Month: October 2020

63262-06-6, A common heterocyclic compound, 63262-06-6, name is 1,4-Dibromo-2,5-diiodobenzene, molecular formula is C6H2Br2I2, 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: In argon atmosphere, Pd(PPh3)2Cl2(115 mg, 0.164mmol) and CuI (156 mg, 0.820 mmol) were added to a stirring solutionof CuI (4.00 g, 8.20 mmol) in anhydrous THF/Et3N (30 ml, 1/1). 4-Ethyloct-1-yne(2.49 g, 18.0 mmol) was then added with a syringe. Theresulting mixture was stirred overnight at room temperature, and then pouredinto a large amount of dilute ammonia water for extraction with petroleum ether.The combined organic extracts were washed with saturated NH4Claqueous solution and brine until to neutral, dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified with column chromatographyon silica gel with petroleum ether as the eluent

The synthetic route of 63262-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shao, Jing; Zhao, Xiaoli; Wang, Li; Tang, Qingxin; Li, Weili; Yu, Han; Tian, Hongkun; Zhang, Xiaojie; Geng, Yanhou; Wang, Fosong; Tetrahedron Letters; vol. 55; 41; (2014); p. 5663 – 5666;,
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. 25252-00-0, name is 2-Bromo-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 25252-00-0

Oxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo-5-iodo-benzoic acid (49.5 g) in CH2CI2 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h. Then, the solution is concentrated under reduced pressure and the residue is dissolved in THF (100 mL). The resulting solution is cooled in an ice-bath and LiB (3.4 g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1 M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2S04) and the solvent is evaporated under reduced pressure to give the crude product. Yield: 47.0 g (99% of theory)

The synthetic route of 25252-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM VETMEDICA GMBH; REICHE, Dania Birte; MOHREN, Nicole; JOHNSTON, Laura; SOMERVILLE, Bruce; VOTH, Rebecca K.; WO2015/150299; (2015); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19094-56-5, A common heterocyclic compound, 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, molecular formula is C7H4ClIO2, 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.

2-chloro-5-iodobenzoic acid (10.0 g, 35.5 mmol) was suspended in methylene chloride (200 mL). To the resulting mixture was added N,N-dimethylformamide (0.05 mL), and then added dropwise oxalyl chloride (11.3 g, 89.0 mmol) at 0 C. After the completion of dropwise addition, the resulting mixture was warmed up to room temperature and stirred for 4 hr. The resulting clear solution was evaporated by rotation to remove the solvent and produce 10.7 g of a product in a yield of 100%, which was directly used in the next reaction without purification

The synthetic route of 19094-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Wu, Frank; US2015/191502; (2015); A1;,
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 162358-07-8 as follows. 162358-07-8

(2) Diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate To a suspension of sodium hydride (6 g) in dimethylformamide (100 ml), a solution of ethyl acetamidomalonate (33 g) in dimethylformamide (100 ml) was added under ice-cooling and the mixture was stirred at room temperature for 2 hours. A solution of 2-(4-octylphenyl)ethyl iodide (37 g) in dimethyl-formamide (100 ml) was added to the mixture under ice-cooling. The mixture was stirred for 2 hours at the same temperature and left standing overnight. The resultant mixture was poured into water and extracted with ethyl acetate. The extract was washed with a saturated brine and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel chromatography (eluent; hexane-ethyl acetate=3:1) to give the subject compound (25 g). Rf value: 0.40 (hexane-ethyl acetate=2:1) 1 H-NMR(400 MHz, CDCl:3) delta: 0.88 (3H, t, J=8 Hz), 1.20-1.30 (10H, m), 1.24 (6H, t, J=8 Hz), 1.50-1.62 (2H, m), 1.97 (3H, s), 2.45 (2H, dd, J=12, 8 Hz), 2.54 (2H, t, J=8 Hz), 2.68 (2H, dd, J=12, 8 Hz), 4.14-4.26 (4H, m), 6.75 (1H, s), 7.05 (2H, d, J=8 Hz), 7.08 (2H, d, J=8 Hz)

According to the analysis of related databases, 162358-07-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yoshitomi Pharmaceutical Industries, Ltd.; US5948820; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1643-29-4, A common heterocyclic compound, 1643-29-4, name is 3-(4-Iodophenyl)propanoic acid, molecular formula is C9H9IO2, 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.

EXAMPLE 16; Commercially available 3-(4-iodophenyl)propionic acid (200 mg, 0.72 mmol) was combined with phenyl boronic acid (177 mg, 1.45 mmol), catalytic tetrakis-(triphenylphosphine)- palladium (20 mg), and saturated aqueous sodium bicarbonate (IM5 1.45 mL, 1.45 mmol) in (1:1) dioxane-ethanol (5 mL). The reaction mixture was heated at 100 0C overnight, cooled to room temperature, filtered, and concentrated in vacuo. The residue was purified via preparative RPHPLC to give the biaryl propionic acid intermediate, which is defined as Compound 15 in Scheme 5. This intermediate acid was converted into EXAMPLE 16 in a manner similar to the Examples above. The compound was purified via preparative RPHPLC to give the desired product. 1H KfMR (CD3OD, 500 MHz) delta 7.68-7.62 (m, 4H), 7.51-7.38 (m, 5H), 6.93 (s5 IH), 3.12 (t, 2H), 2.93 (t, 2H), 2.80 (q, 2H)5 2.66 (s, IH), 1.33 (t, 3H); LCMS m/z 378 (M-I).

The synthetic route of 3-(4-Iodophenyl)propanoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/120575; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 387-48-4, name is 3-Fluoro-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. 387-48-4

Intermediate A-33: 3-fluoro-2-(1H-1,2,3-triazol-1-yl)benzoic acid To 3-fluoro-2-iodobenzoic acid (4.5 g, 16.9 mmol) dissolved in dioxane (33.8 mL) and H2O (0.09 mL) was added Cs2CO3 (11.02 g, 33.8 mmol), CuI (161 mg, 0.85 mmol), 2H-1,2,3-triazole (1.96 mL, 33.8 mmol), and trans-N,N-dimethyl-1,2-cyclohexanediamine (0.53 mL, 3.38 mmol). The mixture was then heated to 100 C. overnight, cooled to room temperature, diluted with H2O, and extracted with EtOAc. The aqueous layer was then acidified and extracted with EtOAc. The combined organics were dried and concentrated. From this concentrate a solid precipitated to provide intermediate A-33 (285 mg, 8%). MS (ESI) mass calcd for C9H6FN3O2, 207.0; m/z found 208.1 [M+H]+. 1H NMR (500 MHz, Methanol-d4) delta 6.81-6.77 (m, 1H), 6.46-6.40 (m, 2H), 6.30-6.23 (m, 1H), 6.18-6.12 (m, 1H).

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 387-48-4.

Reference:
Patent; Janssen Pharmaceutica NV; GELIN, Christine F.; LEBOLD, Terry P.; SHIREMAN, Brock T.; US2014/275118; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

766-99-4, 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 766-99-4 as follows.

A solution of 4-iodophenyleneacetylene in 0.5 mmol (113 mg)N-chlorosuccinimide 1 mmol (133 mg),Silver nitrate 1 mmol (154 mg) and tetrahydrofuran 5 ml were successively added to a 25 ml volume sealed pressure vessel.The mixture was reacted at 50 C for 8 hours.After completion of the TLC reaction, the reaction solution was diluted with methylene chloride and filtered to give a clear solution which was separated by column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio of 10: 1) The eluate was removed by evaporation of the eluent to give 1-iodo-4- (nitroalkynyl) benzene (58% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 766-99-4, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang University of Technology; Liu, Yunkui; Zhang, Wei; Zhang, Jian; (10 pag.)CN106478327; (2017); A;,
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. 455-13-0, name is 4-Iodobenzotrifluoride, A new synthetic method of this compound is introduced below., 455-13-0

General procedure: General procedure: a 50 mL ask equipped with a magnetic stir bar was charged with aryboronic acid (1 mmol, 1 equiv), aromatic halides (1.2 mmol, 1.2 equiv), catalyst (2 mol%), base (2 mmol, 2 equiv), DMF (5 mL) solution under CO (1 atm) atmosphere, along with sealed the reaction flask by a rubber stopper and CO was injected into it with a stainless steel gas flowmeter. The mixture was then stirred at 120 C forthe indicated time (SI, Fig. S1). After being allowed to cool to roomtemperature, the reaction mixture was diluted with 5 mL water and extracted with diethyl ether (3 ¡Á 5 mL). The organic phases werecombined, and the volatile components were evaporated in a rotaryevaporator. The residue was puried by column chromatography onsilica gel.

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, Zheng-Jun; Wang, Xue-Yan; Wang, Xia; Liang, Zhi-Wu; Xu, Xinhua; Catalysis Communications; vol. 101; (2017); p. 10 – 14;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

627-32-7, Name is 3-Iodo-1-propanol, 627-32-7, 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.

General procedure: 4.2.1.7 10-(3-Hydroxypropoxy)-3,9-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-2-ol (16) Yield 76%; reddish-brown solid, mp 73-78 C; 1H NMR (CDCl3, 500 MHz) 6.87-6.80 (m, 3H), 6.60 (s, 1H), 4.22 (d, J = 15.7 Hz, 1H), 4.16 (td, J = 6.1, 1.5 Hz, 2H), 3.91-3.84 (m, 8H), 3.52 (d, J = 15.4 Hz, 2H), 3.27-3.10 (m, 3H), 2.80 (dd, J = 15.7, 11.6 Hz, 1H), 2.68-2.61 (m, 2H), 2.07 (quint, J = 5.8 Hz, 2H); 13C NMR (CDCl3, 125 MHz) delta 149.4, 145.4, 145.1, 143.9, 130.5, 128.8, 128.4, 126.1, 124.1, 112.5, 111.3, 110.6, 67.5, 61.0, 60.3, 59.2, 55.9, 54.0, 51.6, 36.3, 32.1, 29.2; HRMS (ESI) m/z calcd for C22H27NO5 [M+H]+, 386.1884, found 386.1897.

Statistics shows that 3-Iodo-1-propanol is playing an increasingly important role. we look forward to future research findings about 627-32-7.

Reference:
Article; Gadhiya, Satishkumar; Madapa, Sudharshan; Kurtzman, Thomas; Alberts, Ian L.; Ramsey, Steven; Pillarsetty, Nagavara-Kishore; Kalidindi, Teja; Harding, Wayne W.; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 2060 – 2071;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, 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 2401-21-0. 2401-21-0

A solution of 2,3-dichloro-iodobenzene (6.00 G, 22. 0 mmol) in 60 mL toluene and 20 mL eth- anol was treated with 3-nitro-phenylboron. ic acid (4. 22 G, 25. 3 mmol) and NA2CO3 (2 N in H20, 30. 0 ML). Then mixture was purged with N2 for 5 min and Pd- (PPH3) (1. 02 G, 0. 879 mmol) was added. The mixture was heated to 90¡ãC for 24 h and cooled to ambient temperature and concentrated in vacuo. The residual oil was partitioned with Et2O (80 M. L) and washed with dilute brine solution (3×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The resulting white solid was recrystallized from hexane and to give the title compound (2.30 g, 39percent) as a fluffy white SOLID. 1H NMR (CDC13,400 MHz) 5 8.29 (m, 2H), 7.76 (m, 1H), 7.63 (t, J=7. 61 Hz, 1H), 7. 55 (m, 1H), 7. 31 (t, J=7.81 HZ, 1H), 7.26 (m, 1H.)

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 1,2-Dichloro-3-iodobenzene.

Reference:
Patent; ICOS CORPORATION; WO2005/19200; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com