Category: iodides-buliding-blocks

2401-21-0, The chemical industry reduces the impact on the environment during synthesis 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, I believe this compound will play a more active role in future production and life.

Example 93 (S)-2-({1-[(E)-3-(2, 3-DICHLORO-PHENYL)-BUT-2-ENOYL]- PIPERIDINE-4-CARBONYL}-AMINO)-PROPIONIC acid Example 93A (E)-3- (2, 3-Dichloro-phenyl) -but-2-enoic acid ethyl ester A stirred solution of 2,3-dichloroiodoben- zene (3.00 g, 11.0 mmol) in dimethyl acetamide (10 ML) was heated to 100¡ãC for 16 h with tetrabutyl- ammonium chloride (2.78 g, 10.0 mmol), palladium acetate (90 mg, 0.40 mmol), dicyclohexyl methylamine (2.93, 15.0 mmol), and ethyl crotonate (1.41 g, 10.0 mmol) under N2 [procedure taken from Buchwald (1995) Chem. Eur. J 5: 3107-3112]. The reaction was diluted with methylene chloride (30 mL), and washed with 1N aqueous HC1 (3X20 mL) and water (3X20 mL). The organic phase was dried (NA2SO4), filtered, and concentrated to obtain an orange oil. The crude product was purified on a Biotage Flash 40 chroma- tography system eluting with the following gradient: 3percent methyl tert-butyl ether in petroleum ether (1 L) then 5percent methyl tert-butyl ether in petroleum ether (500 mL). Example 93A (500 mg, 19percent) was obtained as a white powder. 1H NMR (CDC13, 400 MHz) 5 7.42 (dd, J=8.20, 1.56 Hz, 1H), 7.19 (m, 1H), 7.08 (dd, J=7.81, 1.56 Hz, 1H), 5.81 (m, 1H), 4.22 (q, J=7.16 Hz, 2H), 2.47 (d, J=1.56 Hz, 3H), 1.32 (t, J=7.22 Hz, 3H). Based ON 1H NMR analysis, Example 93A had the”E”olefin geometry (see, Dyker (1999) Helv. Chim. Acta 82 : 588-596, for NMR data of an analogous o-bromo analogue).

The chemical industry reduces the impact on the environment during synthesis 1,2-Dichloro-3-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ICOS CORPORATION; WO2005/16883; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 1878-69-9, name is 2-(3-Iodophenyl)acetic acid, I believe this compound will play a more active role in future production and life. 1878-69-9

A solution of 2-(3-iodophenyl)acetic acid (1.05 g, 4.0 mmol, commercially available) in EtOH (12 mL) was treated with 2 drops of concentrated sulfuric acid. The resultant solution was heated at reflux for 90 min, cooled to RT and poured into hexanes (50 mL) and EtOAc (50 mL). The organics were with saturated Na2CO3 (2×50 mL), H2O (50 mL), brine(50 mL), dried (MgSO4) and concentrated to yield ethyl 2-(3-iodophenyl)acetate (1.11 g, 95% yield).

The chemical industry reduces the impact on the environment during synthesis 1878-69-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, A new synthetic method of this compound is introduced below.

2-Amino-5-iodo-benzoic acid methyl ester (14.00 g) was dissolved in dry THF (50 mL) and 1 M diisobutylaluminium hydride in THF (165 mL) was added dropwise to this solution at -300C. The solution was then stirred at -15C for 1 h. To this mixture MeOH (50 mL) was added portionwise, maintaining the temperature of the solution below -5C. The resulting mixture was then left at -15C for 18 h. The formed solid was filtered off and washed with MeOH. The organic phase was dried and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 1-5% methanol in dichloromethane) to give the title compound (9.70 g); ESMS m/z 249.9 [M+H]

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; GLAXO GROUP LIMITED; GLAXOSMITHKLINE ISTRAZIVACKI CENTAR ZAGREB D.O.O.; WO2007/54296; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1643-29-4, name is 3-(4-Iodophenyl)propanoic acid, 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. 1643-29-4

To a stirred solution of 3-(4-iodophenyl)propanoic acid (commercially available) in toluene and methanol (9:1, 0.2 M) 0 C. was added (diazomethyl)trimethylsilane (1 N solution in Et2O, 2 eq). After stirring at room temperature overnight the reaction mixture was concentrated under vacuum and the resulting crude residue was purified by chromatography (silica gel, 20-50% EtOAc in hexanes) to afford methyl 3-(4-iodophenyl)propanoate.

Statistics shows that 1643-29-4 is playing an increasingly important role. we look forward to future research findings about 3-(4-Iodophenyl)propanoic acid.

Reference:
Patent; GlaxoSmithKline Biologicals SA; Skibinski, David; Jain, Siddhartha; Singh, Manmohan; O’Hagan, Derek; (124 pag.)US9408907; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

461-17-6, These common heterocyclic compound, 461-17-6, name is 1,1,1-Trifluoro-4-iodobutane, 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 the byproduct from Example 11, Cs2CO3, 4,4,4-trifluorobutyl iodide and DMF was stirred at room temperature for 3 days. Aqueous work up gave the title compound 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 461-17-6.

Reference:
Patent; Nadin, Alan John; Owens, Andrew Pate; Teall, Martin Richard; US2005/75320; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

628-21-7, The chemical industry reduces the impact on the environment during synthesis 628-21-7, name is 1,4-Diiodobutane, I believe this compound will play a more active role in future production and life.

Sodium hydride (2.8 g, 60% dispersion in mineral oil) was added slowly to a solution of (4-nitro-phenyl)-acetic acid methyl ester (6.0 g, 30.7 mmol) in anhydrous DMF (30 mL) under nitrogen at a temperature in the range of 0 C. to 10 C. After stirring at a temperature in the range of 0 C. to 10 C. for 20 min, diiodobutane (7.86 mL, 61 mmol) was added drop-wise under stirring. After complete addition, the reaction mixture was warmed to a temperature in the range of 15 C. to 40 C. and stirring continued for an additional 3 hours. The reaction was quenched by adding water slowly. The mixture was extracted by ethyl acetate (3¡Á40 mL). The combined organic extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resultant gummy material was purified by column chromatography over silica gel to afford a pale yellow thick liquid which solidified on standing at a temperature in the range of 15 C. to 40 C. (4.1 g, 54% yield). The solid (3.4 g, 13.6 mmol) was dissolved in anhydrous EtOH and tin chloride dihydrate (13.86 g, 61 mmol) was added slowly under nitrogen. Thereafter, the mixture was heated at 90 C. for 3 hours. After evaporation of volatiles under reduced pressure, the resultant mixture was diluted with ice-water and aqueous sodium hydroxide was added to adjust pH 11. The mixture was extracted with ethyl acetate (3¡Á50 mL). The combined organic extracts were washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a granular light yellow solid (2.67 g, 88% yield).1HNMR (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 chemical industry reduces the impact on the environment during synthesis 628-21-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3032-81-3, A common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, molecular formula is C6H3Cl2I, 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.

3,5-dichloro-iodo-benzene (5g, 18 mmol) was stirred at room temperature as a solution in DMF (50 ml.) containing tert butyl acrylate (6.5 mL, 2.5 eq), tetrabutyl ammonium chloride hydrate (5.1 g, 1 eq), potassium acetate (5.4 g, 3 eq) and palladium (II) acetate (~200mg, 30 molpercent) for 5 hours. Reaction mixture was reduced in vacuo, partitioned between water and ethyl acetate. Ethyl acetate fractions were dried over magnesium sulfate, filtered over a small plug of silica gel. Silica gel plug washed with 10 percent Ethyl aceated / n-heptanes to afford 3-(3,5-Dichloro-phenyl)-acrylic acid tert butyl ester after evaporation as a white solid. 1H NMR (400 MHz, DMSO-D6) delta ppm 1.46 (s, 9 H) 6.69 (d, J=16.04 Hz, 1 H) 7.49 (d, J=16.04 Hz, 1 H) 7.59 (t, J=1.89 Hz, 1 H) 7.81 (d, J=1.77 Hz, 2 H).

The synthetic route of 3032-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/40410; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, The chemical industry reduces the impact on the environment during synthesis 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, I believe this compound will play a more active role in future production and life.

5-Iodoanthranilic acid methyl ester (1 g, 3.61 mmol) and formamide (2 ml) were used as a reactant and solvent, then the reaction was carried out in a microwave reactor for 1 hour at 200 C in a microwave reactor vial. After the completion of the reaction, the resulting solid compound was washed with water and then the water was removed from the oven at 100 C for about 1 hour to obtain Compound 1 (784 mg, 2.88 mmol, 80%).

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

Reference:
Patent; Chung Ang University industry Academic Cooperation Foundation; Min, Kyung-Hoon; Lee, Seul; (24 pag.)KR2017/15848; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 20691-72-9 as follows. 20691-72-9

Method c: To a solution of the 4-iodo-2-nitroaniline (550 mmol) and DMAP (1.22 g, 10 mmol) in THF (1000 mL) at 23 C. was dropwise added within 70 min a solution of Boc2O (246 g, 1128 mmol) in THF (500 mL) and stirring was continued at 23 C. for 75 min. The entire mixture was evaporated to dryness and dried at HV to leave a dark brown solid (253.59 g). This material was dissolved in DCM (1100 mL), cooled to 0 C. and TFA (84 mL, 1100 mmol) was added dropwise. The mixture was stirred at 0 C. for 2 h, poured into icecold sat. NaHCO3-sol., extracted with DCM, washed with brine and dried over MgSO4. Removal of the solvent in vacuum left a dark brown solid (199.71 g) which was coated on silica gel and purified by silica gel column chromatography with hexane/EtOAc to give the (4-iodo-2-nitro-phenyl)-carbamic acid tert.-butyl ester as a yellow solid.

According to the analysis of related databases, 20691-72-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-la Roche Inc.; US6407094; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

83863-33-6, 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. 83863-33-6, name is 5-Iodo-2-methylaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Referential Example 9 2.1 mL of benzoyl chloride was added to 70 mL of a methylene chloride solution containing 3.5 g of 5-iodo-2-methylaniline and 2.5 mL of triethylamine at room temperature and stirred at the same temperature for 30 minutes. 1.0 mol/L hydrochloric acid was added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution, and the solvent was evaporated under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue and a solid substance was separated by filtration to obtain 4.2 g of N-(5-iodo-2-methylphenyl)benzamide as pale yellow solid. 1H-NMR (CDCl3) delta: 2.29 (3H, s), 6.96 (1H, d, J = 8.0 Hz), 7.44 (1H, dd, J = 1.6, 8.0 Hz), 7.49-7.63 (4H, m), 7.86-7.88 (2H, m), 8.39 (1H, d, J = 1.6 Hz).

The synthetic route of 83863-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1820795; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com