Category: 14432-12-3

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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.Computed Properties of C5H5ClN2

Intermediate 252A: 2-chloro-5-iodopyridin-4-amine To a stirred solution of 2-chloropyridin-4-amine (5 g, 39 mmol) in DMF (50 mL) was added NIS (8.75 g, 39 mmol). The reaction mixture was then heated at 80 C for 3 h. The mixture was cooled and the DMF removed in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer was dried over Na2S04, filtered, and concentrated. The product was purified via column chromatography (10% EtO Ac/pet ether) to afford 2-chloro-5-iodopyridin-4-amine (4 g, 39% yield). LCMS: 254.8 (M+). Further elution with 12% EtO Ac/pet ether afforded 2- chloro-3-iodopyridin-4-amine (4 g, 39% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-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, Product Details of 14432-12-3, blongs to pyridine-derivatives compound. Product Details of 14432-12-3

2-Chloro-pyridin-4-ylamine 1b* (3.2 g, 0.025 mol) and sodium acetate (4.1 g, 0.05 mol) were stirred in acetic acid (20 ml). A solution of iodine monochloride (4.1 g, 0.025 mol) in acetic acid (10 ml) was added and the reaction mixture was heated to 70 C for approximately 3 h (NB: solution at -50 C, brown colour faded and precipitate formed as the reaction proceeded). The reaction mixture was cooled to room temperature, then poured onto water (700 ml), and extracted with EtOAc. The organic layer was carefully washed with a solution of Na2CO3 followed by a solution of Na2S2O3, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography using 10% EtOAc in DCM to yield 2-chloro-5-iodo-pyridin-4-ylamine 2b* (2.60 g, 40%). 1H NMR (400 MHz, CDCl3) delta (ppm): 8.34 (1 H, s), 6.63 (1 H, s), 4.78 (2 H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; ULLRICH, Axel; FALCENBERG, Mathias; WO2014/207260; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-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, Product Details of 14432-12-3, blongs to pyridine-derivatives compound. Product Details of 14432-12-3

2-Chloro-pyridin-4-ylamine 1b* (3.2 g, 0.025 mol) and sodium acetate (4.1 g, 0.05 mol) were stirred in acetic acid (20 ml). A solution of iodine monochloride (4.1 g, 0.025 mol) in acetic acid (10 ml) was added and the reaction mixture was heated to 70 C for approximately 3 h (NB: solution at -50 C, brown colour faded and precipitate formed as the reaction proceeded). The reaction mixture was cooled to room temperature, then poured onto water (700 ml), and extracted with EtOAc. The organic layer was carefully washed with a solution of Na2CO3 followed by a solution of Na2S2O3, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography using 10% EtOAc in DCM to yield 2-chloro-5-iodo-pyridin-4-ylamine 2b* (2.60 g, 40%). 1H NMR (400 MHz, CDCl3) delta (ppm): 8.34 (1 H, s), 6.63 (1 H, s), 4.78 (2 H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; ULLRICH, Axel; FALCENBERG, Mathias; WO2014/207260; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-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, 14432-12-3, blongs to pyridine-derivatives compound. name: 4-Amino-2-chloropyridine

Preparation 7: 2-Chloro-5-iodo-pyridin-4-ylamine N-lodosuccinimide (24.75 g, 110.0 mmol) was added to a solution of 2-chloro-pyridin-4-ylamine (12.85 g, 100.0 mmol) in acetonitrile (400 mL) and the mixture stirred and held at reflux overnight. Upon cooling to room temperature the solvent was removed in vacuo and residue partitioned between EtOAc (250 mL), saturated sodium thiosulfate (100 mL) andwater (250 mL). The organic layer was separated, washed with water (2 >< 250 mL), separated and the solvent removed in vacuo to afford an orange oil that was subjected to column chromatography on silica. Gradient elution with 30-50% EtOAc in petrol afforded a pale orange solid that was rinsed with 25% EtOAc in petrol (80 mL). Solids were collected by filtration and sucked dry to afford the title compound (7.32 g) as an off-white solid. Themother liquors were concentrated to dryness in vacuo and the residues subjected to columnchromatography on silica. Elution with 30-50% EtOAc in petrol afforded further pure material(1.90 g). Combined yield : (9.22 g, 36%) 1H NMR (DMSO-d6) 8.20 (1H, 5), 6.64 (1H, 5), 6.50(2H, br 5). MS: [M+H] 255. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common. Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; BUCK, Ildiko Maria; DAY, James Edward Harvey; HOWARD, Steven; SAXTY, Gordon; MURRAY, Christopher William; WO2014/60770; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14432-12-3, 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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 4-amino-2-chloropyridine (1.28 gm, 10 mmol) and di-tert-butyl dicarbonate (2.21 gm, 10.1 mmol) in THF (20 mL) was cooled to 00C and a solution of IM lithium bis(trimethylsilyl)amide in THF ( 20 mL, 20 mmol) was added slowly maintaining the temperature below 00C. The reaction was allowed to warm to room temperature over one hour and then quenched by the addition of 1.5 N aqueous ammonium chloride (15 mL). After stirring for several hours the reaction was extracted into ethyl acetate, washed with brine, the organic layer dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether give pure tert-butyl (2-chloropyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 25 – 45% ethyl acetate/ hexane to afford more product. EPO A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 gm, 5 mmol) in dry THF (20 mL) was cooled to -700C under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCtheta3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylrhoyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. 1H-NMR(5OO MHz, CDCI3): deltall.O (IH, br s), 10.52 (IH, s), 8.38 (IH, d, J= 6 Hz), 8.31 (IH, d, J= 6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

The chemical industry reduces the impact on the environment during synthesis 14432-12-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14432-12-3 ,Some common heterocyclic compound, 14432-12-3, molecular formula is C5H5ClN2, 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.

Preparation 13 : 2-Chloro-5-iodop; Silver sulfate (7.1g, 22.8mmol) and 4-amino-2-chloropyridine (4.06g, 31.6mmol) were added to a solution of iodine (5.65g, 22.3mmol) in ethanol (10OmL) and the reaction mixture stirred at rt for 72h. The bright yellow suspension was filtered, washed with methanol and the filtrate concentrated in vacuo. The residue was partitioned between saturated Na2CO3 solution (20OmL) and EtOAc (200ml). After separation the organic layer was washed with Na2S2O3 solution (5OmL, 25%) and brine (5OmL), dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with iso- EPO hexane/EtOAc (3:1 to 2.5:1) to give the title compound, delta? (CDCl3): 4.81 (2H, br s), 6.63 (IH, s), 8.38 (IH, s); m/z (ES+) = 254.86 [M+ H]+; RT = 2.51min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-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, 14432-12-3, blongs to pyridine-derivatives compound. name: 4-Amino-2-chloropyridine

10.3 Synthesis of 2-chloro-3-iodo-pyridin-4-ylamine 2a* 2-Chloro-pyridin-4-ylamine 1a* (3.2 g, 25 mmol) and sodium acetate (4.1 g, 50 mmol) were stirred in acetic acid (20 mL). A solution of iodine monochloride (4.1 g, 25 mmol) in acetic acid (10 mL) was added and the reaction mixture was heated to 70 C for approximately three h (NB: reaction mixture became a solution at ?50 C, the brown colour faded and a precipitate formed as the reaction proceeded). The reaction mixture was cooled to room temperature, then poured onto water (700 mL), and extracted with AcOEt (2 x 750 mL). The organic phase was carefully washed with a saturated aqueous solution of sodium carbonate (500 mL) followed by a 10% solution of sodium thiosulfate (500 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography using 10% AcOEt in DCM to yield 2-chloro-3-iodo-pyridin-4-ylamine 2a* (2.6 g, 41 %). 1H NMR (400 MHz, CDCl3) delta (ppm): 7.88 (1 H, d, J = 5.5 Hz), 6.46 (1 H, d, J = 5.5 Hz), 4.96 (2 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel (Prof. Dr.); Falcenberg, Mathias (Dr.); EP2818472; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14432-12-3, 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. 14432-12-3, name is 4-Amino-2-chloropyridine. A new synthetic method of this compound is introduced below.

NaHMDS (9 mL, 2 M, 18 mmol) was added dropwise to a solution of 2-chloro-4-aminopyridine (1.0 g, 7.8 mmol) in dry tetrahydrofuran (30 mL) at 0C under N2. After continuously stirred for 30 min, a solution of ditertbutyl dicarbonate (3.75 g, 17 mmol) in dry tetrahydrofuran was added. The reaction mixture was stirred overnight at room temperature, and then poured into saturated ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was washed by saturated brine, concentrated under vacuum to remove the solvent.The resulting residue was purified by column chromatography (petroleum ether :ethyl acetate = 8:1) to afford the title compound (923 mg, 36 %). 1H NMR (CDCl3): delta 8.39 (1H, d, J = 5.2 Hz), 7.19 (1H, d, J = 1.6 Hz), 7.05 (1H, dd, J = 1.6 Hz, 5.2 Hz), 1.47 (18H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); 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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.Safety of 4-Amino-2-chloropyridine

Under nitrogen protection, 2-chloropyridin-4-amine (301) (15 g, 0.116 mol, 1 eq) was dissolved in acetonitrile (200 mL) and heated to 70 C. in an oil bath, and then N-iodosuccinimide (NIS) (33 g, 0.139 mol, 1.2 eq) was added slowly. The reaction was stirred for 16 hours and cooled to room temperature. Saturated sodium thiosulfate solution was added until the reaction system turned to milk white. The pH of the reaction system was adjusted to 9-10 by an addition of saturated aqueous sodium carbonate solution and extracted with ethyl acetate (500 mL). The organic phase was separated which was washed with saturated brine (100 mL) twice, dried over anhydrous sodium sulfate, concentrated in vacuo and separated and purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=20/1) to obtain 2-chloro-5-iodopyridin-4-amine (23 g, yield: 78.1%). LCMS (ESI): m/z 255 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; GUANGZHOU BEBETTER MEDICINE TECHNOLOGY CO., LTD.; CAI, Xiong; QIAN, Changgeng; LI, Junqi; QING, Yuanhui; WANG, Yanyan; XUE, Weicai; YOU, Huajin; (23 pag.)US2018/297995; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14432-12-3 ,Some common heterocyclic compound, 14432-12-3, molecular formula is C5H5ClN2, 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.

A 50 mL single necked round bottom flask equipped with a magnetic stirrer bar,reflux condenser and nitrogen line was charged with 2-chloropyridin-4-amine 12 (2.50 g, 19.4 mmol, 1.0 equiv), sodiumacetate trihydrate (3.97 g, 29.2 mmol, 1.5 equiv), iodine monochloride(3.47 g, 21.4 mmol, 1.1 equiv) and glacial acetic acid(13.0 mL) and heated at 70 C with magnetically facilitated stirring under nitrogen for 16 h, at which point tlc and GC/MS (EI) analysisshowed that the starting material had been consumed. The reactionmixture was cooled and transferred to a separating funnel where itwas carefully quenched with portion wise addition of solidpowdered sodium hydrogencarbonate (32.3 g), water (75 mL) and ethyl acetate (75 mL). The resultant effervescence was allowed to subside and the mixture was not shaken. The layers were thenseparated and the aqueous layer was extracted with ethyl acetate(6 x 25 mL), with shaking. The organic layers were combined anddried over magnesium sulfate and the solvent was removed viarotary evaporation. The residue was purified by portionwise flashcolumn chromatography over silica using n-hexane/ethyl acetate(94:6 to 60:40) mixtures as eluent to give 2-chloro-3-iodopyridin-4-amine 13 as a light brown solid (2.21 g, 45%), a sample of whichhad 1H NMR spectral data and low resolution GC/MS (EI) massspectral data identical to those in the literature [12].

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. 14432-12-3, 4-Amino-2-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Balfour, Michael N.; Franco, Caio H.; Moraes, Carolina B.; Freitas-Junior, Lucio H.; Stefani, Helio A.; European Journal of Medicinal Chemistry; vol. 128; (2017); p. 202 – 212;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem