Category: 153034-86-7

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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Chloro-4-iodopyridine

Intermediate 1; 4-Iodo-1H-pyridin-2-one; To 10.0 g (41.8 mmol) 2-chloro-4-iodopyridine in 100 mL AcOH are added 17.1 g (208 mmol) NaOAc and the reaction mixture is heated at 180 C. for 2 h in a microwave oven. DCM and water are added to the reaction mixture and the layers are separated. The organic layer is washed with water, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is triturated with TBME.C5H4INO (M=221.0 g/mol),ESI-MS: 222 [M+H]+ Rf (TLC): 0.3 (silica gel DCM/MeOH 9/1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153034-86-7, 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 153034-86-7, name is 2-Chloro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a glovebox, aryl iodide (1.0 mmol), CsF (228 mg, 1.5 mmol), and CuI (19.0 mg, 0.1 mmol) were weighed into a 4-dram borosilicate scintillation vial and dissolved in DMF (5 mL). Aryltriethoxysilane (1.0 mmol) was then added to the mixture, and the vial was tightly capped with a poly-seal cone-lined urea cap (Wheaton). The mixture was taken out of the glovebox and placed in an oil bath preheated to 120 C with vigorous stirring. After 48 h, the mixture was cooled to r.t., diluted with EtOAc (15 mL), and washed with H2O (2× 5 mL). The aqueous fraction was back-extracted with EtOAc (3 ×5 mL). The combined organic fractions were dried (Na2SO4) and cotton-filtered, and the solvent was removed on a rotary evaporator. The product was purified by column chromatography (silica gel, hexanes, hexanes-Et2O, or hexanes-EtOAc).

According to the analysis of related databases, 153034-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gurung, Santosh K.; Thapa, Surendra; Shrestha, Bijay; Giri, Ramesh; Synthesis; vol. 46; 14; (2014); p. 1933 – 1937;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-86-7, 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. 153034-86-7, name is 2-Chloro-4-iodopyridine. A new synthetic method of this compound is introduced below.

Step 1: 2-CHLORO-4-TRIMETHYLSILANYLETHYNYL-PYRIDINE 2-Chloro-4-iodo-pyridine (10.0 g, 41.8 mmol) was dissolved in 200 mL of dry THF and 17.5 mL of triethyl amine. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (329 mg, 1.25 mmol) and bis (triphenylphosphine) palladium (II) chloride (1.47 g, 2.09 mmol) were added and the reaction mixture was stirred at room temperature for lh. Copper (I) iodide (239 mg, 1.25 mmol) and trimethylsilylacetylene (6.28 g, 6.39 mmol) were added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in 500 mL of water and extracted three times with ethyl acetate (500 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (cyclohexane/ethyl acetate 80: 20). The desired product was obtained as a light brown semi solid (10 g, >100%). This material was used without any further purification for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/3117; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-86-7, 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. 153034-86-7, name is 2-Chloro-4-iodopyridine. A new synthetic method of this compound is introduced below.

Step 1: 2-CHLORO-4-TRIMETHYLSILANYLETHYNYL-PYRIDINE 2-Chloro-4-iodo-pyridine (10.0 g, 41.8 mmol) was dissolved in 200 mL of dry THF and 17.5 mL of triethyl amine. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (329 mg, 1.25 mmol) and bis (triphenylphosphine) palladium (II) chloride (1.47 g, 2.09 mmol) were added and the reaction mixture was stirred at room temperature for lh. Copper (I) iodide (239 mg, 1.25 mmol) and trimethylsilylacetylene (6.28 g, 6.39 mmol) were added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in 500 mL of water and extracted three times with ethyl acetate (500 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (cyclohexane/ethyl acetate 80: 20). The desired product was obtained as a light brown semi solid (10 g, >100%). This material was used without any further purification for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/3117; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153034-86-7 ,Some common heterocyclic compound, 153034-86-7, 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.

Step 1 To a solution of 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (681 mg, 3.51 mmol) and 2-chloro-4-iodopyridine (700 mg, 2.92 mmol) in 1,4-dioxane (12 mL) was added 2.0 M aqueous Na2CO3 (4.39 mL, 8.77 mmol) and tetrakis(triphenylphosphine)palladium(0) (67.6 mg, 0.059 mmol). The reaction mixture was heated at 90 C. for 3.5 h then cooled to room temperature, diluted with water and extracted with EtOAc (2*). The combined organics were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (0% to 10% EtOAc/hexanes) to afford 450 mg (86%) of 2-chloro-4-cyclopent-1-enyl-pyridine as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-86-7, its application will become more common.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153034-86-7, 2-Chloro-4-iodopyridine, 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, 153034-86-7, blongs to pyridine-derivatives compound. name: 2-Chloro-4-iodopyridine

General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2×20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5% EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-86-7, its application will become more common.

Reference:
Article; Rao, Maddali L.N.; Dhanorkar, Ritesh J.; Tetrahedron; vol. 71; 2; (2015); p. 338 – 349;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153034-86-7 , The common heterocyclic compound, 153034-86-7, name is 2-Chloro-4-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.

(S)-5-(3-Bromophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (243 mg, 0.599 mmol) obtained in Step 1 of Example 13 was dissolved in 1,4-dioxane (7 mL), and the mixture was stirred at 100C for 2 hours after adding bis(pinacolato)diboron (0.380 g, 1.50 mol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 98.0 mg, 0.120 mmol), and potassium acetate (0.295 g, 3.00 mmol). The reaction mixture was filtered through sellite, and the filtrate was diluted withy ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography. The resulting crude product was dissolved in 1,4-dioxane/water = 4/1 (12.5 mL), and the mixture was stirred at 100C for 3 hours after adding 2-chloro-4-iodopyridine (216 mg, 0.902 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 49.0 mg, 0.060 mmol), and sodium carbonate (191 mg, 1.80 mmol). The reaction mixture was then filtered through sellite, and the filtrate was extracted with ethyl acetate. The organic layer was then washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by silica gel column chromatography to give 5-[3-(2-chloropyridin-4-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro5,8,10,10b-tetraazabenzo[e]azulen-6-one (113 mg, 43% (2 steps)). ESI-MS: m/z 438 [M + H]+. 1H NMR (CDCl3) delta(ppm) : 1.70 (m, 1H), 1.94 (m, 1H), 2.10 (m, 1H), 2.25 (m, 1H), 2.56 (s, 3H), 3.82-3.95 (m, 4H), 4.40 (m, 1H), 7.35 (dt, J = 2.02, 7.33 Hz, 1H), 7.43 (dd, J = 1.65, 5.31 Hz, 1H), 7.51-7.59 (m, 4H), 8.44 (d, J = 5.32 Hz, 1H), 8.87 (s, 1H).

The synthetic route of 153034-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153034-86-7, 2-Chloro-4-iodopyridine, 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, Formula: C5H3ClIN, blongs to pyridine-derivatives compound. Formula: C5H3ClIN

l-Bromo-3-ethynylbenzene (3.76 g, 20.77 mmol), palladium(II) dicMorobis(triphenylphosphine) (73 mg, 0.10 mmol) and copper(I) iodide (0.020 g, 0.10 mmol) were dissolved in anhydrous tetrahydrofuran (15 mL) and triethylamine (10 mL). 2- Chloro-4-iodorhoyridine (4.97 g, 20.77 mmol) dissolved in anhydrous tetrahydrofuran (5 mL) was added. The reaction was stirred at room temperature over night under an atmosphere of nitrogen. The reaction was quenched with hydrochloric acid (2M aq.) and extracted with dichloromethane twice. The aquous phase was then made basic using NaOH (15% aq.) and extracted with dichloromethane twice. The combined organic phases were concentrated in vacuo and the product was purified by column chromatography using a gradient eluent (0 to 30% ethyl acetate in heptane) to give 5.38 g (89% yield) of the title compound: MS (ESI) m/z 294 [M+l]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2008/76046; (2008); 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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Chloro-4-iodopyridine

Method 2: Sonogashira route B Step 1 : 2-Chloro-4-phenylethvnyl-pyridine To the degassed mixture of triethylamine (375ml_) and acetonitrile (125ml_) was added 2-Chloro 4-iodopyridine (75g, 0.313mol), bis(triphenylphosphine) palladium(ll)chloride (4.4g, 2mol%) and copper iodide (0.6g, 1 mol%) sequentially. The mixture was stirred at room temperature for 3h. Phenylacetylene dissolved in acetonitrile(250 ml_) was then added dropwise to reaction mixture and it was stirred for 1 hr at room temperature. Reaction was monitored by TLC. Acetonitrile and triethylamine was removed under vacuo, and the residue was purified by column chromatography using silica with mixture of ethyl acetate and hexane solvent system to yield product (59g, 88%).1 H NMR (CDCIa): delta 8.36( d, J = 5.2 Hz, 1 H), 7.53-7.55 (m, 2H), 7.43( s, 1 H), 7.39- 7.42(m, 3H), 7.29(dd, J = 5.4 Hz, 1.2 Hz, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CEDERBAUM, Fredrik; UMARYE, Jayant; DUMEUNIER, Raphael; SONAWANE, Ravindra; WO2012/84678; (2012); 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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Formula: C5H3ClIN

Step 1 A round-bottomed flask was charged with 2-chloro-4-iodopyridine (600 mg, 2.5 mmol), thiophen-2-ylboronic acid (385 mg, 3.0 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (176 mg, 0.251 mmol), THF (9 mL) and 2M aqueous sodium carbonate (3.0 mL, 6.0 mmol). The reaction mixture was stirred at 70 C. overnight. The reaction mixture was cooled to room temperature then diluted with 20 mL water and extracted with 100 mL EtOAc (2*). The combined organic layers were washed with 20 mL water and 20 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on ~2 g SiO2 and chromatographed over 24 g SiO2 with EtOAc/hexanes (gradient: 0-10% EtOAc). All fractions containing product were combined and concentrated to give 430 mg (88%) of 2-chloro-4-thiophen-2-yl-pyridine as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem