C). The outcoming solution was concentrated to dryness, leading to the title compound (0.36 g, 88percent), which was used in the next step without any further purification. R = 1.11 mm. MS (ESI) mlz: 152 [M-H], 174 [M-Na].?H NMR (DMSO-d6): oe = 8.49?8.43 (m, 2H), 7.68 (td, 1H, J= 7.6, 1.9 Hz), 7.23 (d, 1H, J 7.6Hz), 7.18 (ddd, 1H, J= 7.6, 5.4, 1.9 Hz), 3.40 (t, 2H, J= 6.6 Hz), 2.71 (t, 2H, J= 6.6 Hz), 1.74?1.63 (m, 2H), 1.50?1.39 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 395652-44-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; PIOMELLI, Daniele; BANDIERA, Tiziano; BERTOZZI, Fabio; NUZZI, Andrea; FIASELLA, Annalisa; PONZANO, Stefano; PAGLIUCA, Chiara; REGGIANI, Angelo Mario; WO2014/144836; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86873-60-1, 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.86873-60-1, name is 5-Chloro-2-picolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

To a stirred suspension of (RS)-tert-butyl 3-(4-aminophenyl)pyrrolidine-1-carboxylate (200 mg, CAS 908334-28-1) in DMF (10 ml) were added sequentially N-methylmorpholine (0.22 ml), TBTU (490 mg) and 5-chloro-2-pyridine carboxylic acid (180 mg) and the mixture was stirred at room temperature for 90 min. The mixture was then diluted with ethyl acetate and washed sequentially with 1 M aq. hydrochloric acid and with saturated brine. The phases were separated and the organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-3-{4-[(5-chloro-pyridine-2-carbonyl)-amino]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (310 mg, quant.) as a white solid. MS (ISP): 421.3 ([M+NH4]+), 419.2 ([M+NH4]+).

Statistics shows that 86873-60-1 is playing an increasingly important role. we look forward to future research findings about 5-Chloro-2-picolinic acid.

Reference:
Patent; HOFFMANN-LA ROCHE INC.; Hoener, Marius; Raab, Susanne; Risterucci, Celine; Sewing, Sabine; US9132136; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1121-76-2, 4-Chloropyridine 1-oxide, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

4-(4-Chloro-benzyloxy)-py?dine-N-oxide: To a suspension of powdered potassium hydroxide (7.60 g, 136 mmol) and potassium carbonate (4.70 g, 34.1 mmol) in dry toluene were added (4-chloro-phenyl)-methanol (7.26 g, 50.9 mmol), 4-chloropyridinc-N-oxide (4.39 g, 34.0 mmol) and TDA-I (1.10 mL, 3.44 mmol). After the mixture was heated at reflux for 3 hours, the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified through a silica gel column to give 4-(4-chloro-benzyloxy)-pyridine-N-oxide in 40% yield as light yellowish solid. 1H NMR (CDCl1) 5: 8.13 (m, 2H), 7.37 (m, 4H), 6.85 (m, 2H), 5.06 (s, 2H); ESMS m/e: 235.9 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1121-76-2, 4-Chloropyridine 1-oxide, and friends who are interested can also refer to it.

Reference:
Patent; H. LUNDBECK A/S; WO2009/120655; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884495-03-8, 3-Amino-2-bromo-5-fluoropyridine, 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: 884495-03-8, blongs to pyridine-derivatives compound. Recommanded Product: 884495-03-8

General procedure: To a nitrogen-purged solution of aryl iodide in TEA (3 mL/mmol),DMF (3 mL/mmol) and MeOH (3 mL/mmol) was added Palladium (II)Acetate (0.03 eq)and Xantphos (0.06 eq). The reaction mixture was flushed with Carbon Monoxidegas for several minutes and then sealed with CO balloon attached and heated to 60C. for 3 hours. Upon completion, the reaction was cooled to room temperature and the crude product was triterated via addition of water and collected byfiltration. The crude intermediate was taken into the next step w/o furtherpurification.

The synthetic route of 884495-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58596-88-6 , The common heterocyclic compound, 58596-88-6, name is 2,6-Dichloro-3-methyl-5-nitropyridine, molecular formula is C6H4Cl2N2O2, 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.

(2e) 6-Chloro-5-methyl-3-nitro-2-pyridinamine [Formula 22]; A mixture of 2,6-dichloro-3-methyl-5- nitropyridine (10.41 g, 50.3 mmol), 28% aqueous ammonia solution (17 ml, 0.25 mol), potassium carbonate (10.4 g, 75.5 mmol) and t-butanol (167 ml) was stirred overnight at 60C under nitrogen atmosphere. After stirring at room temperature for 3 hours, a precipitate was filtered and then washed three times with water, thereby yielding the title compound (4.25 g, 22.7 mmol, 45%) as a yellow solid. ¹H NMR(400MHz, QMSO-D6) No. ppm; 2.23,(3H, s), 8.04(2H, br s), 8.39(1H, s).

The synthetic route of 58596-88-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 16250-08-1, name is 6-Aminopyridine-3-sulfonic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 6-Aminopyridine-3-sulfonic acid

(ii) Bromine (99 g, 0.62 mol) was added dropwise over 1 h, to a hot solution of the sulphonic acid (108 g, 0.62 mol) in water (600 mL) so as to maintain a steady reflux. Once the addition was complete the reaction was cooled and the resulting mixture filtered. The solid was washed with water and dried under suction to afford pyridine-2-amino-3-bromo-5-sulphonic acid (53.4 g). 1H NMR (DMSO-d6) delta: 8.08 (s, 1H), 8.14 (s, 1H).

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, 16250-08-1, 6-Aminopyridine-3-sulfonic acid.

Reference:
Article; Rawson, David J.; Ballard, Stephen; Barber, Christopher; Barker, Laura; Beaumont, Kevin; Bunnage, Mark; Cole, Susan; Corless, Martin; Denton, Stephen; Ellis, David; Floc’H, Marion; Foster, Laura; Gosset, James; Holmwood, Frances; Lane, Charlotte; Leahy, David; Mathias, John; Maw, Graham; Million, William; Poinsard, Cedric; Price, Jenny; Russel, Rachel; Street, Stephen; Watson, Lesa; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 498 – 509;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

A solution of 4-benzyloxy-2(1H)-pyridone (274 mg, 1.36 mmol), the iodide of preparation 10 (567 mg, 1.36 mmol), copper iodide (53 mg, 0.27 mmol), potassium carbonate (376 mg, 2.72 mmol) and rac-trans-N,N’-dimethyl cyclohexane-1,2-diamine (86 ml, 0.54 mmol) in 1,4-dioxan (10 ml) was degassed via a nitrogen/vacuum cycle. The resulting mixture was then heated to 100 C. under a nitrogen atmosphere for 16 hours. The reaction was cooled to room temperature and concentrated in vacuo. The residue was treated with 0.880NH3/H2O (10 ml, 1:1 v/v ratio) and stirred for 15 min. The resulting solid was filtered off and dried in vacuo giving the title compound (Prep. 11a/Ex. 23a) as a brown solid 550 mg (82%). 1H NMR (400 MHz, CDCl3) delta ppm 1.13 (t, 3H), 1.43 (s, 9H). 2.09-2.25 (m, 2H), 3.12-3.30 (m, 2H), 3.31 (t, 1H), 3.40 (q, 1H), 3.65 (q, 2H), 4.60-4.77 (m, 1H), 5.01 (s, 2H), 6.00-6.01 (m, 2H), 6.40 (d, 1H), 7.18 (d, 1H), 7.30-7.41 (m, 5H), 7.48 (dd, 1H), 8.03 (d, 1H). LRMS m/z (ESI) 491 [MH+].

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2008/85884; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 96568-04-6, Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, 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 Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, blongs to pyridine-derivatives compound. Application In Synthesis of Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate

[ETHYL-3- (2, 6-DICHLORO-5-FLUOROPYRIDINYL)-3-OXO-PROPANOATE] (5 g, 18 mmol) is mixed with triethyl orthofomate (4.3 [ML,] 26 mmol) and acetic anhydride (4.1 [ML,] 43 mmol) and the mixture is heated at reflux for 2 hours. The mixture is then concentrated under vacuum to afford the desired product.

The synthetic route of 96568-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE PROCTER & GAMBLE COMPANY; WO2004/14893; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem