Category: iodides-buliding-blocks

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,
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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,
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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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101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, 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: 101335-11-9

The 1-(2-chloro-4-fluorophenyl)-2-piperazinone used in the above procedure was prepared as follows: A suspension of 2-piperazinone (1.5 g, 15.0 mmol), 2-chloro-4-fluoro-1-iodobenzene (3.8 g, 15.0 mmol), copper(l) iodide (0.57 g, 3.0 mmol), N,N’-dimethyl-1 ,2- cyclohexanediamine (1.3 g, 6.0 mmol), and potassium phosphate (6.4 g, 44.9 mmol) in 1 ,4-dioxane (20 ml) was heated at reflux (1000C) under argon for 20 hours. The mixture was allowed to cool to room temperature and then diluted with dichloromethane and 0.88M ammonia diluted in water (1 :5). The mixture was extracted into dichloromethane (x3), and then the combined organic extracts were washed with water (x2) and dried over magnesium sulphate. The solvent was evaporated in vacuo and the crude product was purified by flash-silica gel chromatography, eluting with 5% 2M ammonia in methanol in dichloromethane, to give the product 1-(2-chloro-4-fluorophenyl)-2-piperazinone (250mg) as a brown oil which was used without further purification. LC/MS [M+H]+ = 229.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53459; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, 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 1,4-Diiodobutane

Step (a): Synthesis of 1-(4-amino-phenyl)cyclopentanecarboxylic acid methyl esterSodium hydride (2.8 g, 60% dispersion in mineral oil) was added slowly to an ice-cold solution of (4-nitro-phenyl)-acetic acid methyl ester (6.0 g, 30.7 mmol) in anhydrous DMF (30 mL) under nitrogen atmosphere. After stirring at 0 C. for 20 min, 1,4-diiodobutane (7.86 mL, 61 mmol) was added drop wise under stirring. After complete addition, the reaction mixture was warmed to about 20-35 C. and stirring continued for an additional 3 h. The reaction was stopped by adding water drop wise followed by EtOAc. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The material was purified by chromatography over silica gel to afford a pale yellow viscous liquid that solidified on standing at about 20-35 C. (4.1 g, 54% yield). The solid (3.4 g, 13.6 mmol) was dissolved in anhydrous ethanol and tin (II) chloride dihydrate (13.86 g, 61 mmol) was added slowly under nitrogen atmosphere. Thereafter, the mixture was heated at 90 C. for 3 h. After evaporation of volatiles under reduced pressure the resultant mixture was diluted with ice water, and the solution was adjusted to pH 11 by adding NaOH (aq). The mixture was extracted with EtOAc (3×50 mL) and the combined organic extracts were washed with water, brine, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound as a granular light yellow solid (2.67 g, 88% yield).1H NMR (CDCl3, 300 MHz): delta 7.16 (dd, J=8.4, 1.8 Hz, 2H), 6.63 (dd, J=8.4, 1.8 Hz, 2H), 3.59 (s, 3H), 2.60-2.55 (m, 2H), 1.87-1.67 (m, 6H).LC-MSD (ES+): m/z [220 (M+H)+, 100].

The synthetic route of 1,4-Diiodobutane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144722; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 624-75-9, 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. 624-75-9, name is 2-Iodoacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 5-bromo-2-isopropyl-4-methoxy- phenol from step 4(0.831 g, 34 mmol) and K2C03 (0.562 g, 4.1 mmol) in 17 mE dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60 C. for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in SOmE of H20 and extracted with 1:1 toluene/ethyl acetate, washed with H20 and then with brine. The combined organic layers were dried over Na2504, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2C12) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-aceto- nitrile (0.611 g, 63%) as a while solid.

The chemical industry reduces the impact on the environment during synthesis 2-Iodoacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ford, Anthony P.; McCarthy, Bruce G.; US2015/57299; (2015); A1;,
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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-amino-5-iodobenzoate

methyl 4-amino-4′-propyl-[l,l’-biphenyl]-3-carboxylate (4a) Synthesized using reported procedure with modification (US Patent Application Publication Culshaw et al, Pub. No. US 2008/0293939 Al, Nov 27, 2008). To a round-bottom-flask under nitrogen methyl 2-amino-5-iodobenzoate (1) (831 mg, 3 mmol, 1.0 equiv.), 4- propylphenylboronic acid (541 mg, 3.3 mmol, 1.1 equiv.) and DMF (20 mL) were added, followed by addition of catalyst Pd(dppf)Cl2 (110 mg, 0.15 mmol, 0.05 equiv.) and the mixture were stirred for 15 minutes. 2M Na2CC>3 solution (7.5 mL, 15 mmol, 5.0 equiv.) was added and then the mixture was heated at 80 C for 16 hours. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was filtered and concentrated under reduced pressure. H20 (20 mL) was added to the residue which was extracted with EtOAc (2 x 20 mL). All the organic extracts were combined, dried over NaSC>4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=20:80) on silica gel to afford 4a (418 mg, 51%) as yellow solid. XH NMR (400 MHz, CDCI3) delta 8.11 (s, 1H), 7.53-7.20 (m, 5H), 6.71 (d, J= 8.0 Hz, 1H), 5.74 (s, 2H), 3.88 (s, 3H), 2.60 (t, J= 8.0 Hz, 2H), 1.71-1.61 (m, 2H), 0.96 (t, J = 8.0 Hz, 3H); 1 C NMR (100 MHz, CDCI3) delta 168.56, 149.48, 140.96, 137.74, 132.70, 129.37, 129.23, 128.81, 126.03, 117.13, 110.90, 51.54, 37.61, 24.55, 13.82.

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 77317-55-6.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 156150-67-3, 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 156150-67-3 as follows.

EXAMPLE 42-(2-Chloro-4-iodorhohenylaminoV5.5-dimethyl-8-oxo-5,6J.8-tetrahvdro-4H-thienor2,3- clazepine-S-carboxylic acid ethyl ester; Caesium carbonate (2.77 g, 8.51 mmol) and 2-chloro-4-iodo-l-fluorobenzene (2.18 g, 8.51 mmol) were added to a solution of Intermediate 6 (2.0 g, 7.09 mmol) in DMF (20 mL) and heated at 650C for 18 h. Brine (100 mL) was added to the reaction and the mixture extracted with DCM (3 x 50 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residual DMF was azeotroped with heptane. The crude product was purified by chromatography (silica, 0-30% EtOAc in DCM) to give the title compound as a cream solid (916 mg, 25%). deltaeta (DMSO-d6) 10.60 (IH, s), 8.01 (IH, t, J 5.0 Hz), 7.95 (IH, d, J2.0 Hz), 7.78 (IH, dd, J 8.6, 2.0 Hz), 7.54 (IH, d, J 8.6 Hz), 4.32 (2H, q, J 7.1 Hz), 2.91 (2H, s), 2.85 (2H, d, J 5.2 Hz), 1.33 (3H, t, J 7.1 Hz), 0.99 (6H, s). LCMS (ES+) RT 3.81 minutes, 519 (M+H)+.

According to the analysis of related databases, 156150-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2008/20206; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 2-(4-nitrophenyl)acetate (6 g, 31 mmol) in DMF (100 ml) was cooled to 0 C with an ice bath. NaH (60% in oil) (2.5 g, 63 mmol) was added portion wise. The resulting mixture was allowed to warm to RT and was stirred for 15 min at RT. After 15 min the mixture was cooled again to 0 C and 1,3-diiodopropane (6 ml, 52 mmol) was added drop wise. The resulting mixture was allowed to stir at 0 C for 30 min, and from 0 C to 10 C for 1.5 h. After 1.5 h the solution was cooled to 0 C and water was added. The reaction mixture was extracted 3 times with DCM. The combined organics were concentrated under reduced pressure and the residue was purified by flash chromatography on silica (120 g flash column, 0-20% EtOAc in hexane, 10 CV) to afford methyl 1-(4-nitrophenyl)cyclobutanecarboxylate.

The chemical industry reduces the impact on the environment during synthesis 1,3-Diiodopropane(stabilized with Copper chip). I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; SCIAMMETTA, Nunzio; WHITE, Catherine, M.; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (109 pag.)WO2019/74747; (2019); 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. 5326-47-6, name is 2-Amino-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5326-47-6

The starting material 2-amino-5-iodo benzoic acid (1) (15mmol, 4 . 0g) is added to 15 ml of anhydrous methanol solution, then added to this solution in 3M the mass fraction of the 70% concentrated sulfuric acid. Heating to reflux 6h, then room temperature stirring 12h. After the completion of reaction, reducing pressure and evaporating solvent, then added to the residues in the bottle 100 ml saturated sodium bicarbonate solution, ethyl acetate (3×30 ml) extraction. Obtaining organic layer, saturated salt water (3×20 ml) washing, layered takes organically phase is dried with anhydrous sodium sulfate. Filtering, by reduced pressure evaporation to dry solvent to obtain 2-amino-5-iodo benzoic acid methyl ester (2) crude 3.96g, yield: 94.5%

The synthetic route of 5326-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Liu, Xinyong; Zhan, Peng; Kang, Dongwei; (22 pag.)CN105669653; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com