Month: June 2021

69113-59-3, name is 3-Iodobenzonitrile, 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. Computed Properties of C7H4IN

General procedure: A mixture of substituted iodobenzene (2 mmol), (5-formylfuran-2-yl)boronic acid (420 mg, 3mmol, 1.5 equiv), Pd(Ph3P)2Cl2 (0.1 mmol, 0.05 equiv, 70 mg) and potassium carbonate (6 mmol,3 equiv, 828 mg) in dioxone/H2O (6 mL/2 mL) was stirred at 100 C under argon atmosphereuntil the starting material was consumed (typically 20 h). The reaction mixture was then diluted with 25 mL of saturated brine. The mixture was then extracted with EtOAc (25 mL × 2), and the organic layers were combined, dried over Na2SO4. The concentrated crude product was purifie dby column chromatography to afford c2a-e. The second step is the same as procedure A.

The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Dongdong; Robinson, Elizabeth; Hom, Kellie; Yu, Wenbo; Nguyen, Nam; Li, Yue; Zong, Qianshou; Wilks, Angela; Xue, Fengtian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 6; (2018); p. 1024 – 1029;,
Iodide – Wikipedia,
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Related Products of 14452-30-3, 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 14452-30-3 as follows.

General procedure: Single-pass manner (conditions A and B): A solution of iodoarene (1mmol), alkene (2mmol), and Bu3N (condition A, 1.5mmol; condition B, 3mmol) in DMA (condition A, 10mL; condition B, 4mL) was prepared in a vial and flowed into cartridge A packed with 7% Pd/WA30 at the flow rate of 0.15mLmin-1 along with the MW irradiation (10W) under the 1MPa back-pressure in a single-pass manner. After the entire solution in the vial had passed through the catalyst cartridge, additional DMA (15mL) was passed through the path to wash out the remaining reagents (total operation time: ca. 140 min). To the collected mixture were added EtOAc (20mL) and H2O (10mL), and the layers were separated. The aqueous layer was extracted with EtOAc (20mL). The combined organic layers were washed with H2O (20mL×4) and brine (20mL), dried over Na2SO4, and concentrated in vacuo. To the residue was added CDCl3 (ca. 1.5mL) and 1,4-dioxane (8.53muL, 100mumol) as an internal standard, and the yield was determined by 1H NMR. The 1H NMR sample was diluted with EtOAc (15mL), washed three times with sat. aq. CuSO4 (5mL) and H2O (10mL), dried over Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography using hexane/EtOAc (10: 1) as the eluent to give the corresponding substituted alkenes as the Mizoroki-Heck reaction product. (0023) Circulation manner (condition C): When the TLC analysis revealed that the aryl iodide still remained unreacted after a single-pass of the reaction solution through the catalyst cartridge, both the starting and ending parts of the flow path were dipped into the reaction solution in a reservoir for circulation. After 7.5h of circulation at the flow rate of 0.15mLmin-1, the flow path was washed with DMA (15mL). The recovered mixture was treated according to a procedure similar to that described for the single-pass setup.

According to the analysis of related databases, 14452-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ichikawa, Tomohiro; Mizuno, Masahiro; Ueda, Shun; Ohneda, Noriyuki; Odajima, Hiromichi; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 74; 15; (2018); p. 1810 – 1816;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 31928-47-9, These common heterocyclic compound, 31928-47-9, name is 4-Bromo-2-chloro-1-iodobenzene, 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.

A solution of Pd(OAc)2 (0.777 g, 3.46 mmol, 0.04 equiv.) and Xantphos (3.0 g, 5.19 mmol, 0.06 equiv.) in toluene (300 mL), under N2 was stirred for 20 minutes and then added to a slurry of 6-amino-7-fluoro-3-methyl-5H-benzoimidazole-5-carboxylic acid methyl ester (6) (19.3 g, 86.5 mmol, 1 equiv.), bromochloroiodobenzene (30.2 g, 95.1 mmol, 1.1 equiv.) and Cs2CO3 (particle size = 20 microns or less; 51 g, 156 mmol, 1.8 equiv.) in toluene (200 mL), over 15 minutes at about 50 0C. The mixture was then heated at reflux for 29 hours, after which no starting material remained by HPLC analysis. After allowing the mixture to cool to ambient it was filtered through an M frit and the solid was washed with toluene (95 mL), then dried in a vacuum oven at 50 0C overnight. The solid was then suspended in water (784 mL) and 2N aqueous HCl (174 mL) was added slowly, over about 15 minutes to control bubbling. The resultant slurry was stirred at room temperature for 2 hours, then filtered through an M frit funnel (150 mL). The solid product was washed with water (3 x 87 mL) and dried in a vacuum oven at 45 0C, to provide 6-(4-bromo-2- EPO chlorophenylaminoj-V-fluoro-S-metliyl-SH-benzoimidazole-S-carboxylic acid methyl ester (11) 25.6 g (92 wt % by HPLC, corrected mass = 23.6 g, 66% yield). 1H NMR (400 MHz, d6 DMSO) delta 3.84 (3H, s, NMe), 3.93 (3H, s, OMe), 6.44 (IH, dd, J 8.8, 5.1, Ar-H), 7.28 (IH, dd, J 2, 9.8, Ar-H), 7.64 (IH, d J2.1, Ar-H), 8.1 (IH, s, NH) 8.14 ( IH, s, Ar-H), 8.5 (IH5 s, Ar-H); delta 19F (376 MHz, d6 DMSO) -133; 13C NMR (100 MHz, d6 DMSO) delta 32 (MeN), 52 (MeO), 109.4 (C), 109.7 (CH), 115.7 (CH), 119.1 (C), 120.7 (C), 122.5 (C, d, J 10), 130.4 (CH), 131.0 (CH), 133.4 (C, d, J 10), 135.5 (C, d, J 16), 140.8 (C), 146.0 (C-F, d, J 252), 148.6 (CH), 166.7 (COO); v^/cm”1 3401, 1700, 1506, 1274; m/z 412 and 414 (M+ and M+2) detected with MS APCI (+).

Statistics shows that 4-Bromo-2-chloro-1-iodobenzene is playing an increasingly important role. we look forward to future research findings about 31928-47-9.

Reference:
Patent; ARRAY BIOPHARMA INC.; ASTRAZENECA AB; WO2007/2157; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-76-0, name is 2-Iodoethanol, 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. Recommanded Product: 2-Iodoethanol

Cesium carbonate (3.91 g) is added to a solution of N-(4-chlorobenzyl)-4-hydroxy-2- (hydroxymethyl) thieno [[2, 3-B] PYRIDINE-5-CARBOXAMIDE] (3.49 g, prepared as described in US 6,239, 142) and 2-(2-iodoethoxy)tetrahydro-2H-pyran (2.56 g, prepared by mixing equal molar amounts [OF 2-IODOETHANOL] and 3, 4-dihydro-2H-pyran) in DMF (20 mL). The reaction mixture is stirred at [100 C FOR] 17 hours. The solvent is evaporated and the residue is dissolved in 10% CH30H in [CH2C12.] The mixture is washed with water and the organic layer is dried (MgSO4), filtered, concentrated. The crude product is crystallized from EtOAc to afford 3.8 g of the title compound as a white solid. Physical characteristics. 1H NMR (400 [MHZ,] DMSO-d6) delta 10.59, 8.71, 7.39, 7.38, 7.29, 5.79, 4. [69,] 4.58, 4.54, 4. [48,] 3.96, 3.78, 3.30, 1.54, 1.39, 1. [29 ;] MS (EI) [RNLZ] 476 [(M”), HRMS (FAB) ] 477.1245 (M+H) +.

The synthetic route of 624-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; FLECK, Bruce, Francis; WO2004/22567; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, 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 2043-57-4, category: iodides-buliding-blocks

The alcohol of formula (2-2) was synthesized by referring to JP-A-2010-280799. Concretely, 2- (perfluorohexyl) ethyl iodide (manufactured by Daikin Industries, Ltd., 5.4 g, 11.4 mmol), 4-hydroxythiophenol (1.3 g, 10.3 mmol), potassium carbonate (1.7 g, 12.0 mmol) was dissolved in acetone (50 mL) and heated under reflux for 24 hours. After filtration of the reaction mixture, the solvent was distilled off under reduced pressure by an evaporator. Ethanol was added to the residue and dissolved by heating, water was added, and the solution was cooled with ice water to precipitate crystals. The precipitated crystals were collected by suction filtration to obtain an alcohol (4.2 g, 86%) of the formula (2-2).

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, 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yamaguchi University; kamoto, Hiroaki; Morita, Yuki; (21 pag.)JP2016/175864; (2016); A;,
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. 628-21-7, name is 1,4-Diiodobutane, This compound has unique chemical properties. The synthetic route is as follows., name: 1,4-Diiodobutane

A solution of 66.1 g (500 mmol) of indan-2-one [615-13-4] and 340.9 g (1100 mmol) of 1,4-diiodobutane [628-21-7] in 500 ml of THF is added dropwise over the course of 2 h to a vigorously stirred mixture of 40.0 g (1 mol) of NaOH, 40 ml of water, 18.5 g (50 mmol) of tetrabutylammonium iodide [311-28-4] and 1500 ml of THF. When the addition is complete, the mixture is stirred at room temperature for a further 14 h, the aqueous phase is separated off, and the organic phase is evaporated to dryness. The residue is taken up in 1000 ml of n-heptane, washed five times with 300 ml of water each time and dried over magnesium sulfate. The crude product obtained after removal of the n-heptane is subjected to fractional distillation in an oil-pump vacuum (about 0.2 mbar, T about 135 C.). Yield: 83.0 g (345 mmol), 69%. Purity about 95% according to1H-NMR.

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 628-21-7.

Reference:
Patent; MERCK PATENT GMBH; STOESSEL, PHILIPP; KAISER, JOACHIM; KROEBER, JONAS VALENTIN; GROSSMANN, TOBIAS; (109 pag.)TW2016/30884; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route 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: An oven dried pressure tube was charged with haloarenes (0.5 mmol), copper(II) triflate (45 mg, 0.125 mmol), KNO2 (128 mg, 1.5 mmol) and anhydrous DMSO (0.6 mL) under nitrogen atmosphere. The tube was sealed with a teflon screw cap having mininert valve and nitrogen is purged through it for 5 min. It is stirred at room temperature for 10 min and then the temperature was gradually increased to 130 oC and is maintained at the same for 48 h. The reaction mixture was then cooled to room temperature, washed with excess ice cold water and extracted with ethyl acetate (3 x 10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product which was purified by column chromatography using silica gel (Table 2, entries 1-18) or basic alumina (Table 2, entries 19-23) and a mixture of ethyl acetate and hexane as the eluent to afford the desired products in good yields.

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; Amal Joseph; Priyadarshini; Lakshmi Kantam; Maheswaran; Tetrahedron Letters; vol. 53; 12; (2012); p. 1511 – 1513;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 640280-28-0,Some common heterocyclic compound, 640280-28-0, name is 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF3I, 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-bromo-2-iodo-4-(trifluoromethyl)benzene (2g, 5.70 mmol) in 10 mldry THF was slowly added isopropylmagnesium chloride (2.85 ml, 2M solution, 5.70mmol) at -10 C and reaction mixture was stirred for next 30 mm. Then the solution of dihydro-2H-pyran-4(3H)-one (0.63 g, 6.27 mmol) in 10 ml THF was added to the reaction mixture and stirred further for 1 .5h. After completion of reaction as indicated by TLC, reaction mixture was quenched by adding saturated NH4C1 solution and partitionedbetween ethyl acetate and water. The organic phase was washed with brine, dried over Na2SO4 and concentrated under vacuum. The crude was purified by column chromatography to obtain title compound (0.55g, 29 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; LUPIN LIMITED; RAMDAS, Vidya; LORIYA, Rajeshkumar, Maganlal; BANERJEE, Moloy; PATIL, Pradeep, Rangrao; JOSHI, Advait, Arun; DATRANGE, Laxmikant, Shamlal; WALKE, Deepak, Sahebrao; KHAN, Talha, Hussain; DAS, Amit, Kumar; GOTE, Ganesh, Navinchandra; KALHAPURE, Vaibhav, Madhukar; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (234 pag.)WO2017/37682; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 5460-32-2,Some common heterocyclic compound, 5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, molecular formula is C8H9IO2, 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 stirred solution of 1-iodo-3,4-dimethoxybenzene 8 (0.132g, 0.5mmol) in DMF (2.0mL) were added acrolein diethyl acetal (0.229mL, 1.5mmol), nBu4NOAc (0.302g, 1.0mmol), K2CO3 (0.104g, 0.75mmol), and Pd(OAc)2 (0.003g, 0.015mmol) and the mixture was stand for 4hat 90°C. After that period, the mixture was cooled, hydrochloric acid 2N was slowly added and the reaction was stirred at room temperature for 10min. Then, the mixture was diluted with ethyl ether (50mL) and washed with water (3×50mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane as eluent to give the desired (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde 9 in good yield (77mg, 80percent). 4.9.1 (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde (9) (0045) M.p. 80?82°C. 1H NMR (300MHz, CDCl3): delta 3.93 (s, 3H, 3-OCH3), 3.94 (s, 3H, 4-OCH3), 6.62 (dd, 1H, H-alpha, J 15.8, 7.8Hz), 6.91 (d, 1H, H-5, J 8.3Hz), 7.08 (d, 1H, H-2, J 2.0Hz), 7.17 (dd, 1H, H-6, J 8.3, 2.0Hz), 7.42 (d, 1H, H-beta, J 15.8Hz), 9.66 (d, 1H, CHO, J 7.8Hz) ppm. 13C NMR (75MHz, CDCl3): delta 55.8 and 55.9 (3,4-OCH3), 109.7 (C-2), 111.0 (C-5), 123.3 (C-6), 126.6 (C-alpha), 126.9 (C-1), 149.3 (C-3), 151.9 (C-4), 152.8 (C-beta), 193.5 (CHO) ppm. MS m/z (ESI+, percent): 193 ([M+H]+, 95), 215 ([M+Na]+, 100). HRMS (ESI+) m/z calcd. for C11H13O3 [M+H]+ 193.0859; found 193.0855.

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-dimethoxybenzene, its application will become more common.

Reference:
Article; Proenca, Carina; Albuquerque, Helio M.T.; Ribeiro, Daniela; Freitas, Marisa; Santos, Clementina M.M.; Silva, Artur M.S.; Fernandes, Eduarda; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 381 – 392;,
Iodide – Wikipedia,
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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. 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 216393-67-8

Step 2: synthesis of 4-chloro-2-fluoro-6-iodo-N-[2-(methylsulfonyl)ethyl]aniline A mixture of 4-chloro-2-fluoro-6-iodoaniline (0.5 g, 1.8 mmol), vinylmethylsulfone (0.2 g, 1.8 mmol), Cs2CO3 (1.17 g, 3.6 mmol) and DMF (15 mL) was heated with stirring at 50 C. overnight. The resulting mixture was poured into water and then extracted with EA (50 mL*3). The combined organic phases were dried over Na2SO4 and then concentrated. The residue was purified by column chromatography (EtOAc:PE=1:40) to give 4-chloro-2-fluoro-6-iodo-N-[2-(methylsulfonyl)ethyl]aniline (0.42 g, yield: 61%).

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; Hoffmann-La Roche Inc.; Feng, Song; Gao, Lu; Hong, Di; Wang, Lisha; Yun, Hongying; Zhao, Shu-Hai; US2015/158879; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com