Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, belongs to iodides-buliding-blocks compound, 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 460-37-7, category: iodides-buliding-blocks

Example 40/V-{[(2S)-5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1 ,4-BENZODIOXIN-2- YL]METHYLJ-N-(S1S1S-TRIFLUOROPROPYL)AMINEA mixture of 1 -[(2S)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1 ,4-benzodioxin-2- 5 yl]methaneamine (0.3 g, 1.1 mmol), 1 ,1 ,1 -trifluoro-3-iodopropane (0.16 ml, 1.4 mmol) K2CO3 (0.32 g, 2.3 mmol) and ACN (4 ml) was heated under microwave radiation at 1200C for 30 min. The mixture was filtrated and evaporated to dryness and the product was purified by flash column chromatography (EtOAc).Yield: 0.12 g, 31 %. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M. p. 10 233C. MS m/z (rel. intensity, 70 eV) 357 (M+, 1 ), 274 (3), 127 (5), 126 (bp), 69 (3). [alpha]= -53 (MeOH).

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; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; WO2009/133107; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 21304-38-1, 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. 21304-38-1 name is 4-Iodobenzene-1,2-diamine, 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.

To a solution of 4-iodo-l,2-phenylenediamine (0.47 g) in dichloromethane (3 ml) 3-(2- bromophenyl)glutaric anhydride (0.54 g) was added with stirring at rt. Almost instantaniously an resinous precipitate is formed. After 1 h at rt the solvent was removed by decantation and the residue dried in vacuo to give an amorphous solid (0.52 g). The solid is dissolved in 1,4-dioxane (1 ml) and 4M HCI in 1,4-dioxane (3 ml) is added. The resulting dark solution is heated to reflux for 1 h whereupon a precipitate is formed. After cooling to rt the precipitate is collected by suction filtration, washed with 1,4-dioxane and diethyl ether, and dried in vacuo to give 3- (2-bromophenyl)-4-(5-iodo-2-benzimidazolyl)butanoic acid HCI (0.27g) as light grey solid.1H-NMR (500 MHz, DMSOd6)): delta (ppm) = 2.81 (dd, J = 16.4, 7.4 Hz, IH), 2.88 (dd, J = 16.6, 7.0 Hz, IH), 3.44 (dd, J = 14.5, 8.4 Hz, IH), 3.54 (dd, J = 14.6, 7.0 Hz, IH), 4.16 (m, IH), 7.14 (dt, J = 7.8, 1.6 Hz, IH), 7.37 (dt, J = 7.7, 1.1 Hz, IH), 7.51 (dd, J = 8.0, 1.2 Hz, IH), 7.54 (m, 2H), 7.75 (dd, J = 8.6, 1.5 Hz, IH), 8.08 (d, J = 1.3 Hz, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 31.60 (CH2), 38.67 (CH2), 39.01 (CH), 89.46 (C), 115.75 (CH), 122.07 (CH), 123.60 (C), 128.20 (CH), 128.34 (br, CH), 128.89 (CH), 130.78 (C), 132.71 (CH), 132.86 (br, C), 133.67 (CH), 140.36 (C), 152.04 (C), 171.97 (CO).

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

Reference:
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

General procedure: To a screw-capped vial (50 ml) were added aryl iodides 1(1.0 mmol), benzonitrile 2a (155 mg, 1.5 mmol), K2CO3 (276 mg,2.0 mmol), NaOH (40 mg,1.0 mmol), CuI (19 mg, 0.1 mmol), DMEDA(9 mg, 0.1 mmol), and [bmim]PF6 (14 mg, 0.05 mmol) in water(2 ml). The vial was flushed with nitrogen then sealed with the cap,and allowed to stir at 100 C for the specific reaction time. Thereaction mixture was extracted with EtOAc (315 ml). The combined organic extracts were dried over Na2SO4 for 12 h andevaporated under vacuum. The crude products were purified ina silica gel column for further purification, using PE/EtOAc (5:1) asthe eluent.

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:
Article; Wang, Jichao; Yin, Xinchi; Wu, Jun; Wu, Datong; Pan, Yuanjiang; Tetrahedron; vol. 69; 48; (2013); p. 10463 – 10469;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 6828-35-9, 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 6828-35-9 as follows.

1 mmol of 5-chloro-2-iodoaniline, 3 mL of aqueous ammonia at a concentration of 12 mol / L was added to the reaction vessel, 4-methylbenzaldehyde mmol, 0.1 mmol of copper chloride, 0.1 mmol of proline lithium, 1 mmol of sodium hydroxide, 3 mL of water and 1 mL of water. Placed in a microwave reactor at 150 w of power heated to 100 C for 15 min continuous reaction. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The product was purified by column chromatography to give a white solid in 84% yield.

According to the analysis of related databases, 6828-35-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujian Medical University; Ke Fang; Zhang Peng; Xu Jianhua; Wu Wen; Zheng Yu; Wu Lixian; (9 pag.)CN106866543; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 191348-14-8, name is 2-Iodo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-4-methoxyaniline

Step D: Preparation of Ethyl 2-(7-Hydroxy-l,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)acetate.2-Iodo-4-methoxyaniline (2.0 g, 8.03 mmol) and ethyl 2-(2-oxocyclopentyl)acetate (2.05 g, 12.1 mmol) were dissolved in DMF (30 mL) and tetraethyl orthosilicate (2.12 g, 10.4 mmol) and pyridinum /7-toluenesulfonate (PPTS) (0.081 g, 0.321 mmol) were added. The reaction mixture was heated and stirred at 135 C for 4 h. After cooling to 120 C, DIEA (3.11 g, 24.09 mmol) and palladium (II) acetate (0.054 g, 0.241 mmol) were added. The reaction mixture was stirred for 3 h and then partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resultant solution was diluted with 50% ethyl acetate in hexanes and filtered through a pad of silica gel. The filtrate was concentrated and purified by silica gel column chromatography to give 1.9 g of ethyl 2-(7-methoxy-l,2,3,4- tetrahydrocyclopenta[b]indol-3-yl)acetate containing residual ethyl 2-(2-oxocyclopentyl)acetate. The mixture was dissolved in DCM (80 mL) and cooled to 0 C. Boron tribromide (21.0 mL, 21.0 mmol, 1.0 M in DCM) was added and the reaction was stirred for 1.5 h. Ice water was added and the reaction mixture was allowed to reach room temperature. The aqueous mixture was extracted three times with DCM. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (650 mg). LCMS m/z = 260.3 [M+H]+; NMR (400 MHz, CDC13) delta ppm 1.29 (t, J = 7.2 Hz, 3 H), 2.05-2.14 (m, 1H), 2.50 (dd, J= 16.8, 11.2 Hz, 1H), 2.68-2.86 (m, 4H), 3.48-3.58 (m, 1H), 4.16-4.24 (m, 2H), 6.66 (dd, J = 8.6, 2.4 Hz, 1H), 6.85 (d, J= 2.4 Hz, 1H), 7.15 (d, J= 8.7 Hz, 1H), 8.4 (s, 1H).

According to the analysis of related databases, 191348-14-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; MONTALBAN, Antonio, Garrido; BUZARD, Daniel, John; DeMattei, John, Aldo; GHARBAOUI, Tawfik; JOHANNSEN, Stephen, Robert; KRISHNAN, Ashwin, M.; KUHLMAN, Young, Mi; MA, You-An; MARTINELLI, Michael, John; SATO, Suzanne, Michiko; SENGUPTA, Dipanjan; WO2011/94008; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, 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. COA of Formula: C8H7IO

General procedure: 2-Trimethylsilylpyridine (1.2mmol), the aryl halide (1mmol), palladium acetate (0.10mmol), CataXCium A (0.2mmol), CuI (76mg, 0.4mmol) and KF (2.20mmol) were combined in reaction tubes in a Radleys green-house parallel synthesiser under a flow of nitrogen and degassed DMF (1ml) was added. The resulting suspensions were stirred at 90 oC under nitrogen for 12 hours. Reactions were analysed by LC-MS at 1mg/1ml in methanol to determine the yield.

The synthetic route of 1-(3-Iodophenyl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Blakemore, David C.; Marples, Louise A.; Tetrahedron Letters; vol. 52; 32; (2011); p. 4192 – 4195;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 2142-70-3, name is 1-(2-Iodophenyl)ethanone, molecular formula is C8H7IO, 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. Quality Control of 1-(2-Iodophenyl)ethanone

The operation method of the specific synthesis is the same as that in Example 1, specifically: 1-(2-iodobenzene) ethyl-1-one (1 mmol) and 50 mL of trifluorotoluene are added to the flask,Stir to dissolve 1-(2-iodobenzene) ethyl-1-one in trifluorotoluene, then add 2N HCl (0.5mL),Then, sodium dichromate (0.30g) was added under acidic conditions, heated to 95C and reacted under reflux at this temperature for 6h.After the reaction, spin off the trifluorotoluene in the system, add sodium hydroxide to the water phase to adjust the water phase to pH 9 to remove impurities, and then add hydrochloric acid to the water phase to adjust the water phase to pH 3,After extraction and recrystallization from petroleum ether, the product 2-(2-iodobenzene)-2-glyoxylic acid was obtained with a yield of 86%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2142-70-3, its application will become more common.

Reference:
Patent; Suzhou Aimate Biological Technology Co., Ltd.; Wang Mingzhong; Zhu Mingxin; Su Dao; Li Jinjin; (13 pag.)CN111116358; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 624-76-0, The chemical industry reduces the impact on the environment during synthesis 624-76-0, name is 2-Iodoethanol, I believe this compound will play a more active role in future production and life.

N-methylaniline (5 mls, 0.05 mol) was reacted with 2-Iodoethanol (3.599 mls, 0.05 mol) and diisopropylethylamine (8.039 mls, 0.05 mol) in ACN at 70 C. for 16 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc to provide the compound as a yellow orange oil, 2a (4.48 g, 0.03 mol, 64.5% yield). 1H NMR (400 MHz, Chloroform-d) delta 7.27-7.15 (m, 2H), 6.81-6.67 (m, 3H), 3.74 (t, J=5.8 Hz, 2H), 3.42 (t, J=5.8 Hz, 2H), 2.92 (s, 3H).

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, 2-Iodoethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CINCINNATI CHILDREN’S HOSPITAL MEDICAL CENTER; UNIVERSITY OF CINCINNATI; Merino, Edward J.; Mulloy, James C.; Li, Guorui; Bell-Horwath, Tiffany; US2013/230542; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 51628-12-7, 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 51628-12-7 as follows.

General procedure: A stirred mixture of 4-iodophenylacetonitrile (35), arylboronic acid (36-45) (1.1 equiv), Pd(PPh3)4 (0.03 equiv), KBr (1.1 equiv), and K3PO4 (2.5 equiv) in dioxane (5 mL/mmol) was purged with N2 for10 min at room temperature and then stirred overnight at 85 C under N2. The mixture was diluted with water and extracted with AcOEt. The organic phase was washed three times with water, dried (Na2SO4), and evaporated under vacuum. The residue was chromatographedon silica gel.

According to the analysis of related databases, 51628-12-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ortar, Giorgio; Morera, Enrico; De Petrocellis, Luciano; Ligresti, Alessia; Schiano Moriello, Aniello; Morera, Ludovica; Nalli, Marianna; Ragno, Rino; Pirolli, Adele; Di Marzo, Vincenzo; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 118 – 132;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 216393-67-8, 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. 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Chloro-2-fluoro-6-iodoaniline (0.100 g; 0.368 mmol), 4-(3-fluorobenzyl)-N-(4-(triethylsilyl)but-3-ynyl)benzamide (0.145 g; 0.368 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.015 g; 0.018 mmol), lithium chloride (0.016 mg; 0.368 mmol) and sodium carbonate (0.078 g; 0.737 mmol) were suspended in DMF (5 mL) and the mixture was stirred at 100 C. for 18 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane) to afford 0.102 g (51%) of the title compound as a yellow oil. [0672] ESI/APCI(+): 539 (M+H).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-fluoro-6-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Griffioen, Gerard; Van Dooren, Tom; Rojas De La Parra, Veronica; Allasia, Sara; Marchand, Arnaud; Kilonda, Amuri; Chaltin, Patrick; US2013/274260; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com