Category: iodides-buliding-blocks

Application of 173406-17-2, 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. 173406-17-2, name is tert-Butyl 3-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 8B; tert-Butyl 3-[N-(3-Chloro-4-methoxyphenyl)-pyridin-3-ylmethylamino] benzoate; To a solution of 3-chloro-4-methoxyphenyl-N- (3-pyridylmethyl) amine (248 mg, 1 mmol) and t- butyl 3-iodobenzoate (450 mg, 1.5 mmol) in 10 mL toluene was added NaOtBu (150 mg, 1.5 mmol), Pd2dba3 (18 mg, 0.02 mmol), and P (tBu) 3HBF4 (12 mg, 0.04 mmol). The mixture was stirred overnight then filtered through celite and loaded onto a silica column (12g). The product was eluted with a linear gradient from 30% to 45% EtOAc in hexanes to give tert-Butyl 3-[N-(3- Chloro-4-methoxyphenyl)-pyridin-3-ylmethylamino] benzoate as a yellow oil.

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

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/61458; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13421-13-1, name is 4-Chloro-2-iodobenzoic acid, 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 13421-13-1, Recommanded Product: 13421-13-1

4-chloro-2-iodobenzoic acid 7a (15 g, 53 mmol) was dissolved in dry THF (250 mL) and the solution was cooled to 0 C. Hereupon, NEt3 (1 1 mL, 80 mmol) and ethyl chloroformate (7.6 mL, 80 mmol) were added. The reaction was stirred for 1.5 hour and subsequently NaBH (8.0 g, 210 mmol) was added in four portions. After 1.5 hour, additional NaBH (4.0 g, 105 mmol) was added and the reaction was stirred for another hour. Hereupon, the reaction was quenched with H20 (100 mL) and EtOAc (200 mL) was added. The organic layer was washed with H20 (3 chi 150 mL), brine (100 mL) and subsequently dried over MgS04. The solvents were removed under reduced pressure and the crude product was obtained by gradient column chromatography (EtOAc/-heptane, 1 :9 to 1 :6). Compound 8a was obtained as white solid (8.4 g, 75% over 2 steps). 1H-NMR (400 MHz, CDC13) delta: 7.82 (s, 1H), 7.45-7.33 (m, 2H), 4.65 (d, J = 6.2 Hz, 2H), 1.94 (t, J = 6.2 Hz, 1H). 13C- NMR (75 MHz, CDC13) delta: 141.1, 138.3, 133.8, 128.8, 128.6, 96.9, 68.6. HRMS (EI+) m/z calcd for C7H60C1I [M]’+ 267.9152, found 267.9160.

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

Reference:
Patent; STICHTING KATHOLIEKE UNIVERSITEIT; SYNAFFIX B.V.; DEBETS, Marjoke Froukje; RUTJES, Floris Petrus Johannes Theodorus; VAN HEST, Jan Cornelis Maria; VAN DELFT, Floris Louis; VAN BERKEL, Sander Sebastiaan; WO2014/189370; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 7681-82-5, 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. 7681-82-5, name is Sodium iodide, This compound has unique chemical properties. The synthetic route is as follows.

PdCl2 (PPh3) 2 (50 mg, 0.071 mmol),NaI (107 mg, 0.71 mmol),10 mL of dichloromethane,And 10 mL of water were sequentially added to a 50 mL round bottom flask,The reaction was stirred at room temperature for 8 hours and the organic layer was separated,Dried over anhydrous sodium sulfate,Filter concentrate,The crude product was recrystallized from dichloromethane / petroleum ether to give red crystals as PdI2 (PPH3) 2 complex,Yield: 90%.

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

Reference:
Patent; Tianjin Normal University; Liu, Guiyan; Liu, Chengxin; (7 pag.)CN106243151; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 626-62-0, These common heterocyclic compound, 626-62-0, name is Iodocyclohexane, 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: THF (1.5 mL), organic halide 3 (1.5 mmol, 1.0 equiv) and Ir(dtbbpy)(ppy)2 PF6 (3.5 mg, 0.0025 equiv) were successively added to a test tube containing Zn dust (73 mg, 1.125 mmol, 0.75 equiv). The reaction mixture was stirred under irradiation with a strip of 400 nm LEDs for 5 h, with water cooling to maintain the reaction temperature around 23-25 C. For the work-up, H2O (5 mL) was added and the mixture was extracted with hexane (3 ¡Á 7 mL). The combined extracts were filtered through Na2SO4 and concentrated under vacuum.The residue was purified by flash chromatography eluting with hexane/EtOAc.

The synthetic route of 626-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Levin, Vitalij V.; Agababyan, Daniil P.; Struchkova, Marina I.; Dilman, Alexander D.; Synthesis; vol. 50; 15; (2018); p. 2930 – 2935;,
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. 25245-27-6, name is 1-Iodo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H9IO2

To a solution of aryl methoxy substituted aryl iodide (40 mmol) in isopropylamine (250 ml) were added Pd(PPh3)2Cl2 (0.4 mmol) and CuI (0.8 mmol), then trimethylsilylacetylene (44 mmol). The reaction mixture was stirred at ambient temperature for 2 to 4 hours under a slow stream of nitrogen. The reaction mixture was filtered and the residues were washed with ethyl acetate, and the solvent evaporated from the combined filtrates. The crude product was purified by column chromatography on silica gel using petroleum/ethyl acetate as an eluent to give the methoxy substituted arylethylyl trimethylsilanes.

According to the analysis of related databases, 25245-27-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KENT STATE UNIVERSITY; SUMMA HEALTH SYSTEM; WO2008/157745; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic 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. Recommanded Product: 391211-97-5

To a flask containing 3, 4-difluoro-2- (2-fluoro-4-iodo-phenylamino)-benzoic acid (2.6 Kg, 6.6 mol) and N, N’-carbonyldiimidazole (1.1 Kg, 6.8 mol) under nitrogen atmosphere, was added 12 L of dry acetonitrile. After stirring at 22 5C for about 90 minutes, a solution of (R)-O- (2, 2-dimethyl- [1, 3] dioxolan-4-ylmethyl)-hydroxylamine in toluene was added (8.5 L total volume, about 8 moles of amine). The solution was stirred for at least 6 hours at 22 5 C. Aqueous hydrochloric acid (9 L, 1.5 molar) was added, and after stirring for about 5 minutes, the layers were separated. Aqueous hydrochloric acid (9 L, 1.5 molar) was added to the remaining top layer, and after stirring for about 20 hours, the layers were separated. The remaining top layer was concentrated by vacuum distillation, and then diluted with 15 L toluene and 2 L ethanol. The mixture was warmed to 35-45C and diluted with 20 L warm water, then cooled to 0-5C. The product was collected by filtration and washed with 2 L toluene. The product was recrystallized by dissolving in 12 L toluene and 2 L ethanol (50 5 C), adding 10 L water and cooling to 0-5C. After collecting the product by filtration and washing with toluene, the product was dried in a vacuum oven resulting in 2.6 Kg of N-[(R)- 2,3-Dihydroxypropoxy]-3, 4-difluoro-2- (2-fluoro-4-iodo-phenylamino)-benzamide. 2.4 Kg of the above compound as a mixture of different crystalline forms was stirred in a mixture of 10 L water and 1 L ethanol at 35+ 5C for 20-30 hours, then cooled to 25+ 5C. The product was collected by filtration and washed with 1 L of water, then dried in a vacuum oven at 65C. This resulted in 2.3 Kg of material which was greater than 90% form IV. Note: DSC analysis shows an onset of melting at 110C with only a small amount of the peak with an onset of melting at 117C.

The synthetic route of 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/46665; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-55-7,Some common heterocyclic compound, 103440-55-7, name is Methyl 2-iodo-6-methylbenzoate, molecular formula is C9H9IO2, 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.

Methyl 2-iodo-6-methylbenzoate (158) (2.00 g, 7.245 mmol) and NBS (1.418 g, 7.969 mmol) were stirred in chlorobenzene (50 mL) and benzoyl peroxide (75% w/w, 0.234 g, 0.724 mmol) was added. The reaction was stirred at 90 C for 18 hours, cooled to room temperature, filtered and the precipitate was washed with cyclohexane (4×10 mL). The combined filtrates were evaporated, and the resulting brown oil was diluted with THF (50 mL). Aqueous ammonia solution (20 mL) was added, and the mixture was stirred vigorously for 1 hours. The mixture was diluted with water (20 mL) and the THF was removed in vacuo. DCM (150 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (2x 00 mL), the combined organics were washed with brine (100 mL), dried (MgS04) and filtered. Silica gel was added and the volatiles were removed in vacuo to give the crude material absorbed onto silica gel. The material was purified by silica gel chromatography (Biotage Isolera, 40 g Si cartridge, 0-100% EtOAc in petroleum benzine 40-60 “C, then 0-20% methanol in EtOAc) to give the title compound (159) (0.757 g, 40% yield) as a beige solid; 1H NMR (400 MHz, CDCI3) delta 7.93 (dd, J = 7.8, 0.7 Hz, 1 H), 7.46 (dd, J = 7.5, 0.8 Hz, 1 H), 7.26 – 7.21 (m, 1 H), 7.10 (br s, 1 H), 4.37 (d, J = 0.6 Hz, 2H). LCMS Method C: rt 5.06 min; m/z 260.0 IM+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-iodo-6-methylbenzoate, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 144550-76-5, 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. 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

C. 4-Iodo-2-(Quinoxaline-5-sulfonylamino)benzoic acid methyl ester. A solution of methyl 2-amino-4-iodobenzoate (1.2 g, 4.4 mmol), quinoxaline-5-sulfonyl chloride (1.2 g, 5.3 mmol), pyridine (1.7 mL, 22 mmol) and DCM (25 mL) was maintained at 23 C. for 24 h. The reaction mixture was diluted with DCM (200 mL) and washed with satd. aq. NaHCO3, then dried and concentrated to a tan solid. This residue was chromatographed (0 to 100% EtOAc/CH2Cl2) to afford the sulfonamide as a light yellow solid (1.6 g, 77%). MS (ESI): calculated for C16H12IN3O4S, 469.0; m/z found, 470 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 11.10 (s, 1H), 9.07 (d, J=1.8 Hz, 1H), 9.01 (d, J=1.8 Hz, 1H), 8.60 (dd, J=7.4, 1.3 Hz, 1H), 8.40 (dd, J=8.5, 1.3 Hz, 1H), 8.04 (dd, J=7.5, 1.0 Hz, 1H), 7.99 (d, J=1.6 Hz, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.37 (dd, J=8.3, 1.6 Hz, 1H), 3.88 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-4-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Allison, Brett D.; Hack, Michael D.; Phuong, Victor K.; Rabinowitz, Michael H.; Rosen, Mark D.; US2005/38032; (2005); 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. 116632-39-4, name is 5-Bromo-2-iodotoluene, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-2-iodotoluene

In dioxane (5 mL) solution of tert-butyl 5-hydroxy-4-methyl-2,3-dihydro-1H-indole-1-carboxylate (250 mg) and 5-bromo-2-iodo toluene (212 muL), copper iodide (I) (38.1 mg), N,N-dimethyl glycine (41.2 mg), cesium carbonate (651 mg) was added and stirred for 24 hours at 100 C. The reaction mixture into a saturated ammonium chloride solution (6 mL), saturated aqueous sodium bicarbonate (3 mL), and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After washing the resulting residue with hexane, collected by filtration, and dried to give the title compound (57.5 mg) as a white solid.

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 116632-39-4.

Reference:
Patent; DAIICHI SANKYO COMPANY LIMITED; NAGAMOCHI, MASATOSHI; GOTANDA, KENTOKU; NOGUCHI, TETSUJI; GOTO, TAIJI; SASAKI, JUNKO; TORIHATA, MUNEFUMI; YOSHINO, TOSHIHARU; ISOBE, TAKASHI; (97 pag.)JP2016/108257; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-52-4,Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, molecular formula is C9H9IO2, 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: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (10 mg, 0.05 mmol, 10 mol%), K2CO3 (276 mg, 2.0 mmol), 1,10-phenanthroline (20 mg, 0.10 mmol, 20 mol%) and cyclic thiourea (0.5 mmol), 4 ? Molecular Sieves. The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, methyl-2-iodobenzoate 1 (0.6 mmol) and DMF (2.0 mL) were added by syringe. The mixture was stirred at 100 oC for 24h. After the reaction was completed, the mixture was directly passed through celite and rinsed with 30 mL of EtOAc. The combined filtrate was concentrated and purified by column chromatography on silica gel to give the pure product.Yellow Yellow solid; mp 105-107 C; 1H NMR (400 MHz, CDCl3) delta 8.09 (s, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 3.73 (s, 2H), 3.30(s, 2H), 2.40 (s, 3H), 1.07 (s, 6H); 13C NMR (100 MHz, CDCl3) delta 161.6, 136.5, 134.6, 131.2, 129.7, 124.1, 122.0, 57.0, 52.5, 27.9, 24.2, 20.8 ppm. Anal. Calcd. for C14H16N2OS: C 64.58, H 6.19, N 10.76; found: C 64.25, H 6.27, N 10.49; EI-MS: m/z = 260 (M+)

The synthetic route of 103440-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Dingben; Wu, Jiashou; Yang, Jianguo; Huang, Ling; Xiang, Yubo; Bao, Weiliang; Tetrahedron Letters; vol. 53; 52; (2012); p. 7104 – 7107;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com