Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 69113-59-3, name is 3-Iodobenzonitrile, 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 69113-59-3, category: iodides-buliding-blocks

A mixture of tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-6-azaspiro[2.5]octane-6-carboxylate (1.50 g, 3.63 mmol), 3-iodobenzonitrile (832 mg, 3.63 mmol), potassium phosphate (2.30 g, 10.89 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (91 mg, 0.103 mmol) in water (3 mL) and dioxane (15 mL) was stirred for 2 h at 80 C under nitrogen atmosphere. The mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with petroleum ether/ethyl acetate (1:1) to afford tert-butyl 1-(3′-cyano-[1,1′-biphenyl]-4-yl)-6-azaspiro[2.5]octane-6-carboxylate (1.67 g, 93%) as a white solid. LCMS (ES, m/z): 389 [M+H]+.

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

Reference:
Patent; Forma Therapeutics, Inc.; Martin, Matthew W.; Zablocki, Mary-Margaret; Mente, Scot; Dinsmore, Christopher; Wang, Zhongguo; Zheng, Xiaozhang; (382 pag.)EP3636637; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 34883-46-0, name is 1-Iodo-2-phenoxybenzene, 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 34883-46-0, Application In Synthesis of 1-Iodo-2-phenoxybenzene

In a 2L three-necked flask,Into 44.4g (150mmol, 1.0eq.) 2- iodo diphenyl ether,Dissolved with 1000 ml of chloroform,An additional 16.8 g (300 mmol, 2.0 eq.) of potassium hydroxide was added.95.85 g (600 mmol, 4.0 eq.) of liquid bromine was added dropwise at room temperature.After the completion of the dropwise addition, the reaction was stirred at room temperature for 12 hours.The reaction was quenched with a saturated Na 2 SO 3 solution, and a large amount of solid was precipitated, stirred, suction filtered, washed with water, washed with ethanol, and recrystallized from chloroform and ethanol.Finally, 50 g of Intermediate-1 was obtained in a yield of 73.3%.

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, 1-Iodo-2-phenoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Gao Guang Semiconductor Materials Co., Ltd.; Jin Zhenyu; Qian Chao; Guo Shuai; Dai Peipei; (35 pag.)CN108101922; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

123278-03-5, name is 3-Chloro-2-iodobenzoic acid, 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. category: iodides-buliding-blocks

To a solution of 3-chloro-2-iodobenzoic acid (39.5 g, 140 mmol) in methylene chloride (500 ml) and N,N-dimethylformamide (1.083 ml, 13.98 mmol) was added thionyl chloride (20.41 ml, 280 mmol) dropwise. The mixture was stirred for 1 hour at room temperature and concentrated under reduced pressure to give 3-(3-chloro-2-iodophenyl)propanoyl chloride which was useddirectly in next step. To a stirred solution of N,N,O-trimethylhydroxylamine hydrochloride (20.47 g, 183 mmol) and 3-chloro-2-iodobenzoyl chloride (46 g, 153 mmol) in dry methylene chloride (500 ml) was added triethylamine (74.6 ml, 535 mmol) dropwise at 0C. The mixture was stirred for 4 hours at room temperature and then poured into water. The organic layer was separated, washed with water and brine, dried over Na2504, filtered and concentrated to afford the titlecompound.

The synthetic route of 123278-03-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; MICHAELIDES, Michael; HANSEN, Todd; DAI, Yujia; ZHU, Guidong; FREY, Robin; GONG, Jane; PENNING, Thomas; CURTIN, Michael; MCCLELLAN, William; CLARK, Richard; TORRENT, Maricel; MASTRACCHIO, Anthony; KESICKI, Edward A.; KLUGE, Arthur F.; PATANE, Michael A.; VAN DRIE, John H. Jr.; JI, Zhiqin; LAI, Chunqiu C.; WANG, Ce; (1190 pag.)WO2016/44770; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

61203-48-3, 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. 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

[230] b. N-(6,7-Methylenedioxyquinolin-4-yl)-N-[2-(N,N-diethylamino)ethyl]-2- iodo-4,5-dimethoxybenzamide. Oxalyl chloride (1.12 g , 8.8 mmol) was added to a solution of 2-Iodo-4,5-dimethoxybenzoic acid (820 mg, 2.6 mmol; see above) in anhydrous methylene chloride (40 mL) and the stirred mixture was refluxed for 4 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was dissolved in 40 mL of methylene chloride and added to a solution of 4-[[2-(Diethylamino)ethyl]amino]-6,7-methylenedioxyquinoline (640 mg, 2.2 mmol), and triethylamine (2.2g, 22 mmol) in methylene chloride (50 mL) and the resulting mixture was stirred at reflux under nitrogen for 2 hours. The reaction mix was cooled and washed with a saturated solution of sodium bicarbonate (3 x 75 mL), and extracted into dilute HCl (4 x 100 mL). The aqueous extract was then neutralized with 30% NaOH and extracted with CHCl3 (4 x 100 mL), washed with brine (100mL), dried (MgSO4) and evaporated, yielding 1.1 g as a sticky semisolid glue, in 86% yield; 1H NMR (CDCl3) 0.96 (t, 6H, J=7.2), 2.54 (q, 4H, J=7.2), 2.82 (m, 2H), 3.29 (s, 3H), 3.71 (s, 3H), 3.92 (m, 1H), 4.46 (m, 1H), 6.12 (s, 2H), 6.37 (s, 1H), 7.00 (s, 1H), 7.27 (d, 1H, J=4.8), 7.33 (s, 1H), 7.39 (s, 1H), 8.52 (d, 1H, J=4.8); 13C NMR (CDCl3) 11.8, 47.1, 47.5, 50.7, 55.5, 56.1, 82.7, 98.5, 102.2, 106.7, 110.6, 120.1, 121.8, 122.7, 133.7, 146.3, 148.1, 148.3, 148.5, 149.0, 149.7, 151.0, 170.0; HRMS calcd for C25H28O5N31H: 578.1153; found: 578.1153.

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; GENZYME CORPORATION; TEICHER, Beverly A.; SCHMID, Steven M.; WO2012/15875; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 20691-72-9, name is 4-Iodo-2-nitroaniline, 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 20691-72-9. 20691-72-9

General procedure: Ra/Ni (0.4-0.5 g) was added in small portions to a stirred solution of 6.5 mmol of the required nitro compound (4-11) in 12 mL EtOH, 12 mL 1,2-dichloroethane and 2 mL (20 mmol) hydrazine hydrate at 30 C. After completion of the Ra/Ni addition, the mixture was heated in a water bath (50 C, 60 min) and filtered through celite. The filtrate was evaporated in vacuo and crude product used for further syntheses.

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 4-Iodo-2-nitroaniline.

Reference:
Article; Vasic, Vesna P.; Penjisevic, Jelena Z.; Novakovic, Irena T.; Sukalovic, Vladimir V.; Andric, Deana B.; Kostic-Rajacic, Sladana V.; Journal of the Serbian Chemical Society; vol. 79; 3; (2014); p. 277 – 282;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, 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 5458-84-4, Quality Control of 1-Iodo-2-methoxy-4-nitrobenzene

A mixture of Cu l (6.80 g, 35.84 mmol ), CsF ( 14. 15 g, 93.18 mmol ) l -iodo-2-methoxy- 4-nitrobenzene ( 10 g, 35.84 mmol ) and sulfolane (20 ml ), was stirred rapidly at 45 C. To this mixture was added trimethyl(trifluoromethyl)silane ( 13.25 g, 93. 1 mmol ) dropwise over 4 hours using a syringe pump, and the resulting mixture was stirred at 45C for 1 8 hours. The mixture was diluted with ethyl acetate (500 mL ) and stirred with Celite for 5 min. The reaction mixture was filtered through a pad of Celite, diluted with ethyl acetate ( 500 mL ). The organic layer was washed with 10% NH4OH, 1.0 N HCl, brine, dried over Na2SC>4, filtered, and concentrated to give the crude product.The crude product was purified by chromatography (ethyl acetate/petroleum ether 0/1 to 1/4) to give intermediate 444 (8 g, 91% yield ) as a white solid.

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, 1-Iodo-2-methoxy-4-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 83863-33-6, name is 5-Iodo-2-methylaniline, molecular formula is C7H8IN, 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. name: 5-Iodo-2-methylaniline

General procedure: The aromatic azides are prepared (Scheme 2) by addition of 6 NHCl solution to stirring dichloromethane solution of the appropriate amine at 0 C followed by drop wise saturated aqueous solution of NaNO2 and the contents stirred for 30 min. To the reaction mixture, added NaN3 stirred the contents for further 30 min.The contents were allowed to attain room temperature, the two phases were separated, and the aqueous phase extracted with DCM. The combined organic layers were washed with aqueous solution of NaHCO3, followed by then brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the aryl azides which were used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 83863-33-6, its application will become more common.

Reference:
Article; Majeed, Rabiya; Sangwan, Payare L.; Chinthakindi, Praveen K.; Khan, Imran; Dangroo, Nisar A.; Thota, Niranjan; Hamid, Abid; Sharma, Parduman R.; Saxena, Ajit K.; Koul, Surrinder; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 782 – 792;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 6136-66-9, These common heterocyclic compound, 6136-66-9, name is (4-Iodophenyl)(phenyl)methanone, 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 74. 4-(Triethoxysilyl)benzophenone (S57)[Rh(COd)(MeCN)2]BF4 (11.0 mg, 0.0300 mmol, 0.0300 equiv) and 4- iodobenzophenone (307 mg, 1.00 mmol, 1.00 equiv) were charged in 10 mL vial capped with a rubber septum. The vial was evacuated and backfilled with nitrogen. To this vial, DMF (4 mL), triethylamine (0.420 mL, 3.00 mmol, 3.00 equiv) and triethoxysilane (0.360 mL, 2.00 mmol, 2.00 equiv) were added. The reaction mixture was stirred at 80 0C for 2 h, then cooled to 23 0C. The mixture was diluted with ether (50 mL) and washed three times with water (3 x 20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Kugelrohr distillation to give 275 mg of the title compound as a colorless oil (80% yield). R/= 0.45 (hexanes/EtOAc 3:1 (v/v)). NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23 0C, delta): 7.82-7.77 (m, 6H), 7.59 (t, / = 7.5 Hz, IH), 7.48 (dd, / = 7.5 Hz, 7.5 Hz, 2H), 3.90 (q, / = 7.0 Hz, 6H), 1.27 (t, / = 7.0 Hz, 9H). 13C NMR (125 MHz, CDCl3, 23 0C, delta): 196.84, 139.05, 137.29, 136.34, 134.66, 132.54, 130.11, 129.00, 128.28, 58.91, 18.21. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [M + Na]+, 367.13361. Found, 367.13347.

The synthetic route of 6136-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; FURUYA, Takeru; TANG, Pingping; WO2010/59943; (2010); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 19094-56-5, name is 2-Chloro-5-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. Safety of 2-Chloro-5-iodobenzoic acid

Analogous to the preparation of 4a, 2-chloro-5-iodobenzoic acid (2.81g, 10mmol) was treated with thionyl chloride (7 mL)

The synthetic route of 2-Chloro-5-iodobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhi, Ying; Gao, Li-Xin; Jin, Yi; Tang, Chun-Lan; Li, Jing-Ya; Li, Jia; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3670 – 3683;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13194-68-8, name is 4-Iodo-2-methylaniline, 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 13194-68-8, Safety of 4-Iodo-2-methylaniline

A suspension of 4,5,6-trifluoro-isophthalic acid (1.03 g, 4.68 mmol) in freshly distilled THF (20 mL) at -78 C under nitrogen is treated with 2.0 equivalents of freshly prepared 1 M LiHMDS solution (HMDS, 2.07 mL, 9.83 mmol; n-butyllithium, 3.5 mL, 9.36 mmol) in THF. In a second flask is suspended 4-iodo-2-methylaniline (1.09 g, 4.68 mmol) in 20 mL of freshly distilled THF, cooled to -78 C. under nitrogen and treated with 2.0 equiv. of freshly prepared 1M LiHMDS solution (HMDS, 2.07 mL, 9.83 mmol; n-butyllithium, 3.5 mL, 9.36 mmol) in THF. After both solutions stirred for 30 minutes at -78 C., the benzoic acid solution was cannula transferred into the aniline solution and allowed to slowly warm to room temperature. After stirring for 4 hours, the reaction mixture was poured into 200 mL of a saturated HCl diethyl ether solution affording a white precipitate. The solid is filtered off and the remaining filtrate is collected and concentrated in vacuo affording 4,5-fluoro-6-(4-iodo-2-methyl-phenylamino)-isophthalic acid (1.55 g, 77%).

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, 4-Iodo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Biwersi, Cathlin; Tecle, Haile; Warmus, Joseph Scott; US2003/225076; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com