Month: December 2020

Adding a certain compound to certain chemical reactions, such as: 5100-98-1, name is 3-Chloro-2-iodotoluene, 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 5100-98-1, Quality Control of 3-Chloro-2-iodotoluene

General procedure: A mixture of 17 (200 mg, 0.369 mmol), 2-bromo-1-methoxy-3-methylbenzene(148 mg, 0.737 mmol), Pd(OAc)2 (8.3 mg, 0.037 mmol), 2-dicyclohexylphosphino-2?,6?-di-isopropoxy-1,1?-biphenyl (34.4 mg,0.074 mmol), and Cs2CO3 (360 mg, 1.11 mmol) in toluene (7.5 ml) and water (1.5 ml) was stirred at 80 ¡ãC for 25 h. Then, water was added tothe reaction mixture, and the product was extracted with AcOEt. Theorganic layer was successively washed with water and brine, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue was purifiedby silica gel column chromatography (hexane/AcOEt=40/60 to 10/90) to give the title compound as a white solid (43 mg, 21percent).

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

Reference:
Article; Murafuji, Hidenobu; Sugawara, Hajime; Goto, Megumi; Oyama, Yoshiaki; Sakai, Hiroki; Imajo, Seiichi; Tomoo, Toshiyuki; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3639 – 3653;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), 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 627-31-6, category: iodides-buliding-blocks

(b) Synthesis of 1-(4-nitro-phenyl)-cyclobutanecarboxylic acid methyl ester (4-Nitro-phenyl)-acetic acid methyl ester (15.21 g, 76.9 mmol) was dissolved in anhydrous DMF (80 mL) and allowed to stir until all solid dissolved. The solution was cooled to 0 C. with an ice bath. Sodium hydride (6.32 g, 153.8 mmol; 60% dispersion in oil) was added slowly and cautiously. The resulting mixture was allowed to warm to about 20-35 C. and was stirred for approximately 15 min. The solution was cooled again to 0 C. with an ice bath. 1,3-Diiodopropane (17.7 mL, 153.8 mmol) was added slowly and drop-wise, and the resulting solution was allowed to stir at 0 C. for about 30 min. The solution was warmed to about 20-35 C. and stirred at about 20-35 C. for about 1 h. The solution was cooled to 0 C. with an ice bath and quenched with H2O, maintaining 0 C. throughout the quenching process. The reaction mixture was extracted 3 times with dichloromethane. The combined organic layers were washed with water and brine; dried over sodium sulfate; filtered; and then concentrated under vacuum to give product. The material was purified by column chromatography (SiO2, 80:20 hexane: EtOAc) and gave the title compound as a yellow solid material (7.5 g, 41% yield).1H NMR (300 MHz, CDCl3, TMS) delta 1.87-2.19 (m, 2H), 2.48-2.58 (m, 2H), 2.86-2.95 (m, 2H), 3.67 (s, 3H), 7.43 to 7.48 (m, 2H), 8.17-8.21 (m, 2H).LC-MSD (ES+): (m/z) 236 [(M+H)+, 100].

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; Dr. Reddy’s Laboratories Ltd.; US2010/144722; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, 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. HPLC of Formula: C8H6BrIO2

Methyl 500mL round bottom flask reactor, 5-bromo-2-iodo benzoate (20.0g, 59mmol), 4- dibenzofuran boronic acid (8.5g, 70 mol), tetrakis (triphenylphosphine) palladium (1.36 g, 0.12 mmol), potassium carbonate (16.2 g, 117.3mmol) and the mixture of toluene 100 mL, 110mL of tetrahydrofuran, the water was added 40 mL. The temperature of the reactor temperature was raised to 80 degrees and stirred overnight. When the reaction is finished the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate and the organic layer was separated. The organic layer was concentrated under reduced pressure and separated by column chromatography to give the intermediate 1-d. (15.0g, 67.1%)

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Co.,Ltd; PARK, SOK BAE; SONG, JU MAN; LEE, YU RIM; KIM, HEE DAE; PARK, SANG WOO; JONG, GYUNG SOK; CHA, SUN WOOK; (60 pag.)KR2015/128583; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 61272-76-2, name is 4-Fluoro-2-iodoaniline, molecular formula is C6H5FIN, 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. Recommanded Product: 4-Fluoro-2-iodoaniline

N-Benzyl-5-bromo-2-iodobenzamide (125 mg, 0.30 mmol), 4-fluoro-2-iodoaniline (29 pL, 0.25 mmol), copper(I) iodide (10 mg, 0.05 mmol), and potassium carbonate (86 mg, 0.63 mmol) were taken up in anhydrous DMSO (1.5 mL). The resulting reaction mixture was first stirred at 80 C for 2 hr, followed by heating to 135 C for another 10 hr. After cooling to room temperature, the mixture was diluted with an excess of Et2O and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : Hex = 0 : 100 to 100 : 0, EtOAc : DCM = 0 : 100 to 30 : 70) to give 10-benzyl-2-bromo-8-fluoro-5,10-dihydro-11H-dibenzo[5,e][1,4]diazepin-11-one (43 mg, 44 %) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta 8.06 (s, 1H), 7.74 (d, J = 2.4 Hz, 1H), 7.54 (dd, J =2.4, 85 Hz, 1H), 7.30 – 7.24 (m, 5H), 7.22 – 7.17 (m, 1H), 7.09 (dd, J = 6.0, 8.7 Hz, 1H), 7.04 (d, J= 8.9 Hz, 1H), 6.91 (td, J= 2.7, 8.4 Hz, 1H), 5.26 (s, 2H); LC/MS (ESI) m/z 396.73 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61272-76-2, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164932; (2019); 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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 5-bromo-2-iodobenzoate

Synthesis of Intermediate J-1 (0195) Quantities of 3 g (1 eq, 8.80 mmol) of methyl 5-bromo-2-iodobenzoate, 2.21 g (1.1 eq, 9.68 mmol) of dibenzo[b,d]thiophen-4-ylboronic acid, and 410 mg (0.04 eq, 0.35 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to a reaction chamber and vacuum dried, and the reaction chamber was filled with nitrogen gas. A quantity of 70 ml of toluene was added to the reaction chamber to dissolve the compounds, 30 ml of ethanol and 13 ml (3 eq, 26.4 mmol) of 2.0 M sodium carbonate aqueous solution were added to the reaction chamber to prepare a mixture, and the mixture was refluxed and agitated for 3 hours at a temperature of 120 C. Then, the mixture was washed with distilled water, and an organic layer was extracted using ethyl acetate. After drying the extracts using magnesium sulfate, the extracts were filtered, and the solvent was evaporated. Thereafter, 3.5 g of intermediate J-1 (methyl 5-bromo-2-(dibenzo[b,d]thiophen-4-yl)benzoate) (yield=75%) was obtained through column chromatography. (0196) 1H-NMR: 8.18 (m, 3H), 7.76 (t, 2H), 7.53 (t, 1H), 7.45 (m, 2H), 7.38 (d, 1H), 7.27 (d, 1H), 3.55 (s, 3H). APCI-MS (m/z): 397 [M+].

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; Samsung Display Co., Ltd.; Pusan National University Industry?University Cooperation Foundation; Kim, Soung-Wook; Kim, Myeong-Suk; Kim, Jae-Hong; Hwang, Jin-Soo; Suh, Hong-Suk; US8987462; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 135050-44-1, name is 3-Chloro-4-iodoaniline, 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 135050-44-1, Recommanded Product: 3-Chloro-4-iodoaniline

EXAMPLE 8 (METHOD 2A) (3-Chloro-4iodo-phenyl)-carbamic acid tert-butyl ester To a solution of 3-chloro-4-iodo-aniline (10 g) in tetrahydrofuran (40 mL) containing diiso-propylethylamine (6.9 mL) is added di-tert-butyl-dicarbonate (8.6 g) and the mixture is heated to reflux. After approximately 15 hours additional portions of diisopropylethylamine (6.9 mL) and di-tert-butyl-dicarbonate (21 g) is added and heating is continued for approximately 24 hours. The solution is then cooled, concentrated under reduced pressure, diluted with ethyl acetate, and washed successively three times with 5% aqueous hydrochloric acid then once with saturated aqueous sodium chloride. The solution is dried over anhydrous sodium sulfate then concentrated under reduced pressure to provide the desired crude product as a brown oil. Crystallization is induced by addition of hexanes, and the collected solid material is recrystallized from hexanes to give the desired product as a white solid.

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; American Home Products Corporation; US6166028; (2000); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 4028-63-1,Some common heterocyclic compound, 4028-63-1, name is 2,4,6-Trimethyliodobenzene, molecular formula is C9H11I, 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.

The cuprous iodide (24 mg, 0.12mmol) and tetrakis(triphenylphosphine)palladium (43 mg, 0.06 mmol) were loadedinto a Teflon-sealed flask. 2-iodo-1,3,5-trimethylbenzene (0.51 g, 2.08 mmol) andphenylacetylene (0.26 g, 2.5 mmol) were loaded into a separate flask and dissolved intriethylamine (40 mL). This solution was then cannula-transferred into the flaskcontaining the catalysts, the solution was briefly degassed under vacuum, and theflask was sealed. The mixture was stirred under nitrogen at 80 ¡ãC for 6 h. The crudeproduct was purified by column chromatography (SiO2, eluent: petroleum ether) togive 2g as a colorless liquid in 92.0percent yield. (0.42 g, 1.91 mmol). 1H NMR (300 MHz,CDCl3): 7.51-7.54 (m, 2H), 7.33 (d, J = 7.1 Hz, 3H), 6.88 (s, 2H), 2.47 (s, 6H), 2.28(s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6-Trimethyliodobenzene, its application will become more common.

Reference:
Article; An, Wenbo; Li, Gaoqiang; Ma, Jun; Tian, Youping; Xu, Feng; Synlett; vol. 25; 11; (2014); p. 1585 – 1590;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 18698-96-9 as follows. Computed Properties of C8H7IO2

A suspension of 2-iodophenyl acetic acid (1 g, 3.82 mmol), 4-bromobenzenethiol (0.722 g, 3.82 mmol), KOH (0.427 g, 7.63 mmol) and copper powder (24 mg, 0.38 mmol) in 2 mL of water, was allowed to react in microwave (conditions: 2.x.6 min, 180 W, T max=100¡ã C., P max=100 psi). The suspension obtained was dissolved in 2N aqueous solution of KOH and then filtered. The filtrate was acidified with 1N aq. HCl; the white precipitate was filtered, dried in vacuo, purified by trituration with acetone to give the pure acid 1-bis as white solid (1.16 g, 94percent).1H-NMR (CDCl3, 200 MHz): 7.44 (d, J=7 Hz, 1H); 7.36-7.26 (m, 5H); 7.01 (d, J=8.4 Hz, 2H); 3.86 (s, 2H).Anal. Calcd. for C14H11BrO2S (MW=323.2): C, 52.03; H, 3.43; Br, 24.72; O, 9.90; S, 9.92.

According to the analysis of related databases, 18698-96-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRACCO IMAGING SPA; US2009/239829; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 1173707-01-1, name is N-(5-Fluoro-2-iodophenyl)acetamide, molecular formula is C8H7FINO, 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: C8H7FINO

General procedure: N-(2-iodophenyl)acetamide (100.0 mg, 0.38 mmol, 1.0 equiv) in CH3CN (5.0 mL) was added sequentially with PdCl2(PPh3)2 (5.4 mg, 0.01 mmol, 0.02 equiv), Ph3P (4.0 mg, 0.02 mmol, 0.04equiv), 1-chloro-4-ethynylbenzene (57.6 mg, 0.42 mmol, 1.1 equiv). The resulting solution was degassed by passing through a steady stream of argon for 30 min (flask 1). In the meantime in another flask, a mixture of CuI (3.0 mg, 0.02 mmol, 0.04 equiv) in Et3N was also degassed bypassing through a steady stream of argon for 30 min (flask 2). After degassing, the mixture ofCuI in Et3N in flask 2 was transferred into the solution in flask 1 using a syringe with wide-boarneedle which resulted in the reaction solution turning yellow and giving white precipitates. The reaction mixture was allowed to stir at room temperature overnight and was quenched byaddition with sat. aq. NH4Cl. The separated aqueous phase was extracted with EtOAc (3x times).The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30-50% EtOAc-hexane to yield 114.6 mg of compound 1d (>99%)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 1173707-01-1, its application will become more common.

Reference:
Article; Chaisan, Nattawadee; Kaewsri, Wilailak; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Ruchirawat, Somsak; Tetrahedron Letters; (2018); p. 675 – 680;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

156150-67-3, name is 2-Chloro-1-fluoro-4-iodobenzene, 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. Product Details of 156150-67-3

To a 50 ml of isopropyl alcohol solution containing 15.0 g of 3 (S) -aminopyrrolidine-1-carboxylic acid tert-butyl ester (80.5 mmol) and 24.8 g of 2-chloro-l-fluoro-4-iodobenzene(96.7 mmol) were added 1.54 g of copper (I) iodide (8.1 mmol),9.0 ml of ethylene glycol (10.1 mmol) and 34.2 g of potassium phosphate (161 mmol) , and heated under reflux under a nitrogen atmosphere for 46 hours. The reaction solution was cooled to room temperature and filtered using Celite. The substance remained in the filter was washed with ethyl acetate and the filtrate was concentrated under reduced pressure together with the washings, and the residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 4 : 1) . The solvent was distilled off under reduced pressure, and the residue was recrystallized from diethyl ether to thereby obtain 15.9 g of white powdery 3 (S)- (3- chloro-4-fluorophenylamino)pyrrolidine-l-carboxylic acid tert- butyl ester. 1H-NMR(CDCl3) deltappm: 1.47(9H,s), 1.78-1.96 (lH,m) , 2.10-2.28 (IH,m) , 2.10-2.28 (lH,m) , EPO 3.11-3.30 (IH,m), 3.30-3.56 (2H,m) , 3.57-3.79 (2H,m) , 3.85- 4.03(lH,m), 6.38-6.47 (IH,m) , 6.60 (IH, dd, J=6. OHz, J=2.9Hz) , 6.90- 7.00 (IH,m) .

The synthetic route of 156150-67-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2006/121218; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com