Category: 69045-79-0

Reference of 69045-79-0, 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. 69045-79-0, name is 2-Chloro-5-iodopyridine. A new synthetic method of this compound is introduced below.

Zinc dust (127mg, 1.94mmol, 1.1eq) was dried for 18h at 100C in vacuo, transferred to a round bottomed flask and heated with a hot air gun under vacuum. The flask was allowed to cool to room temperature and DMF (2ml) and 1,2-dibromoethane (12mul, 0.141mmol, 0.08eq) added. The mixture was heated to 70C for 10 mins, allowed to cool to r. t., and TMSCI (18mul, 0.141mmol, 0.08eq) added dropwise. This mixture was stirred at r. t. for 30min before dropwise addition of 3-iodoazetidine-1-carboxylic acid tert-butyl ester (Ref SynLett, 1998,4, 379)(500mg, 1.766mmol, 1.Oeq) as a solution in DMF (2ml). The mixture was stirred at 40C for 1 h. 2-chloro-5-iodopyridine was dissolved in DMF (2ml) and added, followed by Pd2dba3 (32mg, 0.035mmol, 0.02eq) and tri-2-furylphosphine (17mg, 0.071mmol, 0.04eq) and the mixture heated to 70C for 4h. The mixture was allowed to cool, diluted with Et20(40ml) and NH4CI (40ml, sat’d aq), layers separated, the aqueous layer was re-extracted with Et20(20ml), organics combined, washed with brine (2x30ml), dried (MgS04), filtered and evaporated to give a yellow solid. This solid was flash chromatographed on silica gel with a gradient elution from 100% CH2CI2 to 99: 1 CH2CI2:MeOH to give 235mg of impure product. This material was further purified by fish chromatography on silica get with a gradient elution from 100% toluene to 95:5 toluene:EtOAc to give the title compound as a yellow solid (193mg, 41%) Tlc Rf = 0.13 (10%EtoAc/Toluene UV visualisation) MS (APCI+) 269 (MH+) ¹H NMR: No.H (400 MHz, CDCI3) 8.3 (1 H, s), 7.7 (1 H, m), 7.35 (1 H, d), 4.35 (2H, t), 3.9 (2H, t), 3.65-3.8 (1 H, m), 1.45 (9H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69045-79-0, 2-Chloro-5-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/115985; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69045-79-0 , The common heterocyclic compound, 69045-79-0, name is 2-Chloro-5-iodopyridine, molecular formula is C5H3ClIN, 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.

Synthesis of 2-hydrazinyl-5-iodopyridine (0815) The solution of 2-chloro-5-iodopyridine (2.0 g, 20.9 mmol), anhydrous hydrazine (3.3 mL, 105 mmol) in pyridine (40 mL) was heated at reflux overnight. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added 1 N sodium hydroxide solution and it was extracted with EtOAc. The organic layer was separated, dried (sodium sulfate) and concentrated under reduced pressure. To the residue was added hexanes, and the precipitate was collected and dried in vacuo to afford the title compound (1.35 g, 69% yield) as off-white crystals. MS (ES+, m/z): 236.2 (M++1).

The synthetic route of 69045-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tolero Pharmaceuticals, Inc.; Xu, Yong; Brenning, Benjamin Gary; Kultgen, Steven G.; Liu, Xiaohui; Saunders, Michael; Ho, Koc-Kan; (119 pag.)US9416132; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69045-79-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 69045-79-0 as follows.

2-Chloro-5-iodopyridine (0.20 g, 0.83 mmol) was stirredfor 5h at 120C in pyridine with hydrazine hydrate (0.25mL,4.17 mmol). The solvent was removed under reduced pressureand the residue dissolved in AcOEt and extracted withwater. The organic layer was dried over Na2SO4 and concentratedto dryness to give 9a (0.19 g, 90%). IR (ATR, cm-1)3248; 3158; 2983; 1586; 1506; 1476; 1075; 805. 1H NMR(CDCl3) 8.26 (s, 1H); 7.67 (d, 1H, J= 9 Hz); 6.59 (d, 1H,J= 9 Hz). 13C NMR (CDCl3) 160.3; 153.5; 145.2; 109.3;78.5. MS (ESI+) [M+H]: 236.20. HRMS (ESI+) [M+H]+:235.9691 observed, 235.9685 calculated for C5H7IN3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-79-0, its application will become more common.

Reference:
Article; Joyard, Yoann; Bischoff, Laurent; Levacher, Vincent; Papamicael, Cyril; Vera, Pierre; Bohn, Pierre; Letters in Organic Chemistry; vol. 11; 3; (2014); p. 208 – 214;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-79-0, 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 69045-79-0, name is 2-Chloro-5-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (S)-1-(phenyl-3-boronic acid)-ethyl]-carbamic acid tert-butyl ester (1.29 g, 4.86 mmol) and 2-chloro-5-Iodo-pyridine (1.4 g, 11.4 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (4.75 g, 14.6 mmol) and water (5 mL). Argon was bubbled in to the above mixture for 10 min, and Pd(PPh3)4 (280 mg, 0.24 mmol) was added. The reaction mixture was stirred at 100 C. for 18 hand then cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2¡Á100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (785 mg, 69%) as yellow oil. [0147] 1H NMR (DMSO d6, 400 MHz): delta 1.28 (d, 3 H, J=6.8 Hz), 4.04 (q, 1 H, J=6.8 Hz), 7.4-7.45 (m, 2H), 7.5-7.55 (m, 1H), 7.61 (d, 1H J =7.8 Hz,), 7.72 (s, 1H), 8.15 (dd, 1H, J=8.3, 2.5 Hz,), 8.73 (d, 1H, J=3.3 Hz).

According to the analysis of related databases, 69045-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wu, Yong-Jin; Sun, Li-Qiang; L’Heureux, Alexandre; US2004/110754; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69045-79-0, 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.69045-79-0, name is 2-Chloro-5-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.4415, as common compound, the synthetic route is as follows.

General procedure: In a glove box, a flame-dried pressure Schlenk tube was charged with NaI(0.3 equiv). The Schlenk tube was taken out of the glove box and charged with amide 1 (1.5equiv), iodopyridine reagent (1 equiv), Ag2CO3 (1.5 equiv), (BnO)2PO2H (0.2 equiv) andPd(OAc)2 (0.1 equiv). DMA and Toluene (1:20 in v/v ratio, 0.1 M) were added. The tube wastightly closed and flushed with argon by three freeze-pump-thaw cycles. The mixture was stirredat 130 C for 24 h. Subsequently, it was diluted with EtOAc (40 mL) and washed with brine (2 ¡Á20 mL) and water (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated invacuo. The crude product was purified by flash chromatography (hexane/ EtOAc in 85/15 to 50/50v/v ratio). Unless otherwise noted, the reactions were run on 0.1 mmol scale.

Statistics shows that 69045-79-0 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-iodopyridine.

Reference:
Article; Hu, Peng; Bach, Thorsten; Synlett; vol. 26; 20; (2015); p. 2853 – 2857;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem