Category: 21740-00-1

Synthetic Route of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), /V-(3-dimethylaminopropyl)-A^- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazoe (135 mg, 1.0 mmol), 7V,/V-diisopropylethylamine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na?.S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM ::: 0 : 100 to 30 : 70) to give JV-benzyl- 5-bromo-2-iodobenzamide (361 mg, 87 %) 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 5-Bromo-2-iodobenzoic acid, 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.)WO2019/164948; (2019); 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. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-2-iodobenzoic acid

A solution of 5-bromo-2-iodobenzoic acid (5. 00g, 15. [3MMOL)] in dimethylformamide [(60ML)] was treated with EDAC. [HC1] (3.. [51G, 18. 4MMOL), 1-] [HYDROXYBENZOTRIAZOLE] hydrate (2. [48G,] 18. 4mmol), and 4-aminomethylbenzoic acid tert-butyl ester (3.74g, 18. [4MMOL),] then stirred overnight at room temperature. The solution was treated with water [(40ML),] saturated aqueous sodium bicarbonate solution (15mL), followed by water [(40ML)] and the mixture stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and allowed to air dry overnight. The solid was heated in hexanes/ethyl acetate 2: 1, cooled to room temperature, and the crystals collected by filtration. Drying afforded the product as 6.30g of white solid (79.8% yield). [1H-NMR] [(CDC13)] ; d 7.98-7. 96 (d, [2H),] 7.70-7. 68 (d, 1H), 7.53-7. 52 (d, [1H),] 7.44-7. 43 (d, [2H),] 7.24-7. 21 (dd, 1H), 6.13 (bs, 1H), 4.67 (d, 2H), 1.60 (s, [9H).] MS: M+ +1 = 515.9/517. 9 Da.

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 21740-00-1.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/14379; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 21740-00-1, 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 21740-00-1 as follows.

General procedure: A mixture of 2-iodobenzoic 1a (0.2 mmol), acetylacetone 2a (0.4 mmol), and Cs2CO3 (65.2 mg, 0.20 mmol) in CH3CN was stirred at 100 C. When the reaction was considered complete as determined by TLC analysis, the reaction was allowed to cool to room temperature and quenched by water, and the mixture was extracted with CH2Cl2. The combined organic extracts were washed with water and saturated brine. The organic layers were dried over Na2SO4, filtered. Solvents were evaporated under reduced pressure. The residue was purified by chromatography on silica gel to afford isocoumarins derivatives and isoquinolone derivatives.

According to the analysis of related databases, 21740-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Lei; Hu, Jie; Wang, Xiang-Chuan; Zhong, Mei-Jin; Liu, Xue-Yuan; Yang, Shang-Dong; Liang, Yong-Min; Tetrahedron; vol. 68; 27-28; (2012); p. 5391 – 5395;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 21740-00-1, These common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, 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: A sealed tube was charged with CuCl (0.02 mmol), BFMO (0.02 mmol), N-protected N-alkenylhydrazine (2.0 mmol), 2-iodobenzoic acid (2.4 mmol), and K2CO3 (4 mmol). The tube was evacuated and backfilled with argon three times before anhydrous DMSO (4.0 mL) was added via syringe (NOTE: for liquid substrates, they were added into the tube via syringe after the tube was backfilled with argon). The mixture was sealed and stirred at 80 C for 24 h. The mixture was diluted with EtOAc, washed with water, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated in vacuo and the residue was treated with 4M HCl/1,4-dioxane (1.2 mL) at 80 C. After the starting material was completely consumed, the solution was cooled and diluted with EtOAc. The resultant mixture was washed with water and dried over anhydrous sodium sulfate. After the solution was concentratedin vacuo, the residue was purified by flash chromatography to afford the corresponding indole.

The synthetic route of 21740-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Quanpeng; Wang, Yunhan; Zhao, Jinlong; Zhang, Xiaojing; Ma, Dawei; Tetrahedron; vol. 76; 1; (2020);,
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. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-iodobenzoic acid

General procedure: The reaction of 2-iodobenzoic acid derivatives 1 and carbodiimides derivatives 2 is representative: A round bottom flask was added with 2-iodobenzoic acid derivatives 1 (0.50 mmol), carbodiimides derivatives 2 (1.0 mmol), Cu2O (0.25 mmol), in DMSO (2.5 mL). The reaction mixture was allowed to stir at 90 C for 18 hours. After completion of reaction, the reaction mixture was cooled to room temperature, quenched with 1M HCl, extracted with EtOAc, and DMSO was moved by distilled water. The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography to provide quinazolinediones derivatives 3.

The synthetic route of 21740-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Duangjan, Chanikan; Rukachaisirikul, Vatcharin; Saithong, Saowanit; Kaeobamrung, Juthanat; Tetrahedron Letters; vol. 59; 39; (2018); p. 3537 – 3540;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

Part 2, Step A: A mixture of 5-bromo-2-iodobenzoic acid (12.6 g, 38.5 mmol), but-3- yn-2-ol (3.1 mL, 2.96 g, 42.4 mmol), ZnCl2 (5.2 g, 38.5 mmol), Pd(Ph3P)4 (2.23 g, 1.9 mmol), Et3N (16.0 mL, 11.7 g, 115.5 mmol) and DMF (80 mL) was stirred under argon at 80 C for 2 hours. After removal of the volatiles under vacuum, the residue was chromatographed (silica gel, ethyl acetate in hexanes, 0-100%) to provide the intermediate 7-bromo-3-(l-hydroxyethyl)- lH-isochromen-l-one as a brown oil (7.5 g, 72%). 1H NMR (500 MHz, CHLOROFORM- ) delta ppm 8.38-8.45 (1H, m), 7.81 (1H, dd, J=8.35, 2.05 Hz), 7.32 (1H, d, J=8.51 Hz), 6.52-6.59 (1H, m), 4.66 (1H, qd, J=6.52, 0.95 Hz), 1.54-1.60 (3H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; DAKKA, Amal; KARP, Gary Mitchell; LI, Chunshi; NARASIMHAN, Jana; NARYSHKIN, Nikolai; WEETALL, Maria L.; WELCH, Ellen; ZHAO, Xin; WO2013/112788; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), /V-(3-dimethylaminopropyl)-A^- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazoe (135 mg, 1.0 mmol), 7V,/V-diisopropylethylamine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na?.S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM ::: 0 : 100 to 30 : 70) to give JV-benzyl- 5-bromo-2-iodobenzamide (361 mg, 87 %) 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 5-Bromo-2-iodobenzoic acid, 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.)WO2019/164948; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), /V-(3-dimethylaminopropyl)-A^- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazoe (135 mg, 1.0 mmol), 7V,/V-diisopropylethylamine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na?.S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM ::: 0 : 100 to 30 : 70) to give JV-benzyl- 5-bromo-2-iodobenzamide (361 mg, 87 %) 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 5-Bromo-2-iodobenzoic acid, 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.)WO2019/164948; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 21740-00-1, 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 21740-00-1 as follows.

2-(2-r(T2i?.5i?V5-([(‘5-Fluoropyridin-2-v?oxylmethvU-2-methylpiperidin-l-yl)carbonyll-4- methylphenvUpyrimidine (E-5)The solution of D-9 (1 kg, 4.46 mol) was charged in a visually clean and dry 50 L flask equipped with a thermocouple and mechanical stirrer and was solvent switched to DCM (11.00 L). DIPEA (2 L, 1 1.45 mol) is added and then EA (1.22 kg, 5.67 mol) was added to this stirring solution. This solution was cooled with an ice bath (12 C). To this stirring solution was added T3P (7.87 L, 13.38 mol) through an addition funnel keeping the reaction temperature <21 0C over Ih. Once addition was completed, the reaction became yellow and heterogenous. To facilitate stirring 2L of DCM were added. The reaction was heated to 44 0C (small exotherm at 42C, which causes the temperature to rise to 46.7 C and maintain that temperature for 30 min). The reaction was aged at this temperature overnight. After 17 h the reaction was not complete and T3P (1.1 L, 1.870 mol) was added to accelerate conversion. The next day (42 h) the reaction was deemed complete by HPLC and was cooled in an ice bath to 4 C. 20 L of water was added (slowly for the first 1.5 L then pretty fast.) keeping the reaction temperature under 17 0C. This mixture was stirred at room temperature for 30 minutes. Then the mixture was transferred into a 50 L extractor charged with 20 L of MTBE. The flask was rinsed with an additional 2 L of water and 4 L of MTBE. The layers were cut and the organics are washed with 20 L IN NaOH and then 10 L of IN NaOH. Finally, the organics were washed twice with 10 L of brine 15%. The organic fractions (quantitative HPLC assay at 1.65 kg) are then treated with ~50w% of Darco KB (75Og) for 1.75 h, filtered on Solka floe and rinsed with 10 mL/g of MTBE (1.559 kg, 94.5% recovery). To a visually clean and dry 50 L RBF equipped with a mechanical stirrer, a thermocouple, a reflux condenser and a nitrogen inlet was charged the crude material from above (E-5 solution and all solvents used were filtered using a 1 mum in-line filter). The reaction mixture was solvent switched to IPAc and the final volume was adjusted to 7.5 L (about 4 mL/g of IPAc). The reaction mixture was warmed to 75 0C (all soluble), cooled to room temperature slowly and seeded at 45 0C with 18 g OfE1S (front run material, obtained from rex in IP Ac/heptane) stirred overnight (16 hr) at room temperature then heptane was added (6 ml/g) over 60 min. The reaction mixture was aged for 1 hr before to be cooled to 5 0C and stirred for 30 min. The suspension was then transferred onto a filter pot and rinsed with IPAC/heptane (2 x 3mL/g of cold 15% IPAc) and heptane (5 mL/g). The residual beige solid was dried under a flow of nitrogen for 18 hr (the product was found to be dry with < 0.3 wt% of solvents). 1.2 kg of E-5 was isolated as a light beige solid (99.4 LCAP, > 99.5 % ee, > 99.5 % dr, Pd level of 8 ppm and KF of 0.1). Data for E^: HRMS m/z (M+H): 421.2067, found. 421.2035, required.

According to the analysis of related databases, 21740-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/147518; (2008); 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. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., COA of Formula: C7H4BrIO2

C. N, N-DIMETHYL-5-BROMO-2-IODOPHENYLACETAMIDE 5-Bromo-2-iodobenzoic acid (100 g, 0.306 mol) is dissolved in THF (350 mL) and cooled in an ice bath. Borane-THF complex (460 mL of 1 M in THF, 0.460 mol) is added dropwise. After addition is complete, the reaction is warmed to room temp and stirred for 14 hours. The mixture is transferred a large ERLENMEYER FLASK (4 L), cooled in an ice bath and carefully quenched with water (250 mL). Evaporation of the THF by rotary evaporator gives a white suspension which is treated with additional water (1 L) and then filtered and dried in a vacuum dessicator over P205 to give 5-bromo-2-iodobenzyl alcohol. The above benzyl alcohol is dissolved in 48% HBr (500 mIL and heated at reflux temperature for 4 hours. The resulting benzyl bromide is isolated as a yellow solid by pouring the cooled mixture into a large volume (1.5 L) of water followed by filtration. The benzyl bromide is dissolved in EtOH (400 mL) and stirred at room temperature. Sodium cyanide (56 g, 1.14 mol) is dissolved in a minimum amount (-100 mL) of water and then added to the ethanolic solution of the benzyl bromide. The reaction is heated to reflux temperature for 3 hours and then cooled to room temperature. Ethanol is removed by rotary evaporator and the residue washed with a large volume (1 L) of water. The resulting 5-bromo-2-iodophenylcetonitrile is isolated by filtration. The above phenylacetonitrile is dissolved in ETOH (350 mL) and treated with NAOH (32 g, 0.8 mol) which had been dissolved in water (200 mL). The reaction is heated at reflux temperature for 14 hours. After cooling to room temperature, ethanol is removed by rotary evaporator and 6 N HCI added until the pH = 1. The solid 5-bromo-2-iodophenylacetic acid that formed is filtered and washed with water (2 x 500 mL). After drying over P205 in a vacuum dessicator, 5-BROMO-2-IODOPHENYLACETIC acid (m. p. 165-169C) (102 g, 0.3 mol) is dissolved in CH2CI2 (450 mL) that contains several drops of DMF. Thionyl chloride (32 mL, 0.450 mol) is added and the reaction heated to reflux temperature overnight. After cooling to room temperature, the reaction mixture is diluted with additional CH2CI2 (500 mL) and washed with water (2 x 250 mL), saturated NAHCO3 (250 mL) and brine (250 mL). The solution is dried (MGS04) and concentrated by rotary evaporator to give 5-bromo-2- iodophenylactetyl chloride as a yellowish oil. Dimethylamine (200 mL of 2 M in THF) is added dropwise to a solution of the above 5-bromo-2-iodophenylacetyl chloride in ET20 (500 mL), cooled in an ice bath. After the addition is complete, EtOAc (350 mL) is added and the solution washed with water (350 mL), brine (250 mL) and dried (MGS04). Evaporation by rotary evaporator and trituration with 1: 1 ET2O/HEXANES GIVES N, N-DIMETHYL-5-BROMO-2-IODOPHENYLACETAMIDE (m. p. 127-129C).

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/48314; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com