Category: iodides-buliding-blocks

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. 54811-38-0, name is 5-Iodo-2-methylbenzoic acid, A new synthetic method of this compound is introduced below., 54811-38-0

A solution of 5-iodo-2-methylbenzoic acid (50.0 g, 190.0 mmol) in thionyl chloride (250 mL) was heated at reflux for 3 hours. The completion of reaction was observed by TLC (by converting acid chloride to methyl ester). The thionyl chloride was evaporated and the residue was charged to the reaction mixture contained 2-amino pyridine (19.72 g, 209.8 mmol), triethyl amine (82.75 mL, 572.5mmol) in dry ethyl acetate (500 mL) at 0C. The reaction mixture was stirred at RT(room temperature) for 12 hours. The completion of reaction was observed byTLC. The reaction mixture was taken in water (2000 mL), extracted with ethylacetate (2 x 1000 mL). The combined organic layer was washed with water (2 x1000 mL), brine, dried over sodium sulphate and evaporated. The crude material was purified by column chromatography using ethyl acetate in petroleum ether to afford 5-iodo-2-methyl-N-(pyridin-2-yl)benzamide intermediate 6 (30.0 g, 48 %) as pale yellow solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SANOFI; PASCAL, Cecile; PELLET, Alain; COURTEMANCHE, Gilles; CAMPBELL, Simon; (78 pag.)WO2019/8027; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 455-13-0, name is 4-Iodobenzotrifluoride, 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 455-13-0. 455-13-0

General procedure: In a 10 mL glass tube was placed 4-iodotoluene (219 mg, 1 mmol), potassium thiocyanate (243 mg, 2.5 mmol), copper(I) oxide (43 mg, 0.3 mmol), tetrabutylammonium bromide (97 mg, 0.3 mmol), and water (1 mL). The mixture was stirred for 1 min before sealing the tube with a septum and placing the reaction mixture into the microwave cavity (CEM Discover). An initial microwave power of 150 W was used, the temperature being ramped from rt to 200 C where it was held for 60 min (caution: The water is heated well above its boiling point so all necessary precautions should be taken when performing such experiments. Vessels designed to withhold elevated pressures must be used. The microwave apparatus used here incorporates a protective metal cage around the microwave vessel in case of explosion. After completion of an experiment, the vessel must be allowed to cool to a temperature below the boiling point of the solvent before removal from the microwave cavity and opening to the atmosphere.). The reaction mixture was stirred continuously throughout. The reaction was run in triplicate. After allowing the three identical reaction mixtures to cool to rt, the vessels were opened and their contents poured into a separatory funnel and the tubes washed three times with ethyl acetate (approximately 3 mL each time) followed by two washes with water (5 mL each time). All washings were added to the separatory funnel along with an additional 20 mL of ethyl acetate. Typically an emulsion was formed after shaking; therefore brine (approximately 5 mL) was added to aid separation. The aqueous layer was extracted twice more with ethyl acetate (approximately 30 mL each time). The organic washings were combined, washed with deionized water (approximately 20 mL), collected, dried over MgSO4, and then the ethyl acetate removed in vacuo. Purification was accomplished by column chromatography (100% hexanes) affording the product as a white solid (152 mg, 48%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-Iodobenzotrifluoride.

Reference:
Article; Kelly, Christopher B.; Lee, Christopher Xiang; Leadbeater, Nicholas E.; Tetrahedron Letters; vol. 52; 36; (2011); p. 4587 – 4589;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

766-85-8, Adding some certain compound to certain chemical reactions, such as: 766-85-8, name is 3-iodoanisole, 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 766-85-8.

i) l-Bromo-2-iodo-4-methoxy-benzene Bromine (2.8 mL, 54.49 mmol) was added dropwise over 5 minutes to a solution of 3- iodoanisole (10.01 g, 42.77 mmol) in glacial acetic acid (65 mL). The resulting orange solution was stirred at room temperature for 24 hours. The reaction mixture was diluted with water and extracted with hexane. The combined extracts were washed with aqueous sodium thiosulfate solution (5%) and brine, dried over magnesium sulfate and concentrated under reduced pressure to give 13.51 g (quantitative yield) of the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 7.47 (d, 1 H) 7.39 (d, 1 H) 6.77 (dd, 1 H) 3.77 (s, 3 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 766-85-8.

Reference:
Patent; ASTRAZENECA AB; BYLUND, Johan; EK, Maria, E; HOLENZ, Joerg; KERS, Annika; OeHBERG, Liselotte; WO2010/132016; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

13421-00-6, name is 5-Chloro-2-iodobenzoic acid, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 13421-00-6

To a solution of 5-chloro-2-iodobenzoic acid (3.0 g, 10.6 mmol) in toluene (150 mL), SOCl2 (7.75 mL, 106 mmol) was added and the mixture was heated at 100 C. for 3 hours. The solvent was concentrated in vacuum and the residue was co-evaporated from toluene twice to give the title compound as a grey solid. Yield (3.2 g, 100%) [0177] 1H NMR (400 MHz, CDCl3): delta 7.26 (dd, 1H), 7.98 (d, 1H), 8.03 (d, 1H).

Statistics shows that 13421-00-6 is playing an increasingly important role. we look forward to future research findings about 5-Chloro-2-iodobenzoic acid.

Reference:
Patent; Stasi, Luigi Piero; Rovati, Lucio Claudio; US2015/65523; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 31599-61-8

General procedure: Under an ambient atmosphere, Pd(PPh3)4 (116 mg, 5 mol%), K2CO3 (552 mg, 4.0 mmol), and the corresponding aryl iodide (2.0 mmol) were suspended in MeOH (5 mL) and toluene (5 mL) in a 25 mL flask. Dimethyl (1-diazo-2-oxopropyl)phosphonate (499 mg, 1.3 equiv) was then added, and the resulting solution was stirred at r.t. for 5 h. The mixture was filtered through a short pad of silica gel eluting with EtOAc and the filtrate was evaporated in vacuo to remove the volatile materials. The crude residue was purified by column chromatography (silica gel, EtOAc-PE, 1:1) to afford the respective final product 3; yield: 50-90%.

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, 31599-61-8, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Chenggui; Ye, Fei; Wu, Guojiao; Xu, Shuai; Deng, Guisheng; Zhang, Yan; Wang, Jianbo; Synthesis; vol. 48; 5; (2016); p. 751 – 760;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 191348-14-8 name is 2-Iodo-4-methoxyaniline, This 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. 191348-14-8

General procedure: General procedure for the synthesis of N-Boc Indoles: (Step 1) A mixture of o-iodoaniline (10 mmol), CuI (19.5 mg, 0.1 mmol, 1.0 mol%) and Pd(PPh3)2Cl2 (140.4 mg, 0.2 mmol, 2.0 mol%) in dry NEt3 (20 mL) was added into a three-neck flask (50 mL) and stirred at room temperature in nitrogen atmosphere. Followed by dropwise addition of alkyne (12.0 mmol, 1.2 equiv) and the mixture was stirred at room temperature (rt) until complete disappearance of the o-iodoaniline (TLC monitoring). Then saturated NH4Cl solution was added and the mixture was stirred for another 30 minutes. The mixture was extracted with dichloromethane (30 mL¡Á3) and the organic layer was washed with brine solution, dried over anhydrous Na2SO4, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography. (Step 2) The purified product of Step 1 and PdCl2 (5.0 mol%) in CH3CN (25 mL) was heated at 85 C in a round-bottom (50 mL) under nitrogen atmosphere until complete disappearance of the starting material (TLC monitoring). The mixture was allowed reach to rt, the solvent was evaporated under reduced pressure and the residue was purified with by column chromatography. (Step 3) The product of Step 2 and (Boc)2O (1.1 equiv) in dry CH3CN (20 mL) was (50 mL) was stirred at room temperature in a round-bottom (50 mL). Then 4-(N,N-dimethylamino)pyridine (3.0 mol%) was added and the mixture was stirred at room temperature until complete disappearance of the starting material (TLC monitoring). Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography.

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

Reference:
Article; Zhou, Xiao-Yu; Chen, Xia; Wang, Liang-Guang; Yang, Dan; Li, Zhi; Synthesis; vol. 49; 16; (2017); p. 3662 – 3669;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

51560-21-5, The chemical industry reduces the impact on the environment during synthesis 51560-21-5, name is 1,4-Diiodo-2,5-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

In a 100.0mL Schlenk flask equipped with astir bar, 10 (0.2500 g, 0.641mmol), PdCl2(PPh3)2 (0.0442 g, 0.0632mmol), and CuI (0.3762 g, 1.976mmol) were added. A condenser was added, and the apparatus was purged andfilled with argon. Through the sidearm of the flask, 5.0mL of distilled triethylamine and 10.0mL of distilled toluene were added via a purged and filled airtight syringe. Lastly, 15mLof TMS acetylene was placed in a small round bottom flask and was degassed with argon for about 10 min before it was added through the sidearm of the Schlenk flask (0.1916 mL,1.346mmol) with a purged and filled airtight syringe. The apparatus was lowered into an 80C oil bath and heated for 24 hours. The solvent was removed from the light orange reaction mixture via rotary evaporation, and the solid was extracted with 10 mL of ethyl acetate and 10 minutes o fsonication. The remaining solid was removed via filtration,and the filtrate was rotovapped to produce crude product 11as a grayish/gold solid. The product was purified via MPLC on silica. The product eluted at 70 : 30 hexanes : ethyl acetate in quantitative yield. 1H NMR (500MHz, CDCl3) delta 0.21 (s,CH3, 18H), 3.76 (s, OCH3, 6H), 6.86 (s, Ph, 2H).

The chemical industry reduces the impact on the environment during synthesis 1,4-Diiodo-2,5-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Basinger, Corinne A.; Sullivan, Kaitlin; Siemer, Sarah; Oehrle, Stuart; Walters, Keith A.; Journal of Chemistry; vol. 2015; (2015);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

117832-17-4, Adding some certain compound to certain chemical reactions, such as: 117832-17-4, name is 2-Iodo-4,5-dimethylaniline, 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 117832-17-4.

General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 muL, 0.5 mmol) 2a, (DMEDA) (3 muL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 117832-17-4.

Reference:
Article; Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua; Synlett; vol. 24; 17; (2013); p. 2315 – 2319;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

20776-54-9, Name is 2-Amino-4-iodobenzoic acid, 20776-54-9, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

[00313] Step A: To a solution of 2-amino-4-iodobenzoic acid (2.5 g, 9.50 mmol) in DMF (10 mL) at rt under argon were added EDCI (2.18 g, 11.40 mmol), 1 – hydroxybenzotriazole (1.54 g, 11.40 mmol), DIEA (1.98 mL, 11.40 mmol), and ammonia (7.0 N solution in MeOH; 1.90 mL, 13.30 mmol). The dark solution was stirred at rt overnight and diluted with H2O until precipitate formed. The precipitate was separated by filtration, washed with H2O, and dried under high vacuum for several hours to afford 2-amino-4-iodobenzamide as a tan solid (1.3 g, 52%). LC-MS (ESI) m/z 263 (M + H)+.

Statistics shows that 2-Amino-4-iodobenzoic acid is playing an increasingly important role. we look forward to future research findings about 20776-54-9.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6828-35-9, 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. 6828-35-9, name is 5-Chloro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 5-chloro-2-iodoaniline (18.7 g, 0.074 mol, 1.0 eq.) in 500 mL of water was added hydroxylamine hydrochloride (18.5 g, 0.27 mol, 3.6 eq.), sodium sulfate (84.0 g, 0.59 mol, 8.0 eq.), chloral hydrate (14.7 g, 0.89 mol, 1.2 eq.) and 2N aqueous hydrochloric acid (25 mL). The mixture was stirred at 70 C for 18 h, then allowed to cool to room temperature. The resulting mixture was extracted with EtOAc (400 mL X 3) and the combined organic layers were dried (Na2S04), filtered and concentrated to afford compound 2 (17.0 g, 72.1% yield).

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.

Reference:
Patent; LUDWIG INSTITUTE FOR CANCER RESEARCH LTD; GAHMAN, Timothy; SHIAU, Andrew; KOLODNER, Richard; (234 pag.)WO2017/51251; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com