Category: iodides-buliding-blocks

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. 351003-36-6, name is 2-Fluoro-5-iodobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3FIN

General procedure: 2-Fluoro-5 – [(4-hydroxy- 1 – { 4-( lH-tetrazol- 1 -yDphenyl] acetyl) piperidin-4- yl)ethynyl]benzonitrile 2-Fluoro-5-iodobenzonitrile (0.41 mg, 1.7 mmol), triphenylphosphine (0.088 g, 0.33 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.076 mg, 0.084 mmol) were dissolved in THF (15 ml) and flushed with nitrogen. The mixture was treated with l-(4-ethynyl-4-hydroxypiperidin-l- yl)-2-[4-(lH-tetrazol-l-yl)phenyl]ethanone (520 mg, 1.7 mmol) followed by tetrabutylammonium fluoride solution in THF (1.0 M, 3.3 ml, 3.3 mmol), sealed and placed in an oil bath at 60 C for 3 h. The mixture was cooled, diluted with water and ethyl acetate, and the layers separated. After the aqueous was extracted with additional ethyl acetate (2x), the combined organics were washed successively with water (2x) and brine, dried (Na2S04) and concentrated. The resulting residue was purified by MPLC (eluent gradient 10->50% EtOAc:hex.) to provide 2-fluoro-5-[(4-hydroxy-l-{[4-(lH-tetrazol-l-yl)phenyl]acetyl}piperidin- 4-yl)ethynyl]benzonitrile. 1H NMR (500 MHz, CDC13, delta in ppm): 9.04 (s, 1H), 7.72 (d, J= 8.5 Hz, 2H), 7.70 (m, 1H), 7.67 (m, 1H), 7.52 (d, J= 8.5 Hz, 2H), 7.24 (dd, J= 8.5, 8.5 Hz, 1H), 4.03 (m, 1H), 3.88 (s, 2H), 3.80 (m, 1H), 3.66 (m, 1H), 3.56 (m, 2H), 2.02 (m, 2H), 1.89 (m, 2H). LC-MS (IE, m/z): 431 [M+l]+.

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; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); 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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,2-Difluoro-4-iodobenzene

General procedure: A vial was charged with 2-Hydroxy-4-methoxybenzaldehyde (1.97 mmol, 300 mg), PdCl2 (5 mol%, 17.5 mg), 1,2-Difluoro-4-iodobenzene (2 equiv., 946.7 mg), Na2CO3 (2 equiv., 418.1 mg), LiCl (0.4 equiv., 16.7 mg), and DMF (19.7 mL, 0.1 M of the aldehyde), purged with N2 and stirred at 110 C 4-10 h. The reaction was monitored with LC-MS and TLC (TLC conditions: Aliquot was diluted with CH3OH, eluted with EtOAc/heptane 1:3, and stained with 2,4- dinitrophenylhydrazine solution). The reaction mixture was filtered over a pad of Celite, diluted with EtOAc, washed 3 times with water, and the aqueous layers was acidified and extracted twice with EtOAc. The combined organic layers was dried over Na2SO4, concentrated and purified on silica using EtOAc/Heptane 1:20 ? 1:9 step gradient) to afford 2′-hydroxybenzophenone in 69.3% yield. (NMR data is given in the supporting information).

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; Saleeb, Michael; Mojica, Sergio; Eriksson, Anna U.; Andersson, C. David; Gylfe, Asa; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1077 – 1089;,
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. 19099-54-8, name is 1-Iodo-2-isopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 19099-54-8

0.3 mmol of sodium carbonate, 0.1 mmol of 1,2-bis(4-fluorophenyl)acetylene, 0.005 mmol of palladium acetate, 0.005 mmol of bis(2-diphenylphosphinophenyl)ether, and 0.15 mmol of boronic acid pinacol ester. 0.15 mmol of 2-isopropyliodobenzene and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube, and the nitrogen was repeatedly filled 10 times, placed in an oil bath at 120 C for 24 hours; cooled to room temperature. The reaction solution was diluted with ethyl acetate and washed with water three times.Dry the organic phase with anhydrous Na2SO4, filter, concentrate, thin layer chromatographyPurification afforded 34.1 mg of the desired product in a yield of 71%. The nuclear magnetic and high resolution mass spectra of this compound were characterized as follows:

According to the analysis of related databases, 19099-54-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (10 pag.)CN109879899; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6828-35-9, name is 5-Chloro-2-iodoaniline, 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

General procedure: A mixture of o-iodoaniline (0.5 mmol, 1 equiv), arylacetic acid (0.6 mmol), elemental sulfur (1.5mmol), Cu(OAc)2¡¤H2O (20 mmol%), and NaOH (1.0 mmol) in DMSO (3 mL) was put into a sealed pressure vessel (25 mL) containing a magnetic stirring bar. The tube was purged with nitrogen three times, and then capped and stirred in a preheated oil bath at 130 C for 24 h. The reaction mixture then cooled to room temperature and extracted with ethyl acetate (3×10 mL), the organic layer was washed with saturated NaCl (2×10 mL), dried over anhydrous Na2SO4, evaporated under vacumm and then purified by silica gel column chromatography by using petroleum ether and ethyl acetate (PE:EA=200:1) as eluent.

The synthetic route of 6828-35-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xin; Li, Xiaotong; Hu, Renhe; Yang, Zhao; Gu, Ren; Ding, Sai; Li, Pengyi; Han, Shiqing; Synlett; vol. 29; 2; (2018); p. 219 – 224;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 127654-70-0,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.

To a solution of 1-chloro-3-fluoro-2-iodobenzene (0.335 g, 1.30 mmol) in tetrahydrofuran (1.5 mL), isopropylmagnesium chloride lithium chloride (0.878 ml, 1.3 M solution) was added at -10 C and the resulting mixture was stirred for 1 hour before a solution of 3 -(8-(bis(4-methoxybenzyl)amino)-2-formyl-5 -(pyrimidin-4-yl)-[1,2,4jtriazolo[1,5-ajpyrazin-6-yl)benzonitrile (0.190 g, 0.326 mmol) (from Example49 step 8) in THF (1.5 mL) was added at -10 C. The reaction mixture was stirred for60 minutes, then quenched with ammonium chloride solution (3 mL), and extractedwith dichloromethane. The combined organic layers were concentrated undervacuum. The cmde material was directly purified by a silica gel column to afford thedesired product (147 mg, 63%) as a racemic mixture. LC-MS calculated forC39H31C1FN803 (M+H): m/z = 713.2; found 713.3.

The synthetic route of 127654-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; HOANG, Gia; WANG, Xiaozhao; CARLSEN, Peter Niels; GAN, Pei; LI, Yong; QI, Chao; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHU, Wenyu; (333 pag.)WO2020/10197; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 31928-46-8, 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. 31928-46-8 name is 2-Bromo-1-chloro-4-iodobenzene, 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.

To a solution of 2-Bromo-l-chloro-4-iodo-benzene (1 1.8 g, 37.2 mmol) and but-3-yn-l-ol (2.9 g, 40.9 mmol) in dried triethylamine (50 mL) was added copper (I) iodide (1.4 g, 7.4 mmol) and then bis(triphentlphosphine)palladium (II) dichloride (3.0 g, 3.7 mmol). The mixture was degassed by nitrogen for 3 times and then kept stirred at 90 C for 5 h. The resulting mixture was diluted with EtOAc and then filtered. The filtrate was concentrated under reduced pressure and purified via flash-chromatography on silica gel (10 % EtOAc in petroleum ether) to give 4-(3-Bromo-4-chloro-phenyl)-but-3-yn-l-ol (7.4 g, yield 77 %) as white solid. MS ESI calc’d. For Ci0H8BrClO [M + H]+ 261, found 261.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-chloro-4-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ANDRESEN, Brian, M.; ANTHONY, Neville, J.; MILLER, Thomas, A.; WO2014/74422; (2014); 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. 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, A new synthetic method of this compound is introduced below., Product Details of 2043-57-4

1-Methylimidazole (4.32 g, 0.52 mol) was partially dissolved in reagent-grade toluene (50 ml) in a large round-bottomed flask and stirred vigorously. 1,1,1,2,2,3,3,4,4,5,5,6, 6-Tridecafluoro-8-iodooctane (26 g, 0.053 mol) was added, and the mixture was heated under reflux at 110 degrees C for 24 hours. The solvent was removed under vacuum giving l-methyl-3- (3,3,4,4,5,5,6,6,7,7,8,8,8- tridecafluorooctyl) imidazolium iodide (30.5 g) as a waxy solid. Potassium 1,1,2,2- tetrafluoroethanesulfonate (TFES-K, 12 g) was added to reagent grade acetone (100 ml) in a separate round- bottomed flask, and this solution was carefully added to the l-methyl-3- (3,3,4,4,5,5, 6, 6,7,7, 8, 8, 8- tridecafluorooctyl) imidazolium iodide which had been dissolved in acetone (50 ml) . The reaction mixture was heated under reflux for approximately 16 hours. The reaction mixture was then filtered using a large frit glass funnel to remove the white KI precipitate formed, and the filtrate was placed on a rotary evaporator for 4 hours to remove the acetone. The oily liquid was then filtered a second time to yield the product, as shown by proton NMR.

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; E. I. DU PONT DE NEMOURS AND COMPANY; WO2009/32959; (2009); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 148836-41-3, name is 1-Bromo-4-chloro-2-iodobenzene, 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 148836-41-3, COA of Formula: C6H3BrClI

Step 2. Ethyl 4-(2-(5-(2-bromo-5-chlorophenyl)pyridin-2-yl)-3-cvclopropylpropanamido) benzoate (9-B) To a round bottom flask was added 9-A from step 1 , l-bromo-4-chloro-2- iodobenzene (66.0 mg, 0.208 mmol), K2CO3 (43.1 mg, 0.312 mmol) and [l ,l’-bis(diphenyl phos- phino)ferrocene]dichloropalladium (15.22 mg, 0.021 mmol) at 13C. The reaction mixture was stirred at 50C for 18 h. The mixture was filtered and concentrated. The residue was purified by preparative TLC (Si02, PE_EtOAc=2: l) to give the title compound. 1H NMR (CDCI3, 400MHz): delta 10.21 (s, 1 H), 8.71 (d, J=2.0 Hz, 1 H), 8.06 (d, J=8.8 Hz, 2 H), 7.76 – 7.88 (m, 2 H), 7.71 (d, J=8.6 Hz, 2 H), 7.43 – 7.50 (m, 2 H), 7.33 (d, J=8.2 Hz, 1 H), 4.41 (q, J=7.1 Hz, 2 H), 3.98 (t, J=7.5 Hz, 1 H), 2.03 – 2.20 (m, 2 H), 1.44 (t, J=7.1 Hz, 2 H), 0.69 – 0.81 (m, 1 H), 0.42 – 0.56 (m, 2 H), 0.19 (dd, J=9.2, 4.5 Hz, 1 H), -0.02 – 0.06 (m, 1 H). MS (ESI) m/z 529.2 (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; MERCK SHARP & DOHME CORP.; LIU, Weiguo; EDMONDSON, Scott, D.; GUO, Zhuyan; MERTZ, Eric; OGAWA, Anthony, K.; SO, Sung-Sau; SUN, Wanying; BROCKUNIER, Linda, L.; ALI, Amjad; KUANG, Rongze; WU, Heping; WO2015/183709; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 31599-61-8,Some common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, molecular formula is C8H9I, 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.

1.0 mmol of 3,4-dimethyliodobenzene,1.2 mmol sodium azide,0.15 mmol DBUAnd 0.1mmol of copper acetate were sequentially added to a reaction flask equipped with 3mL of dimethyl sulfoxide,The reaction mixture was stirred at 95 C for 2.5 h,TLC was followed until the reaction was complete,A few drops of aqueous ammonia were added to the reaction mixture,Then extracted with ethyl acetate (10 mL ¡Á 3),Then washed once with saturated saline,dry,Suction filtration,Remove the solvent,Purification by column chromatography gave the desired product,Yield 90%.

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

Reference:
Patent; Henan Normal University; Jiang Yuqin; Zhao Yaru; Ma Suhao; Li Xingfeng; Dong Wenpei; Xu Guiqing; (10 pag.)CN106588693; (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. 5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9IO2

Compound 1 was mixed with with aryliodide 2c (132.0 mg, 0.50 mmol), ortho-bromoacetophenone 1a (109.4 mg, 0.55 mmol), Pd(OAc)2 (2.2 mg, 2 molpercent), xantphos (11.6 mg, 4 molpercent), tBuOK (72.9 mg, 0.65 mmol), and dry toluene (4 mL)at 80 ¡ãC for 45 min. Silica-gel column chromatography (20g, petroleum ether/ethyl acetate, 85:15 to 80:20) furnished the title compound 3ac (155 mg, 92percent) as yellow solid, recrystallized the solid with dichloromethane/hexane, mp 74?76 ¡ãC [TLCc ontrol (petroleum ether/ethyl acetate 90:10), Rf(1a)0.55, Rf(2c)0.45, and Rf(3ac) 0.20, UV detection]. IR (MIR-ATR, 4000?600 cm1): numax2956, 2923,2852, 1697, 1587, 1512, 1463, 1422, 1259, 1154, 1140, 1025, 791, 757, 678 cm1. 1HNMR (CDCl3, 400 MHz): d7.57 (d, 1H, J7.8 Hz, Ar-H), 7.35?7.15 (m, 3H,Ar-H), 6.78 (d, 1H, J8.7 Hz, Ar-H), 6.76 (dd, 1H, J8.7 and 1.9 Hz, Ar-H),6.74 (d, 1H. J1.9 Hz, Ar-H), 4.15 (s, 2H, ArCOCH2), 3.83 (s, 3H, ArOCH3),3.82 (s, 3H, ArOCH3) ppm. 13C NMR (CDCl3, 100 MHz): 201.8 (s, Ar-C=O),148.9 (s, Ar-C), 148.1 (s, Ar-C), 141.4 (s, Ar-C), 133.5 (d, Ar-CH), 131.4 (d, Ar-CH),128.6 (d, Ar-CH), 127.2 (d, Ar-CH), 125.8 (s, Ar-C), 121.9 (d, Ar-CH), 118.6(s, Ar-C), 112.7 (d, Ar-CH), 111.2 (d, Ar-CH), 55.8 (q, 2C, 2ArOCH3), 49.0 (t, Ar-COCH2) ppm. HR-MS (ESI) m=z calculated for [C16H7916 BrO3][MH]:335.0277; found 335.0294. [C16H8116 BrO3][MH]: 337.0259; found 337.0274.

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; Krishna, Jonnada; Reddy, Alavala Gopi Krishna; Satyanarayana, Gedu; Synthetic Communications; vol. 44; 14; (2014); p. 2103 – 2111;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com