Tag: M.W=200-300

5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, 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. Product Details of 5460-32-2

To a solution of the appropriate 4-iodobenzene 7a,b (1.0 mmol)in DMF (10 mL) were added the following reagents through thereferred order: acrolein diethyl acetal (0.46 mL, 3.0 mmol), nBu4-NOAc (0.603 g, 2.0 mmol), K2CO3 (0.207 g, 1.5 mmol), and Pd(OAc)2 (6.7 mg, 0.03 mmol) (for 8a) or PdCl2 (5.3 mg, 0.03 mmol) (for 8b). This mixturewas stirred at 90 ¡ãC for 4 h for 8a and 21 h for 8b. After this period, it was poured onto ice (50 g) and H2O (100 mL) and thepH was adjusted to 1 with diluted HCl. In the case of 8a, this aqueous solution was extracted with Et2O (3 50 mL) and theorganic layer was dried over anhydrous Na2SO4. In the case of 8b, the obtained precipitate was filtered off, taken in CH2Cl2 and driedover anhydrous Na2SO4. The solvent was evaporated to the dryness and both residues were purified by silica gel column chromatographyusing CH2Cl2 as eluent.4.1.7.1. (E)-3,4-Dimethoxycinnamaldehyde (8a). White solid(102 mg, 53percent yield); Rf 0.28. Mp 80-82 ¡ãC. 1H NMR (300.13 MHz,CDCl3): delta 9.66 (d, J 7.8 Hz, 1H, CHO), 7.42 (d, J 15.8 Hz, 1H, H-b), 7.17(dd, J 8.3 and 2.0 Hz, 1H, H-6), 7.08 (d, J 2.0 Hz, 1H, H-2), 6.91 (d, J8.3 Hz, 1H, H-5), 6.62 (dd, J 15.8 and 7.8 Hz, 1H, H-a), 3.94 (s, 3H, 4-OCH3), 3.93 (s, 3H, 3-OCH3) ppm. 13C NMR (75.47 MHz, CDCl3):delta 193.5 (CHO), 152.8 (C-b), 151.9 (C-4), 149.3 (C-3), 126.9 (C-1), 126.6(C-a), 123.3 (C-6), 111.0 (C-5), 109.7 (C-2), 55.9 and 55.8 (3,4-OCH3)ppm. ESI-MS m/z (percent): 215 ([M+Na]+, 100), 193 ([M+H]+, 95). ESIHRMSm/z calcd for [C11H12O3H]: 193.0865, found: 193.0855.

The synthetic route of 5460-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sousa, Joana L.C.; Proenca, Carina; Freitas, Marisa; Fernandes, Eduarda; Silva, Artur M.S.; European Journal of Medicinal Chemistry; vol. 119; (2016); p. 250 – 259;,
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Some common heterocyclic compound, 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, molecular formula is C8H8INO2, 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 Methyl 4-amino-3-iodobenzoate

General procedure: To a solution of vinyl bromide a-c (6.7 mmol) in dioxane (30 mL) at 25 C under argon were successively added Et3N (3.70 mL, 26.9 mmol), Pd (PPh3)4 (779 mg, 0.670 mmol), and pinacolborane (2.90 mL, 20.2 mmol) dropwise. The solution was heated to 80 C for 1 h. After cooling, water (5 mL) was added dropwise followed by methyl 4-amino-3-iodobenzoate (1.5 g, 5.4 mmol) dissolved in dioxane (15 mL) and Ba(OH)2¡¤8H2O (6.40 g, 20.2 mmol). The solution was heated to 90 C for 8 h. After cooling, the mixture was filtered through Celite, brine was added (40 mL), and the solution was extracted with ethyl acetate (3 ¡Á 50 mL). After drying over magnesium sulfate and evaporation of the solvents under vacuum, the residue was purified by flash chromatography to obtain the benzoates.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19718-49-1, its application will become more common.

Reference:
Article; Li, Yanwu; Silamkoti, Arundutt; Kolavi, Gundurao; Mou, Liyuan; Gulati, Shelly; Air, Gillian M.; Brouillette, Wayne J.; Bioorganic and Medicinal Chemistry; vol. 20; 14; (2012); p. 4582 – 4589;,
Iodide – Wikipedia,
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Related Products of 364-75-0, 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 364-75-0 as follows.

A solution of the compound of Example 1(e) (4.6 g, 17.54 mmol), 1-fluoro-4-iodo-2-nitrobenzene of Intermediate Example 3 (4.683 g, 17.54 mmol, 1.0 eq.) and potassium fluoride (1.22 g, 21.05 mmol, 1.2 eq.) in DMF was heated at 130 C. for 5 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off and the crude residue was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane) to give the product in 76% yield (6.8 g). 1H NMR (300 MHz, DMSO-d6): delta 10.15 (br s, 1H), 9.41 (s, 1H), 8.35 (d, 1H), 7.78 (dd, 1H), 7.66-7.54 (m, 3H), 7.39 (m, 1H), 7.22 (m, 1H), 7.14-7.11 (m, 2H), 2.06 (s, 3H).

According to the analysis of related databases, 364-75-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (2015); A1;,
Iodide – Wikipedia,
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Application of 116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-bromo-1-iodo-2-methylbenzene (240 muL, 1.68 mmol, Aldrich), Copper(I) iodide (353 mg, 1.85 mmol, Alfa Aesar), Methanesulfinic acid, sodium salt (688 mg, 6.74 mmol, Alfa Aesar) and DMSO (7.2 mL) was purged with Argon and then heated under microwave condition at 125 C. for 20 min. The resulting mixture was stirred at 100 C. for 3 h and then cooled to room temperature. The reaction mixture was diluted with H2O and extracted with EtOAc (2¡Á). The organic layers were combined and washed with brine, dried over Na2SO4 and concentrated in vacuo to a white solid. The solid was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes) to yield 270 mg of desired product as a white solid. MS (ESI) 249 (M+H).

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, 5-Bromo-2-iodotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/23702; (2009); 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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3ClFI

INT 18 2-Chloro-6-fluoro-3-iodobenzonitrile Step A: 2-Chloro-6-fluoro-3-iodobenzaldehyde A solution of diisopropylamine (870 mg, 8.6 mmol) in anhydrous THF was added n-butyllithium (2.5 M in hexanes, 3.1 mL, 7.8 mmol) dropwise over 5 min under nitrogen at 0 C. After 10 min, the reaction mixture was cooled to -78 C and 2-chloro-4-fluoro-l-iodobenzene (2.0 g, 7.8 mmol) was added dropwise over 5 min. After 1 h at – 78 C, DMF (640 mg, 8.6 mmol) was added dropwise over 5 min. After a further 10 min at -78 C, the reaction mixture was quenched by the rapid addition of acetic acid (2.0 mL), followed quickly by water (50 mL). The cold solution was extracted with diethyl ether and the organic extracts were washed with diluted HCl (0.2 M, 25 mL), water, brine and dried over anhydrous sodium sulfate. The solvent was removed under reduce pressure and the resulting residue was then purified by silica gel chromatography to provide 2-chloro-6-fluoro-3-iodobenzaldehyde. 1HNMR (400 MHz, CDC13) delta 10.34 (s, 1H), 8.04 (m, 1H), 6.92 (dd, J = 9.4, 9.4 Hz, 1H).

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 101335-11-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
Iodide – Wikipedia,
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Synthetic Route of 460-37-7,Some common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, 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 stirred a solution of methyl-(2S)-2-(te/Y-butoxycarbonyl)-amino-2-[8-aza-bicyclo [3.2.1]-oct-3-yl]-exo-acetate (step 5 of intermediate 2, 1.0 g, 3.36 mmol) in acetonitrile (20 ml) at room temperature was added anhydrous K2CO3 (1.39g, 10.07 mmol) stirred for 10 minutes. To this reaction mixture was then added 3,3,3-trifluoropropyl iodide (0.827g, 0.43 ml, 3.69 mmol) and heated at 5O0C for 6 hours under stirring. The solvent was removed under reduced pressure and added ethyl acetate (50 ml). The organic layer was washed with water (2×20 ml), bromine (10 ml) and dried over anhydrous Na2SO4. The solvent was evaporated to yield the crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 1.3% methanol in dichloromethane as an eluent to yield the title compound (0.775g, 58%). MS: m/z 395(M+1) 1HNMR (CDCI3, 200 MHz): delta 1.17-1.60 (m, 15H), 1.82-2.40 (m, 5H), 2.5 -2.63 (m, 2H), 3.14- 3.28 (m, 2H) 3.73 (s, 3H) 4.10-4.30 (m, 1 H), 4.97-5.10 (m, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,1-Trifluoro-3-iodopropane, its application will become more common.

Reference:
Patent; LUPIN LIMITED; WO2009/37719; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 626-01-7, 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. 626-01-7 name is 3-Iodoaniline, 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: In a test tube equipped with a magnetic stirrer bar, thearyl halide 1 (1 mmol) was mixed with phenyl boricacid 2 (1.2 mmol), K2CO3(2 mmol), and the Pd-catalyst(0.1mol% Pd) in 2 ml of H2Oin air. The reaction mixturewas then stirred at 50 C for appropriate time. After completionof the reaction, the catalyst was removed by magnetand washed with ethanol and water (3 ¡Á 5 ml). The aqueouslayer was extracted with chloroform, then organic layerdried over anhydrous MgSO4.The solvent was evaporatedunder reduced pressure to give the corresponding biarylcompounds. All the products were previously reported [5,8-12] and were confirmed by the spectroscopic methodusing 1H and 13C NMR (see supporting information).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodoaniline, and friends who are interested can also refer to it.

Reference:
Article; Sarvi, Iraj; Gholizadeh, Mostafa; Izadyar, Mohammad; Catalysis Letters; vol. 147; 5; (2017); p. 1162 – 1171;,
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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 20555-91-3

A microwave vial was charged with palladium acetate (0.165 g, 0.733 mmol), l,2-dichloro-4-iodobenzene (2.00 g, 7.33 mmol), but-3-en-2-ol (0.793 g, 1 1.0 mmol), tetrabutylammonium chloride, hydrate (2.17 g, 7.33 mmol), and sodium bicarbonate (1.539 g, 18.32 mmol). DMF (5 mL) was added via syringe and the reaction mixture was degassed three times. The mixture was heated at 60 C for 16 h. The reaction mixture was allowed to cool to room temperature, and diluted with ether. The organic layer was washed with water, separated, dried with MgSC^, filtered and concentrated. The crude residue was purified by silica gel chromatography with an eluant of 10% ethyl acetate / hexanes to afford the desired product Intermediate 4A (1.4 g, 6.5 mmol, 88% yield). LC- MS (ESI) m/z 216.9 (M+H), RT = 2.01 min (Method B).

According to the analysis of related databases, 20555-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HU, Carol Hui; QIAO, Jennifer X.; WANG, Tammy C.; WO2013/151923; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

Under an argon atmosphere, a suspension of lithium chloride (113 mg, 2.66 mmol) in THF (5.3 mL)A THF solution (2 M, 1.33 mL, 2.66 mmol) of isopropyl magnesium chloride and 1-iodo-4- (trifluoromethyloxy) benzene (0.425 mL, 2.76 mmol) were added at room temperature,And the mixture was stirred for 3 hours.A solution of 2-fluoro-N-methyl-N-methyloxy-2- (1,2,4-triazol-1-yl) acetamide (200 mg, 1.06 mmol) in THF (3.5 mL) In addition,And the mixture was stirred at that temperature for 10 minutes.Saturated ammonium chloride aqueous solution was added to the reaction solution,And extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.The obtained crude product was purified by column chromatography (hexane: ethyl acetate = 10: 1 to 2: 1)2-fluoro-2- (1,2,4-triazol-1-yl) -1- [4- (trifluoromethyloxy) phenyl] ethanoneWhite solids(218 mg, yield: 71percent).

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; SAGAMI CHEMICAL RESEARCH INSTITUTE; HOKKO CHEMICAL INDUSTRY COMPANY LIMITED; HANDA, MASAMI; MIZUTA, SATOSHI; HIRAI, KENJI; OKAMURA, DAIGO; GUSHIKAWA, TORU; (111 pag.)JP2015/848; (2015); A;,
Iodide – Wikipedia,
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Electric Literature of 25309-64-2, 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. 25309-64-2, name is 1-Ethyl-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An appropriate phenylacetamide (0.12 mmol, 1 equiv), an appropriate iodo compound (0.48 mmol, 4 equiv), Pd(OAc)2 (2.7 mg, 10 mol%), and AgOAc (50 mg, 0.3 mmol, 2.5 equiv) in anhydrous toluene (3 mL) was heated at 110 C for 24 h under a nitrogen atmosphere. After the reaction period, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography furnished the corresponding arylated products 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) (see corresponding Tables/Schemes for specific examples and reaction conditions).

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

Reference:
Article; Bisht, Narendra; Babu, Srinivasarao Arulananda; Tetrahedron; vol. 72; 39; (2016); p. 5886 – 5897;,
Iodide – Wikipedia,
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