Month: June 2021

Electric Literature of 13194-68-8, 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. 13194-68-8 name is 4-Iodo-2-methylaniline, 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.

EXAMPLE 1 4-Fluoro-2-(4-iodo-2-methylphenylamino)benzoic acid To a stirring solution comprised of 3.16 g (0.0133 mol) of 2-amino-5-iodotoluene in 5 mL of tetrahydrofuran at -78 C. was added 10 mL (0.020 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethenylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 15 minutes, after which time a solution of 1.00 g (0.00632 mol) of 2,4-difluorobenzoic acid in 10 mL of tetrahydrofuran was added. The reaction temperature was allowed to increase slowly to room temperature, at which temperature it was stirred for 2 days. The reaction mixture was concentrated. Aqueous HCl (10%) was added to the concentrate, and the solution was extracted with dichloromethane. The organic phase was dried (MgSO4) and then boiled over a steambath to low volume and cooled to room temperature. The off-white fibers were collected by vacuum filtration, rinsed with hexanes, and vacuum-oven dried. (76 C.; ca. 10 mm of Hg) to afford 1.10 g (47%) of the desired material; mp 224-229.5 C.; 1H NMR (400 MHz; DMSO): delta 9.72 (s, 1H), 7.97 (dd, 1H, J=7.0, 8.7 Hz), 7.70 (d, 1H, J=1.5 Hz), 7.57 (dd, 1H, J=8.4, 1.9 Hz), 7.17 (d, 1H, J=8.2 Hz), 6.61-6.53 (m, 2H), 2.18 (s, 3H); 13C NMR (100 MHz; DMSO): delta 169.87, 167.60, 165.12, 150.17, 150.05, 139.83, 138.49, 136.07, 135.31, 135.20, 135.07, 125.60, 109.32, 105.09, 104.87, 99.72, 99.46, 89.43, 17.52; 19F NMR (376 MHz; DMSO): delta-104.00 to -104.07 (m); IR (KBr) 1670 (C=0 stretch) cm-1; MS (CI) M+1=372. Analysis calculated for C14H11FINO2: C, 45.31; H, 2.99; N, 3.77. Found: C, 45.21; H, 2.77; N, 3.64.

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

Reference:
Patent; Gowan, Richard Carleton; Sebolt-Leopold, Judith; US2004/171632; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5471-81-8, name is Methyl 4-iodo-3-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 5471-81-8, Product Details of 5471-81-8

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10 mol%), methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),(4R)-4-((3S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadehydro-1H-cyclopenta[a]phenanthrene- 17-yl)pentanoic acid (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone (1.0 mL).The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C and stirred 24hour. After the reaction mixture was cooled to EtOAc EtOAc EtOAc m. Purified by column chromatography, the eluent was toluene: diethyl ether = 2:1 (v/v),(2R)-7-Methyl-2-(((4R)-4-((3S,8R,9S,10S,13R,14S,17R)-10,13-dimethylhexadecahydro-3) -Hydroxy-1H-cyclopentadieno[a]phenanthrene-17-yl)pentanoyl)oxy)methyl)-2,3-dihydrobenzofuran-5-carboxylic acid methyl ester 99 mg (colorless oily liquid) ,Yield 85%).

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; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 3718-88-5, These common heterocyclic compound, 3718-88-5, name is 3-Iodobenzylamine hydrochloride, 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.

The intermediate compound prepared in Step 1 (204 mg, 0.32 mmol) and3-iodo-benzylamine hydrochloride (113 mg, 0.41mmol) toIn absolute ethanol (5 mL) under nitrogen gas streamTriethylamine (0.13 mL, 0.96 mmol) was dissolved by stirring at room temperature for 24 hours.Remove the completed residue obtained by concentrated under reduced pressure, the reaction solution after confirming the reaction by column chromatography to intermediate compound (2R, 3S, 4S, 5R) -2- (benzoyloxy-methyl) -5- (2-chloro-6 (3-iodo-benzyl-amino) -9H- purin-9-yl) tetrahydrofuran-3,4-di yl benzoate (230 mg, to obtain a 86.14%).

Statistics shows that 3-Iodobenzylamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 3718-88-5.

Reference:
Patent; Korea University Industry-Academic Cooperation Agency; Kim, Won Gi; Choe, Yong Suk; (44 pag.)KR2015/10195; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 5471-81-8, 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 5471-81-8 as follows.

A solution of methyl 4-iodo-3-methylbenzoate (21 .7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -155C, /-PrMgCI (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2 h at -155C and then warmed to 255C and allowed to react for an additional hour. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08g .Yield: 80%). 1 H NMR (400 MHz, CDCI3) delta 10.35 (1 H, s), 8.00 (1 H, d, J=8Hz), 7.99 (1 H, s), 7.86 (1 H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) LC-MS: tR = 2.85 [M+H]+ = not ion (method 3).

According to the analysis of related databases, 5471-81-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; DRACONIS PHARMA, S.L.; LABORATORIOS DEL DR. ESTEVE, S.A.; AGUILAR, Nuria; FERNANDEZ, Joan, Carles; TERRICABRAS, Emma; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/149997; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. name: 3-Iodobenzonitrile

General procedure: A mixture of aryl iodide (1.00 equiv), organostannane(1.00 equiv) and cesium fluoride (3.00 equiv) in DMF was cooledto 0C and degassed for 10 min with argon. Then Pd(PPh3)4(0.10 equiv) and CuI (1.20 equiv) were added to the mixture and the reaction mixture was stirred for 0.5 h at 60C under argon.After the reaction was complete, the reaction mixture was diluted with CH2Cl2 and water, shaken vigorously and filtered through celite with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, and concentrated. The product was purified by column chromatography on silica gelusing ethyl acetate-hexanes.

The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hoshi, Ayako; Sakamoto, Takeshi; Takayama, Jun; Xuan, Meiyan; Okazaki, Mari; Hartman, Tracy L.; Buckheit, Robert W.; Pannecouque, Christophe; Cushman, Mark; Bioorganic and Medicinal Chemistry; vol. 24; 13; (2016); p. 3006 – 3022;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 645-00-1, 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. 645-00-1, name is 1-Iodo-3-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows.

The chemoselective hydrogenation of nitroarenes was performed in batch reactors. The reactant, internal standard (dodecane), solvent (toluene or THF), and powder catalyst, as well as a magnetic bar, were added into the batch reactor. After the reactor was sealed, air was purged by flushing two times with 10 bar of hydrogen. Then the autoclave was pressurized with H2 to the corresponding pressure. The stirring speed was kept at 800 rpm and the size of the catalyst powder was below 0.02 mm to avoid either external or internal diffusion limitation. Finally, the batch reactor was heated to the target temperature. For the kinetic studies, 50 muL of the mixture was taken out for GC analysis at different reaction times. For the scope studies, 100 muL of the mixture wastaken out for GC analysis. The products were also analyzed byGC-MS.

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

Reference:
Article; Liu, Lichen; Concepcion, Patricia; Corma, Avelino; Journal of Catalysis; vol. 340; (2016); p. 1 – 9;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 3058-39-7, 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 3058-39-7 as follows.

General procedure: A 10 mL round-bottom flask was charged with iodobenzene (4a, 1 mmol, 1 eq.), butyl acrylate (5, 1.5 mmol, 1.5 eq.), tributylamine (3 mmol, 3 eq.), H2O (2 mL), and Pd catalyst (0.01 mmol). The flask was stirred at 90 C in air. The reaction was monitored by thin layer chromatography (TLC) and gas chromatography (GC). After the reaction was complete, the reaction mixture was cooled to room temperature and then simply filtered to recover the catalyst. It was then washed with 10mL of H2O and ethyl acetate (EtOAc). The organic phase was separated from the aqueous phase, which was extracted three times with 30 mL EtOAc. The organic phases were collected together, dried over MgSO4, and filtered. The solvent was then evaporated under reduced pressure. Pure product was obtained via silica gel column chromatography with an eluent of EtOAc and hexane. The resulting product was analyzed by 1H NMR spectroscopy.

According to the analysis of related databases, 3058-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lee, Yongwoo; Hong, Myeng Chan; Ahn, Hyunseok; Yu, Jeongmok; Rhee, Hakjune; Journal of Organometallic Chemistry; vol. 769; (2014); p. 80 – 93;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 624-76-0, These common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, 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.

Compound 4a (617mg, 4.6mmol) was reacted with 2-Iodoethanol (0.54mls, 6.9mmol) and diisopropylethylamine (1.2mls, 6.9mmol) in ACN (20mls) at 30oC for 48 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane and EtOAc to provide the compound (483mg, 2.7mmol, 59% yield) as a light brown oil. HRMS (ESI, positive) m/z calcd. for C11H18N1O1 [M+H]+: 180.13829, found: 180.13829. 1H NMR (400 MHz, CDCl3) delta 7.28 – 7.19 (t, J = 8.0 Hz, 2H), 6.92 – 6.85 (d, J = 8.2 Hz, 2H), 6.83 – 6.75 (t, J = 7.3 Hz, 1H), 4.03 – 3.88 (hept, J = 6.6 Hz, 1H), 3.70 – 3.62 (t, J = 6.2 Hz, 2H), 3.34 – 3.24 (m, 2H), 1.19 – 1.12 (d, J = 6.6 Hz, 6H).

Statistics shows that 2-Iodoethanol is playing an increasingly important role. we look forward to future research findings about 624-76-0.

Reference:
Article; Bell-Horwath, Tiffany R.; Vadukoot, Anish K.; Thowfeik, Fathima Shazna; Li, Guorui; Wunderlich, Mark; Mulloy, James C.; Merino, Edward J.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2951 – 2954;,
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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,2-Difluoro-4-iodobenzene

A a solution of /Patent; CENTAURUS THERAPEUTICS; ROMERO, Donna, L.; BLITZER, Jeremy; (242 pag.)WO2019/140188; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 97456-81-0,Some common heterocyclic compound, 97456-81-0, name is 1-Bromo-3-iodo-2-methylbenzene, molecular formula is C7H6BrI, 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 microwave vial under Ar was charged with ieri-butyl 1-piperazinecarboxylate (154 mg, 0.825 mmol), NaO-i-Bu (95.2 mg, 0.990 mmol), (rac)-BINAP (39.3 mg, 0.0619 mmol, 7.5% mol), Pd2(dba)3 (19.2 mg, 0.0206 mmol, 2.5% mol in Pd), and degassed toluene (2.1 mL). 2-Bromo-6-iodotoluene (121 muL, 0.825 mmol) was then added, and the mixture was heated in sealed vial at 80 C for 19 h, cooled to rt, diluted with CH2CI2, filtered over Celite, and concentrated. The mixture was purified by chromatography on S1O2 (10% EtOAc hexanes) to afford the product as a yellow oil (95 mg, 0.27 mmol, 32%): NMR (500 MHz, CDCI3) delta 7.30 (d, J = 8.0 Hz, 1 H), 7.02 (t, J = 8.0 Hz, 1 H), 6.95 (d, J = 7.5 Hz, 1 H), 3.57 (m, 4 H), 2.83 (t, J = 4.5 Hz, 4 H), 2.40 (s, 3 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-Bromo-3-iodo-2-methylbenzene, its application will become more common.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; SKODA, Erin, M.; WANG, Zhou; WO2015/42297; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com