Month: July 2021

Synthetic Route of 82998-57-0,Some common heterocyclic compound, 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, molecular formula is C8H7IO2, 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 3-iodo-4-methyl-benzoic acid (10.0 g, 38.2 mmol) in methanol (70 ml) is added concentrated sulfuric acid (0.5 ml). The reaction mixture is heated at 70C for 48 hours, cooled to room ambient temperature and then concentrated. After that, ethyl acetate (100 ml) and aqueous NaHCO3 (saturated, 100 ml) solution are added to the residue. The organic layer is separated and washed again with aqueous NaHCO3 (saturated, 100 ml) solution. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to yield 3-iodo-4-methyl-benzoic acid methyl ester 1. It is used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1 H), 7.87 (d, 1 H, J = 8.4 Hz), 7.48 (d, 1 H, J = 8.4 Hz), 3.85 (s, 3 H), 3.35 (s, 3H); LC-MS m/z: 277.0 (M+1).

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; DIERKS, Christine; WARMUTH, Markus; WU, Xu; (20 pag.)EP2162190; (2016); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 181765-85-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 181765-85-5, name is Methyl 4-chloro-2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: reaction vial (8 ml) was charged with benzoazine (0.10 mmol, 1.0 equiv.), template-MeCN (0.10 mmol, 1.0 equiv.) and 0.2 ml dichloromethane. The mixture was stirred for 5 min at room temperature, and then concentrated in vacuo. Pd(OAc)2 (2.2 mg,10 mumol, 10 mol%), Ac-Gly-OH (2.3 mg, 20 mumol, 20 mol%), aryl iodide (0.3 mmol,3 equiv.), AgOAc (50 mg, 0.30 mmol, 3.0 equiv.), Ag2CO3 (27.6 mg, 0.1 mmol,1.0 equiv.), NBE-CO2Me (22.8 mg, 0.15 mmol, 1.5 equiv.) and HFIP (1.5 ml) were added. The reaction vial was sealed and allowed to stir at 80 C for 18 h. The reaction mixture was cooled to room temperature. Then a solution of DMAP (36.7 mg, 0.3 mmol, 3 equiv.) in toluene (1.5 ml) was added. The mixture was stirred at 80 C for 15 min. The reaction mixture was cooled to room temperatureand diluted with EtOAc. The mixture was filtered through a short pad of celite and eluted with EtOAc (2 × 2 ml). The filtrate was evaporated under reduced pressure. (If the product release was not complete, a solution of DMAP (18.4 mg,0.15 mmol, 1.5 equiv.) in toluene (1.5 ml) was added; the solution was then stirredat 80 C for 15 min and then concentrated.) Purification by preparative thin-layer chromatography afforded the title compound

The synthetic route of Methyl 4-chloro-2-iodobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bay, Katherine L.; Chen, Xiangyang; Houk, Kendall N.; Lu, Yi; Shi, Hang; Tanaka, Keita; Verma, Pritha; Weng, Jiang; Yu, Jin-Quan; Nature Chemistry; (2020);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 103962-05-6

The triazole (70 mg, 0.41 mmol), l-iodo-4-trifluoromethoxybenzene (142 mg, 0.493 mmol), Cs2CO3 (535 mg, 1.644 mmol), CuI (3 mg, 0.012 mmol), 8-hydroxyquinoline (2 mg, 0.012 mmol), and DMF/Eta2O (2 mL; 10:1 solution) were combined in a 10 mL CEM Microwave reaction vessel fitted with magnetic stir bar and subjected to microwave irradiation at 150 0C for 30 min. The contents were then filtered and concentrated to dryness affording the 1,3- diphenyl triazole intermediate (18 mg, 13percent).

The synthetic route of 103962-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; BROWN, Annette; CROUSE, Gary; SPARKS, Thomas; MCLEOD, CaSandra; RIGSBEE, Emily; LAMBERT, William; NIYAZ, Noormohamed; WO2011/17504; (2011); A1;,
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. 72373-82-1, name is 1-Chloro-2-fluoro-3-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H3ClFI

[00343] Intermediate 13A. Ethyl l-(3-chloro-2-fluorophenyl)-lH-imidazole-4- carboxylate, 1 TFA: A mixture of l-chloro-2-fluoro-3-iodobenzene (0.549 g, 2.141 mmol), ethyl lH-imidazole-4-carboxylate (0.3 g, 2.141 mmol), copper(I) iodide (0.082 g, 0.428 mmol), L-proline (0.099 g, 0.856 mmol), and K2C03 (0.888 g, 6.42 mmol) in DMSO (4.28 mL) was vacuumed and back-filled with argon for three times, then capped and heated at 110 °C. After 20 h, the reaction mixture was cooled to rt and diluted with EtOAc. The organic layer was washed with H20, brine, dried over Na2S04, filtered, and concentrated. The crude product was then purified using reverse phase HPLC chromatography to yield the desired product (0.01 g, 1.2percent) as a colorless oil. MS(ESI) m/z: 269.0 (M+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 72373-82-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 340825-13-0, 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 340825-13-0 as follows.

Alternative Procedure: A solution of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (5.0 g, 18.4 mmol), 4-fluorobenzenethiol (4.1 mL, 38.6 mmol) and absolute ethanol (20 mL) was cooled on an ice-water bath and bubbled with HCl gas until saturation was reached (observed by the formation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in diethyl ether (250 mL) and washed sequentially with water (2*125 mL), 0.5 M aqueous Na2CO3 (3*100 mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.20 g) which was a mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane). The solid was dissolved in chloroform (150 mL) and cooled in an ice-water bath. A solution of mCPBA (35.0 g, 156 mmol) in DCM (200 mL) was washed with brine (50 mL), dried over Na2SO4, filtered, and the filter cake was washed with DCM (50 mL). The combined filtrates were added dropwise in portions to the chloroform solution of the mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) until the reaction was completed as judged by LCMS (175 mL of the mCPBA solution was needed). The mixture was cooled in an ice bath, filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueous Na2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2*120 mL), 10% aqueous Na2CO3 (3*200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4-fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white amorphous solid.

According to the analysis of related databases, 340825-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Marcoux, David; Beaudoin Bertrand, Myra; Dhar, T.G. Murali; Yang, Michael G.; Xiao, Zili; Xiao, Hai-Yun; Zhu, Yeheng; Weigelt, Carolyn A.; Batt, Douglas G; (154 pag.)US2018/127368; (2018); 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. 59528-27-7, name is (4-Iodophenyl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., COA of Formula: C7H9ClIN

A mixture of (4-iodophenyl)methanamine hydrochloride (2.64 g, 9.80 mmol, 1.0 eq), (lS,2S)- Nl,N2- dimethylcyclohexane-l, 2-diamine (0.31 mL 1.96 mmol, 0.2 eq), Sodium ascorbate (198 mg, 0.98 mmol, 0.1 eq), Copper Iodide (279 mg, 1.47 mmol, 0.15 eq), Sodium azide (1.27 g, 19.59 mmol, 2.0 eq) , Et3N (1.64 mL, 11.75 mmol, 1.2 eq) and 3-(prop-2-yn-l-yloxy)oxetane (9, 1.10 g, 9.80 mmol, 1.0 eq) in Methanol (24 mL) and water (6 mL) were purged with Nitrogen for 5 minutes and heated to 55 C for over night. The reaction mixture was cooled to room temperature and filtered through a plug of Celite and rinsed with Methanol (3 x 50 mL). Celite was added to the filtrate and the solvent was removed under reduced pressure. The residue was purified over silica gel (120 g) using dichloromethane/(methanol containing 12 % (v/v) aqueous ammonium hydroxide) as mobile phase. The concentration of (methanol containing 12 % (v/v) aqueous ammonium hydroxide) was gradually increased from 0 % to 25 % to afford (4-(4- ((oxctan-3-yloxy)mcthyl)-l //-l ,2,3-triazol- 1 -yl)phcnyl)mcthanaminc (32, 1.43 g, 56%) as an oil. LCMS m/z: [M + H]+ Calcd for C13H16N4O2 261.1346; Lound 261.1342.

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; SIGILON THERAPEUTICS, INC.; SMITH, Devyn, McKinley; PERITT, David; VEISEH, Omid; HEIDEBRECHT, Richard; MILLER, Robert, James; (173 pag.)WO2019/195056; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 624-76-0, A common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, molecular formula is C2H5IO, 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.

General procedure: To a solution of protected intermediate 39 (1 eq.) in anhydrous DMF (5mL/mmol) under argon were successively added potassium fluoride (2 eq.) and the appropriate alkyl iodide (1.5 eq.). The resulting mixture was stirred at rt until full conversion of the starting material, as assessed by LCMS and TLC. The mixture was then diluted with water and extracted twice with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated. The product was obtained by purification by flash column chromatography. KF could be substituted to TBAF if necessary.

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; Baud, Matthias G.J.; Bauer, Matthias R.; Verduci, Lorena; Dingler, Felix A.; Patel, Ketan J.; Horil Roy, Deeptee; Joerger, Andreas C.; Fersht, Alan R.; European Journal of Medicinal Chemistry; vol. 152; (2018); p. 101 – 114;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 39998-81-7, The chemical industry reduces the impact on the environment during synthesis 39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene, I believe this compound will play a more active role in future production and life.

To a solution of 2-fluoro-4-iodotoluene (2.83 g, 12 mmol) in CCl4 (120 mL) were added NBS (2.24 g, 12.6 mmol) and BPO (0.06 g, 0.24 mmol). The reaction mixture was refluxed for 9 h under N2, then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE) to give the title compound as a white solid (2.16 g, 57%).

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-Fluoro-4-iodo-1-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Yingjun; Zhang, Jiancun; Wang, Xiaojun; Lin, Runfeng; Cao, Shengtian; Wang, Zhaohe; Li, Jing; US2015/87639; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 883502-14-5, A common heterocyclic compound, 883502-14-5, name is 1-Fluoro-2-iodo-3-methylbenzene, molecular formula is C7H6FI, 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.

A 10 L round bottom flask equipped with adapter, thermocouple and stir bar was charged with DMA (6 L) and degassed under vacuum and purged with N2 three times. To the mixture was added Palladium Tetrakis triphenylphosphine (87.5 g, 72.0 mmol) and the mixture was degassed under vacuum and purged with N2 three times. The reaction was heated to 80 C for 30 min. 3-Fluoro-2-iodotoluene (575 g, 2.4 mol) and Zinc Cyanide (171.7 g, 1.46 mol) were added and the mixture was degassed under vacuum and purged with N2 three times. The reaction mixture was heated to 80 C for 16 h and then allowed to cool to RT. The solution was added to a 2.0 L aqueous solution of IN NH4OH and extracted three times with 1.5 L EtOAc. The extracts were washed with 2 L brine, dried over Na2S04, filtered and concentrated. The crude product was treated with mCPBA in cooled DCM and then purified by chromatography (PE/EA = 10: 1) to get the title compound.

The synthetic route of 883502-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PIO, Barbara; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; WALSH, Shawn; WO2013/90271; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 58755-70-7,Some common heterocyclic compound, 58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, molecular formula is C7H6INO3, 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.

General procedure: Arene (0.10 mmol, 1.0 equiv), Pd(OAc)2 (2.2 mg, 10 mumol,10 mol%), ligand (15 mol% or 20 mol%), hydrogen phosphate (15 mol% for benzylamine substrate), aryl iodide (0.3 mmol, 3.0 equiv.) and silver acetate (50 mg, 0.30 mmol, 3.0 equiv.) were added into a 2-dram reaction vial. Solvent and (+)-NBE-CO2Me (20 mol% or 50 mol%) were added to the mixture. The vial was flushed with N2 and capped. The reaction mixture was then stirred at the selected temperature for 12-24 h. After cooling to room temperature, the mixture was filtered through Celite and eluted with ethyl acetate. The filtrate was evaporated under reduced pressure. Purification by preparative thin-layer chromatography afforded the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-4-methoxy-2-nitrobenzene, its application will become more common.

Reference:
Article; Shi, Hang; Herron, Alastair N.; Shao, Ying; Shao, Qian; Yu, Jin-Quan; Nature; vol. 558; 7711; (2018); p. 581 – 585;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com