Month: September 2021

Reference of 51839-15-7, These common heterocyclic compound, 51839-15-7, name is Dimethyl 5-iodoisophthalate, 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.

Intermediate LXII: Dimethyl-5-trifluoromethyl isophthalate; To a solution of dimethyl 5-iodoisophthalate (1 g, 3.12 mmol) in 1:1 DMF/HMPA was added Methyl- 2,2-difluoro-2( fluorosulfonyl) acetate (3 g, 15.6 mmol) and Copper (I) Iodide (2.9 mg, 15.6 mmol) and the reaction mixture heated to. 80 C for 16 h. The reaction was cooled to rt and diluted with ethyl acetate (200 mL) The solvent was decanted and the copper salts washed with an additional 100 mL of ethyl acetate. The organics were poured into water (200 mL ) the phases separated and the aqueous extracted with Ethyl acetate ( 100mL) dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane. to give dimethyl-5-trifluoromethyl isophthalate. : :¹H NMR (400 MHz, CDC13) No. 8.85 (s, 1H), 8.48 (s, 2H), 4.01 (s, 6H). LCMS [(M) +H]+ = 263.

The synthetic route of 51839-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/103020; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 127654-70-0, name is 1-Chloro-3-fluoro-2-iodobenzene, molecular formula is C6H3ClFI, 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: 1-Chloro-3-fluoro-2-iodobenzene

Step 22-Chloro-6-fluoro-iodbenzene (10 g, 39 mmol) is dissolved in sulfuric acid (cone, 17 ml_) at 0 C. A mixture of nitric acid (cone, 3.2 ml_) and sulfuric acid (cone, 3.2 ml_) is added at 0 C and stirring is continued for 2 h at 25 C. The reaction mixture is pourred onto ice. The resulting precipitate is collected, dried and used without further purification for the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127654-70-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STADTMUELLER, Heinz; WO2012/104388; (2012); 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. 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H6BrIO

To a solution of 4-bromo-1-iodo-2-methoxybenzene (1.634 g, 5.221 mmol) in dry acetonitrile (20 mL) Cul (49.7 mg, 0.261 mmol) and Pd(Ph3P)2Cl2 (183.2 mg, 0.261 mmol) were added under Argon atmosphere and the mixture was degassed and backfilled with Argon for three times. TEA (0.728 mL, 5.221 mmol) and (ethynyl)trimethylsilane(l .48 mL, 1.03 g, 10.442 mmol) were added with a syringe and the reaction mixture, that darkened within 10 min, was stirred at room temperature for 1 h. The solvent was removed under vacuum and the residue was taken up with EtOAc (100 mL), washed with brine (3 x 20 mL), water (20 mL), dried over sodium sulphate and evaporated to dryness. The crude was purified by chromatography on silica gel (petroleum ether/diethyl ether 9/1) to yield the title compound as an orange solid (1.426 g, 96.5%). 1H NMR (400 MHz, DMSO-cie) delta ppm 0.21 (s, 9 H) 3.83 (s, 3 H) 7.11 (dd, J=8.18, 1.83 Hz, 1 H) 7.26 (d, J=1.83 Hz, 1 H) 7.31 (d, J=8.06 Hz, 1 H).

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; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria, Gabriella; BERTRAND, Jay, Aaron; GNOCCHI, Paola; MOTTO, Ilaria; NESI, Marcella; PANZERI, Achille; VIANELLO, Paola; WO2013/14039; (2013); 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 723294-75-5 as follows. Application In Synthesis of 3-Fluoro-5-iodobenzonitrile

A mixture of compound 1 (15mg, 0.085mmol), compound 2(25mg, 0.1mmol), Cs2CO3 (110mg, 0.34mmol), Pd(dba)2 (5mg, 0.0085mmol) and Xanphos (4mg, 0.0085mol) in DMF(1.0mL) were degassed under N2 and then heated to 100 C for lh. After cooled, the reaction mixture was filtered. The filtrate was washed with H2O, extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to residue, which was purified by prep-TLC (EA/PE, 1/2, v/v) to give desired compound (13mg, 52% yield). LCMS: m/z, 296.1(M+H)+; 1HNMR (400MHz, CDCl3) delta 4.24~4.44(m, 4H), 6.32~6.35(m, 1H), 6.66 (s, 1H), 6.75(d, J=8.0Hz, 1H), 7.26~7.35(m, 1H), 7.50(d, J=7.6Hz, 1H), 7.64~7.73(m, 1H), 8.62(d, J=4.8Hz, 1H).

According to the analysis of related databases, 723294-75-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 612-55-5, 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. 612-55-5 name is 2-Iodonaphthalene, 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.

General procedure: The product 12a is a representative reaction. To a vial (5 mL) containing caffeine (0.5 mmol), iodobenzene (1.0 mmol), catalyst 3e (0.05 mmol), and LiOtBu (1.0 mmol) was added DMF (1.0 mL) solvent under a glovebox atmosphere. After the substances were completely dissolved, the vial was screw-capped, taken outside the glovebox and heated at 140 C for 8 h. The resulting mixture was filtered through Celite and washed with dichloromethane. The filtrate solution was concentrated in vacuo to afford the crude product, which was further purified by column chromatography using hexane/ethyl acetate as eluent to furnish 12a in 80% yield.

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

Reference:
Article; Huang, Hsuan-Jui; Lee, Wei-Chih; Yap, Glenn P.A.; Ong, Tiow-Gan; Journal of Organometallic Chemistry; vol. 761; (2014); p. 64 – 73;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 61272-76-2, A common heterocyclic compound, 61272-76-2, name is 4-Fluoro-2-iodoaniline, molecular formula is C6H5FIN, 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 55 4-(((5-Fluoro-2-(triethylsilyl)-1H-indol-3-yl)methoxy)methyl)-N,N-dimethyl-1-(thiophen-2-yl)cyclohexanamine (one of two possible diastereomers) A degassed mixture of Ain-09 (795 mg, 2 mmol), 4-fluoro-2-iodoaniline (567 mg, 2.4 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II) chloride (PEPPSI, 273 mg, 0.4 mmol) and sodium carbonate (1.06 g, 10 mmol) in anhydrous and oxygen-free N,N-dimethyl formamide (10 ml) was stirred for 18 h at 100° C. The solvent was then removed under vacuum and the residue divided between water and diethyl ether (20 ml each). The phases were separated and the aqueous phase was extracted with diethyl ether (3*10 ml). The combined organic phases were washed with water and 1 M sodium thiosulfate solution (20 ml each), dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (1.30 g) was purified by flash chromatography (100 g, 20*4.0 cm) with ethyl acetate/cyclohexane (1:9). Yield: 552 mg (55percent), brownish oil 1H-NMR (DMSO-d6): 0.82-0.98 (m, 15H); 1.30-1.70 (m, 7H); 1.96 (s, 6H); 2.37 (br d, 2H); 3.25-3.33 (m, 2H); 4.58 (s, 2H); 6.88-7.04 (m, 3H); 7.23-7.31 (m, 1H); 7.35-7.41 (m, 2H); 10.77 (s, 1H). 13C-NMR (DMSO-d6): 3.1; 7.2; 24.4; 34.6; 37.1; 37.4; 58.2; 64.4; 74.7; 102.8 (d, J=23 Hz); 109.6 (d, J=27 Hz); 112.1 (d, J=10 Hz); 121.5; 123.0; 123.8; 126.0; 128.7 (d, J=10 Hz); 135.3; 135.9; 145.0; 156.7 (d, J=231 Hz).

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; GRUNENTHAL GMBH; US2009/215725; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 387-48-4,Some common heterocyclic compound, 387-48-4, name is 3-Fluoro-2-iodobenzoic acid, molecular formula is C7H4FIO2, 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.

To a mixture of 3-fluoro-2-iodobenzoic acid (1 .4 g, 5.26 mmol), 1 H-pyrazole (0.72 g, 10.5 mmol), trans-N, N’-dimethyl-cyclohexane-1 ,2-diamine (0.17 mL, 1 .05 mmol), Cul (50.1 mg, 0.26 mmol), dioxane (50 mL) and water (0.028 mL) was added CS2CO3 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100 C for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. Purification (FCC), (DCM to 10%MeOH/1 %HOAC/DCM) afforded the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCI3): 7.85 – 7.73 (m, 1 H), 7.54 – 7.44 (m, 1 H), 7.44 – 7.34 (m, 1 H), 6.55 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 774608-49-0, A common heterocyclic compound, 774608-49-0, name is 4-Bromo-1-chloro-2-iodobenzene, molecular formula is C6H3BrClI, 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.

j00340j To a solution of 4-bromo-1-chloro-2-iodobenzene (0.30 g, 0.95 mmol), cyclopropylboronic acid (97 mg, 1.1 mmol), [1,1 ?-bis(diphenylphosphino)ferrocenej dichloropalladium(II) (39 mg, 0.047 mmol) in dioxane (6 mL) and water (2 mL) under nitrogen at room temperature was added potassium phosphate (0.76 g, 3.6 mmol). The reaction mixture was stirred at 70 C for 3 hours, then diluted with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (2 xlO mL), dried over sodium sulfate, filtered and concentrated in vacuo to give compound B-34 (0.30 g, crude) as a yellow oil.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 105202-02-6, name is 2-Iodo-5-(trifluoromethyl)aniline, 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 105202-02-6, name: 2-Iodo-5-(trifluoromethyl)aniline

To a solution of compound 53 (620 mg, 2.16 mmol) in DMF (5 mL) was added phenylacetylene (331 mg, 356 muL, 3.24 mmol), PdCI2(PPh3)2 (76 mg, 0.108 mmol), Cul (25 mg, 0.131 mmol) and Et3N (656 mg, 903 muL, 6.48 mmol) at 23 C. The reaction mixture was stirred for 6 h at 23 C before it was quenched with a saturated solution of NH4CI (10 mL) and diluted with EtOAc (50 mL). The layers were separated, and the organic layer was extracted with H20 (3 x 10 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexanes:EtOAc 5: 1 ) to give compound 54 (518 mg, 92%) as pale yellow solid. (0472) [00362] 1 H NMR (400 MHz, CDCI3) delta = 7.56 (m, 2H), 7.47 (dd, J = 8.5, 0.8 Hz, 1 H), 7.42 – 7.38 (m, 3H), 6.98 – 6.96 (m, 2H), 4.48 (brs, 2H); 13C NMR (101 MHz, CDCI3) delta = 147.8, 132.5, 131 .6, 131 .5 (q, J = 32.2 Hz), 128.7, 128.5, 124.0 (q, J = 272.3 Hz), 122.6, 1 14.3 (q, J = 3.8 Hz), 1 1 1 .2, 1 10.7 (q, J = 4.0 Hz), 96.5, 84.6; 19F NMR (376 MHz, CDCI3) delta = -63.13. m/z (ESI) 262.1 [M+H+].

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; THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO; GREIG, Iain; ZANDA, Matteo; TSENG, Chih-Chung; ROSS, Ruth; (134 pag.)WO2016/29310; (2016); A1;,
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. 61272-76-2, name is 4-Fluoro-2-iodoaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Fluoro-2-iodoaniline

General procedure: A sealed tube (50 mL) was charged with 2-haloaniline 1a (2mmol), CS2 (10 mmol), Na2S (4mmol) and DMF (2 mL) at room temperature under an argon gas atmosphere and the tube was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically at 110 °C for 12 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, 2 mL HCl (3 mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by dichloromethane (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel colum chromatography (eluent: petroleum ether / ethyl acetate) give the corresponding pure product 2a.

The synthetic route of 61272-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Tianmiao; Qin, Weijing; Zhu, Ning; Han, Limin; Wang, Liubo; Hong, Hailong; Synthetic Communications; vol. 47; 20; (2017); p. 1916 – 1925;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com