Category: iodides-buliding-blocks

Synthetic Route of 620621-48-9, 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. 620621-48-9, name is Methyl 2-chloro-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 77 :methyl 2-chloro-5-(3-(diethylamino)pyrrolidin-l-yl)benzoate; Methyl 2-chloro-5-iodobenzoate (1.00 g, 3.37 mmol), cesium carbonate (1.648 g, 5.06 mmol), BINAP (0.105 g, 0.17 mmol), palladium(II) acetate (0.038 g, 0.17 mmol) and 7V,7V-diethylpyrrolidin-3 -amine (0.576 g, 4.05 mmol) were suspended in dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 120 0C for 2 hours in the microwave reactor and cooled to RT. The reaction mixture was filtered through celite before concentrating in vacuo. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% NH3ZMeOH in DCM. The product was isolated but still contained less polar impurities. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3ZMeOH and pure fractions were evaporated to dryness to afford methyl 2- chloro-5-(3-(diethylamino)pyrrolidin-l-yl)benzoate (0.257 g, 24.52 %) as a brown gum. mZz (ESI+) (M+H)+ =311; HPLC tR = 1.16 min. 1H NMR (400.13 MHz, DMSO-d6) delta 0.96 (6H, t), 1.80 – 1.85 (IH, m), 2.11 – 2.17 (IH, m), 2.54 – 2.63 (4H, m), 2.99 (IH, t), 3.15 – 3.22 (2H, m), 3.40 – 3.44 (2H, m), 6.53 – 6.56 (2H, m), 7.16 – 7.18 (IH, m), 7.42 (IH, s), 7.67 (IH, s).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-chloro-5-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AstraZeneca AB; AstraZeneca UK Limited; WO2009/47558; (2009); A1;,
Iodide – Wikipedia,
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Reference of 16355-92-3,Some common heterocyclic compound, 16355-92-3, name is 1,10-Diiododecane, molecular formula is C10H20I2, 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 9 (n=10); (a) 1, 1′-[(Decane-1,10-diyl)dioxy]bis[(11S,11aS)-10-(tert- butylOxyCarbonyl)-8-methoxy-11-(tetrahydro-pyran-2-ylOxy)- 1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5- one] (8h); 1,10-Diiododecane (87.8 mg, 0.22 mmol, 0.5 equiv) was added to the mixture of monomer 7 (0.2 g, 0.44 mmol, 1.0 equiv) and potassium carbonate (0.98 mmol, 2.2 equiv) in dry DMF (30 mL), and the resulting mixture was heated to 90C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (Si02, 50% EtOAc-hexane) to afford the dimerized compound 8h (191 mg, 0.1 8mmol, 82% yield, mixture of diastereomers from THP protecting group) as a solid: [a] 20D = +75 (c = 0.10, CHCl3); 1H NMR (CDCl3, 400 MHz): 5 1.25-1. 59 (m, 76H, 14-H, 15-H, 16-H, Boc, THP), 1. 68-1. 92 (16H, 13-H, THP), 1. 93-2. 20 (m, 16H, 1-H, 2-H), 3.45- 3.75 (m, 16H, 3-H, lla-H, THP), 3.83-4. 14 (m, 24H, 12-H, 7-OMe, THP), 5.02-5. 10 (m, 2H, THP), 5.12-5. 19 (m, 2H, THP), 5.69-5. 77 (d, 2H, 11-H), 5.79-5. 89 (d, 2H, 11-H), 6.49 (s, 2H, 9-H), 6. 86 (s, 2H, 9-H), 7.17 (s, 2H, 6-H), 7.21 (s, 2H, 6-H) ; 13C NMR (CDCl3, 400 MHz): 5 19. 9, 20.4, 23.1, 23.2, 25.2, 25.3, 25.9, 28.1, 28.2, 28. 9,29. 0,29. 1,29. 2,29. 3,29. 5,30. 9,31. 3,46. 3, 55. 9, 56. 2, 60. 0,60. 1, 63.3, 69. 1, 80.9, 81.2, 88.2, 91.2, 95. 8, 100. 2, 111.1, 111.5, 113.4, 114.0, 121.6, 126. 4,141. 0,143. 1,148. 1, 148.4, 155.4, 167.4, 167.6 ; IR (neat): 2937,1703, 1643, 1604, 1513,1450, 1392,1327, 1218,1164, 1022cm~1 ; MS (FAB) m/z (relative intensity) 1057 ( [M + Na] +’, 34), 1035 (M+., 100), 833 (26), 933 (25).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Diiododecane, its application will become more common.

Reference:
Patent; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Iodide – Wikipedia,
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Reference of 696-41-3, 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. 696-41-3, name is 3-Iodobenzaldehyde belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1) 1-(3-Iodo-phenyl)-pent-4-en-1-ol To a stirred solution of 3-iodo-benzaldehyde (3.0 g, 12.93 mmol) in dry THF (45 mL) at -78 C. under nitrogen was added 0.5 M 3-butenyl magnesium bromide in THF (25.86 mL, 12.93 mmol) over 20 min. The reaction was stirred for 0.5 h and allowed to warm to -30 C. over 1 h and then quenched with sat ammonium chloride (20 mL). The reaction was diluted with water (10 mL) and then extracted with ethyl acetate (2*50 mL). The extracts were dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (5% to 10% ethyl acetate/petroleum ether) gave the title compound as a clear oil (3.5 g, 95%) and was used directly in the next step.

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

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
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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. 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 444-29-1

Example 37Preparation of 4-hydroxy-3-methoxy-N-[3-[2-(2-trifluoromethylphenyl)ethynyl]phenyl]phenylacetamide: [73.2] A mixture of N-(3-ethynylphenyl)-4-hydroxy-3-methoxyphenyacetamide (the compound of Example 19) (200 mg), 1-trifluoromethyl-2-iodobenzene (280 mg), copper (I) iodide (19 mg), bis(triphenylphosphine)palladium (II) dichloride (70 mg), triethylamine (1 g) and acetonitrile (3 ml) is heated with stirring at 50°C under argon atmosphere for 18 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0 percent to 100 percent hexane/ethyl acetate) to give the desired compound (120 mg).1H-NMR (300MHz, CDCl3, delta): 3.68 (2H, s), 3.92 (3H, s), 5.65 (1H, s), 6.83 (2H, m), 6.96 (1H, d), 7.11 (1H, s), 7.25-7.35 (2H, m), 7.42 (1H, m), 7.44-7.60 (3H, m), 7.52-7.71 (2H, m).

The synthetic route of 444-29-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Pharmaceutical Co., Ltd.; EP1403235; (2004); A1;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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 103440-52-4, Product Details of 103440-52-4

In a dry Schlenk Tube at RT under nitrogen are successively charged 2-iodo-5- methylbenzoic acid methyl ester (13.765 mmol, 1 eq), Cul (2.753 mmol, 0.2 eq), CsF (27.529 mmol, 2 eq), 2-tributylstannylpyridine (20.647 mmol, 1.5 eq), Pd(PPh3)4 (1.376 mmol, 0.1 eq) and DMF (60 ml_). The resulting suspension is stirred at 90C overnight. The obtained reaction mixture is diluted with EtOAc and filtered through a short pad of Celite. A solution of sat. aq. NaHC03 is then added to the filtrate and the aq. phase extracted with EtOAc (3 times). The combined organic layers are washed with H20 and brine, dried over Na2S04, filtered and concentrated under reduced pressure. Purification is achieved by FC (EtOAc/Heptane 1 :4 to 3:7) to give methyl 5-methyl-2-(pyridin-2-yl)benzoate (2.64 g) as a brown oil. LC-MS (conditions A): tR = 0.67 min, [M + 1 ]+ = 228.07.

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Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BROTSCHI, Christine; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi T.; WO2012/85857; (2012); A1;,
Iodide – Wikipedia,
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16355-92-3, name is 1,10-Diiododecane, 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. Safety of 1,10-Diiododecane

5.(1) Synthesis of 10-iododecyl allyl ether 52 mmol (3.0 g) of allyl alcohol was dissolved in 50 ml of THF. Into the solution added gradually was 2.3 g of 60% sodium hydride. After the mixture had been stirred for 10 minutes at room temperature, a solution consisting of 127 mmol (50.0 g) of 1,10-diiododecane and 100 ml of THF was added into the mixture dropwise. After conclusion of dropping, the resulting mixture was refluxed for 12 hours. A small amount of water was then added to the reaction solution, to decompose the residual sodium hydride. After THF had been distilled out under reduced pressure, water and dichloromethane were added to the residue, and the mixture was then shaken. The dichloromethane layer was collected and was dried over magnesium sulfate. The dried dichloromethane layer was concentrated under reduced pressure, and the residue was purified by column chromatography, to obtain 13.1 g of the objective omega-haloalkyl allyl ether (Yield: 78%).

The synthetic route of 16355-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; US5243065; (1993); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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 148870-57-9, Application In Synthesis of 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one

To a mixture of (S)-N-[(4,5-dimethoxybenzocyclobut-l-yl)-methyl]-N-(methyl)amine (42g) and N,N-dimethylformamide (220ml) was charged 7,8-dimethoxy-3-[3-iodopropyl]-l,3-dihydro-2H- 3-benzazepin-2-one (75g) and potassium carbonate (42g) at room temperature. The reaction mixture was heated and stirred the reaction mass at 50-55 C for 2 hours and the completion of reaction was monitored by HPLC/TLC. After completion of reaction, reaction mass was cooled to 25-30 C and diluted with dimineralized water (1000ml). The reaction mixture was extracted with methylene dichloride (400ml x 200ml) and the layers were separated. Methylene chloride was distilled off completely. To the residue, dimineralized water (200ml) and hydrochloric acid (50ml) were added and the aqueous solution is washed with ethyl acetate (200ml x 3). The layers were separated and to the aqueous layer 50 % (w/v) sodium hydroxide solution (120ml) was added at 25-30 C. The aqueous layer was extracted with ethyl acetate (400ml + 200 ml) and the combined ethyl acetate layer was washed with 5 %( w/v) sodium hydroxide solution (300ml). Ethyl acetate layer was dried over anhydrous sodium sulfate and then ethyl acetate was distilled out completely under vacuum to get the title compound.

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; IND-SWIFT LABORATORIES LIMITED; WO2008/146308; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52807-27-9, A common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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.

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 52807-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 7681-82-5, name is Sodium iodide, molecular formula is INa, 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. Quality Control of Sodium iodide

General procedure: All reagents were ACS-reagent grade. Distilled water was used for the preparation of solutions. The procedure for the preparation of CaApOH is as follows: samples of 1.2g Ca(NO3)2·4H2O, 0.5g Na3PO4, and 0.04g NaOH were placed in the bottom of a 125mL Erlenmeyer flask equipped with a standard taper joint bearing a condenser with a thermometer inserted in the condenser and held slightly above the bottom of the flask (but in the solution) by a thin slice of suction tubing at the top of the condenser. The flask was placed on a heating/stir plate and 50mL of distilled water was added. The solution was stirred magnetically and heated to 80C for approximately 3h. The pH was measured, but not adjusted, at the beginning and at the end of the 3h of digestion using Hydrion pH 1.0-12.0 paper. [In order to determine the effect of pH, the pH was adjusted with 3 M NaOH for some samples at the beginning and during digestion.] Stirring was then discontinued and the solution was allowed to cool and settle overnight. The precipitate was suction filtered in a medium porosity glass filter crucible and washed 5 times with a total of about 150mL of distilled water. The precipitate was dried in a vacuum drying oven at 110 C for at least 4h and then ground with a mortar and pestle and stored in a closed, parafilmed vial.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7681-82-5, its application will become more common.

Reference:
Article; Yoder, Claude H.; Havlusch, Maxwell D.; Dudrick, Robyn N.; Schermerhorn, Janse T.; Tran, Linh K.; Deymier, Alix C.; Polyhedron; vol. 127; (2017); p. 403 – 409;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, 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. name: 4-Iodo-2-methylaniline

General procedure: Aniline derivative (1 eq) was mixed with iced water and/or absolute EtOH (2 mL by mmol of reagent) and stirred at 0 C then hydrochloric acid 37% (4 eq) was added dropwise rapidly. Sodium nitrite (1.1 eq or 1.3 eq aniline substituent depending) was added solid or in solution (H2O/EtOH 1 M) and the reaction mixture was stirred at 0-2 C for 30 min. The solvent was removed carefully under reduced pressure without heating and can be used without further purification. 5-Amino-4-hydroxynaphtalene-2,7-disulfonic acid sodium salt (0.9 eq) was dissolved in iced water (5 mL by mmol of reagent) then pH was adjusted to 9 by adding 30% NaOH solution. The diazonium salt was added to the naphthalene moiety and pH maintained at 9 by addition of 10% NaOH solution. After complete addition of the diazonium salt to the 5-amino-4-hydroxynaphthalene-2,7-disulfonic acid monosodium salt, stirring was maintained at 0 C for 2 h. Degraded diazonium was removed after extraction with EtOAc and water soluble diazo compounds were recrystallized three times from EtOH/(H2O; pH 2) (1/1). All organic impurities were then extracted by washing with small portions of Et2O. The precipitated compounds were dried under vacuum.

The synthetic route of 4-Iodo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Favre-Besse, Franck-Cyril; Poirel, Odile; Bersot, Tiphaine; Kim-Grellier, Elodie; Daumas, Stephanie; El Mestikawy, Salah; Acher, Francine C.; Pietrancosta, Nicolas; European Journal of Medicinal Chemistry; vol. 78; (2014); p. 236 – 247;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com