Tag: M.W=200-300

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. 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 13421-00-6

Production example 15 5-Chloro-2-[[1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Following the procedure described in Production Example 7, the title compound was prepared from 5-chloro-2-iodobenzoic acid and 1-(2-pyridinyl)-1H-pyrazol-5-ylamine (88% yield). mp: 233-234C (recrystallized from ethanol). NMR (DMSO-d6) delta: 6.42 (1H, d, J=2.0Hz), 7.38 (1H, ddd, J=1.2Hz, 4.8Hz, 7.4Hz), 7.54 (1H, dd, J=2.6Hz, 8.8Hz), 7.63 (1H, d, J=8.8Hz), 7.71 (1H, d, J=2.0Hz), 7.88-7.92 (2H, m), 7.99-8.08 (1H, m), 8.47 (1H, dd, J=0.8Hz, 1.8Hz, 4.8Hz), 12.24 (1H, br s), hidden (1H).

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; Takeda Chemical Industries, Ltd.; EP1380296; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 138385-59-8, A common heterocyclic compound, 138385-59-8, name is 4-Iodo-2,6-dimethylaniline hydrochloride, molecular formula is C8H11ClIN, 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.

Z) -Methyl 3- (4-amino-3, 5-dimethylphenyl)-2- (benzyloxycarbonyl) acrylate; A 2 L round bottom flask, was charged with 4-iodo-2,6- dimethylbenzenamine hydrochloride salt (55 g, 194 mmol), methyl 2- (benzyloxycarbonyl) acrylate (59.2 g, 252 mmol), tetrabutylammonium chloride (59.2 g, 213 mmol), palladium acetate (4.34 g, 19.4 mmol), and tetrahydrofuran (1.2 L, degassed by a flow of nitrogen for 30 min). The mixture was stirred to form a suspension and degassed by a flow of nitrogen for 30 min. Triethylamine (110 mL, 789 mmol) was then added and the resulting mixture was heated at reflux for 3h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite and washed twice with tetrahydrofuran (2 x 100 mL). The solvents were removed and the residue was dissolved in methylene chloride which was extracted with water (3X), brine (2X), dried over sodium sulfate and concentrated. Column chromatography on silica gel using 1: 9 ethyl acetate/methylene chloride as eluent afforded a tan solid, which was recrystalized from methanol (210 mL) and water (100 mL). After filtration, the solid was washed with ice cold 1: 1 methanol/water mixture and then dried under high vacuum overnight at room temperature to afford the title compound (58.0 g, 65%) as a light tan solid. NMR shows a 2.7 : 1 ratio of Z and E isomers which were not separated.’H-NMR (DMSO-d6) 8 8.79 (s, 0.73H), 8.51 (s, 0.27 H), 7.40-7. 21 (m, 8H), 5.24 (s, 2H), 5.13 (s, 1.46 H), 5.00 (s, 0.54 H), 3.68 (s, 2.2 H), 3.61 (s, 0.8 H), 2.05 (s, 6H) ;’3C-NMR (DMSO-d6) 8166. 0,154. 7,146. 9, 137.2, 135.8, 130.9, 128.3, 127. 7, 127. 3,120. 3,120. 0,119. 4,65. 3,51. 7,17. 8.

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; BRISTOL-MYERS SQUIBB COMPANY; WO2005/56550; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 401-81-0, A common heterocyclic compound, 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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: 4-Iodoanisole (0.813 mmol, 200 mg), bis(pinacolato)diboron (1.219 mmol, 309 mg) were dissolved in 3 mL of dmf followed by copper ferrite nanoparticles (5mol% with respect to 4-iodoanisole) and potassiumtert-butoxide (1.219 mmol, 137 mg) were added to a 10 mLcapped vial and stirred at RT for time indicated. After stirring, the mixture was diluted with diethyl ether and filtered through celite bed. The filtrate was extracted with water (3 times) and the organic phase was dried over anhydrous MgSO4. The crude product was subjected to analyze by GC-MS. The conversion yield is accurately measured based on the consumption of 4-iodoanisole and the side product formed due to protodeiodination.

The synthetic route of 401-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohan, Balaji; Kang, Hyuntae; Park, Kang Hyun; Catalysis Communications; vol. 85; (2016); p. 61 – 65;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 60577-34-6,Some common heterocyclic compound, 60577-34-6, name is 4-Iodo-N-methylaniline, molecular formula is C7H8IN, 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.

Part D: The product obtained above was dissolved in dichloromethane (100 mL), to which DIEA (12 mL) and chloroacetyl chloride (12 mL) were slowly added at 0 C. The reaction was stirred from 0 C. to rt for 4 hours, washed with 1.0 N HCl (2*) and brine, and dried over magnesium sulfate. After solvent removal, the crude product was purified by chromatography using ethyl acetate/hexane as eluent (2:8 to 4:6 ethyl acetate:hexane) to give the desired 2-chloro-N-(4-iodo-phenyl)-N-methyl-acetamide as a brown solid. MS found: (M+1)+=310.23.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-N-methylaniline, its application will become more common.

Reference:
Patent; Smallheer, Joanne M.; Pinto, Donald J.; Wang, Shuaige; Qiao, Jennifer X.; Han, Wei; Hu, Zilun; US2004/6062; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13194-69-9, name is 2-Iodo-5-methylaniline, 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 13194-69-9, Recommanded Product: 2-Iodo-5-methylaniline

The corresponding imidazopyridine compound (0.2 mmol) and cuprous iodide (0.02 mmol) were sequentially added to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.2-iodo-5-methylaniline (0.5 mmol),1,10-azaphenanthrene (0.06 mmol), DBU (0.8 mmol),Carbon disulfide (0.4 mmol) and toluene (2.0 mL) were added by syringe under oxygen.The reaction tube was placed in a 120 C oil bath and stirred for 7 hours. The resulting solution was cooled to room temperature, and 2 mL of deionized water was added to the reaction mixture, and the mixture was uniformly mixed.Each time, 3 mL of ethyl acetate was used as an extractant to perform a liquid separation extraction operation.The crude product is extracted from the reaction liquid, and the extract is combined, and the solvent is removed by a rotary evaporator; the residue is purified by a silica gel column (silica gel size: 200 mesh to 300 mesh,The eluent is petroleum ether/ethyl acetate (6:1 v/v)).The target product was obtained in 64.5 mg, yield 80%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-5-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 3930-83-4, name is 2-Iodobenzamide, 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 3930-83-4, Recommanded Product: 2-Iodobenzamide

General procedure: To a solution of 2-iodobenzamide (3) or 2-bromonicotinamide (6) (2.0 mmol) in DMSO (3 mL), was added aldehyde (2.2 mmol), NaN3 (260 mg, 4.0 mmol), CuBr (29 mg, 0.2 mmol), and l-proline (46 mg, 0.4 mmol). The reaction mixture was stirred at 80 C under air. After disappearance of the reactant (monitored by TLC), water (30 mL) was added to the mixture, and then extracted with ethyl acetate (15 mL) for three times. The extraction was washed with saturated NaCl solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (10:1 to 3:1) as the eluent to give the desired products 5 or 7.

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:
Article; Li, Ting; Chen, Minglu; Yang, Lei; Xiong, Zhengxin; Wang, Yongwei; Li, Fei; Chen, Dongyin; Tetrahedron; vol. 72; 6; (2016); p. 868 – 874;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19094-56-5, name is 2-Chloro-5-iodobenzoic 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. name: 2-Chloro-5-iodobenzoic acid

Example 3; 4′-Chloro-3′-[[(cyclohexylmethyl)amino]carbonyl]-[l,l’-biphenyl]-2-carboxylic acid; EPO a) 2-Chloro-5-iodo-benzoic acid, 1,1-dimethylethyl ester; iV,iV-Dimethylformamide (1 drop) and oxalyl chloride (4.8 mL) were added to a stirred solution of 2-chloro-5-iodobenzoic acid (5 g) in dichloromethane (20 mL) at 0 C. The reaction was allowed to warm to room temperature, stirred under nitrogen for 2 hours, and then evaporated to dryness. The residue was dissolved in tetrahydrofuran (20 mL) and cooled to 0 0C. Potassium terf-butoxide (22 mL, 1 M solution in tetrahydrofuran) was added over 10 minutes. The reaction was allowed to warm to room temperature and stirred under nitrogen for 2 hours then poured into saturated aqueous sodium bicarbonate (50 mL). The layers were separated and the aqueous was extracted with diethyl ether (50 mL). The combined organics were dried, filtered and evaporated to afford the sub-title compound as an oil (5.7 g).1HNMR (400 MHz, d6-DMSO) delta 7.99 (IH, d), 7.87 (IH5 dd), 7.34 (IH, d), 1.54 (9H, s).

The synthetic route of 19094-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/80884; (2006); A1;,
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 33348-34-4 as follows. Recommanded Product: 33348-34-4

INTERMEDIATE 60 – PREPARATION of A/-(2-(5-Cyano-2-(triethylsilyl)-1 H-indol-3-yl)ethyl)-4- (3-fluorobenzyl)benzamide. 4-Amino-3-iodobenzonitrile (0.10 g; 0.41 mmol), 4-(3-fluorobenzyl)-/V-(4- (triethylsilyl)but-3-ynyl)benzamide (0.162 g; 0.41 mmol) bis(diphenylphosphino)ferrocene]palladium(ll) chloride (0.017 g; 0.020 mmol), lithium chloride (0.017 mg; 0.410 mmol) and sodium carbonate (0.087 g; 0.820 mmol) were suspended in DMF (5 ml_) and the mixture was stirred at 100C for 15 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60 % ethyl acetate in heptane) to afford 0.056 g (27%) of the title compound as a white solid. ESI/APCI(+): 512 (M+H), 534 (M+Na); ESI/APCI(-): 51 1 (M-H).

According to the analysis of related databases, 33348-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&D; REMYND; GRIFFIOEN, Gerard; VAN DOOREN, Tom; ROJAS DE LA PARRA, Veronica; ALLASIA, Sara; MARCHAND, Arnaud; KILONDA, Amuri; CHALTIN, Patrick; WO2012/80221; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 191348-14-8, name is 2-Iodo-4-methoxyaniline, 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 191348-14-8, name: 2-Iodo-4-methoxyaniline

General procedure: A quantitativeyield for the oxidation step (8?5)16 is presumed and hencethe molar amounts of each reagent are based on alcohol 8. Asealed tube charged with DMF (1-2 mL) was degassed withnitrogen for 30 min. Freshly prepared aldehyde 5 (0.15-0.26mmol) was added, followed by the appropriate o-iodoaniline6a-i (0.17-0.29 mmol), DABCO (0.45-0.79 mmol) andPd(OAc)2 (5 mol%). The tube was then sealed under ablanket of nitrogen and stirred at 85 C for 18-90 h. Thecooled solution was poured onto H2O (10 mL) and extractedwith Et2O (3 × 10 mL). The combined organic extracts weredried (MgSO4), filtered, and concentrated in vacuo.Purification by flash chromatography on silica gel (hexanes-EtOAc) gave the desired products 1a-i, the yields of whichwere calculated over two steps from alcohol 8.

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

Reference:
Article; Blair, Lachlan M.; Sperry, Jonathan; Synlett; vol. 24; 15; (2013); p. 1931 – 1936;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), molecular formula is C3H6I2, 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: 627-31-6

Compound 258g:[330] In a smal] vial dissolved Compound 8 (0.033 g, 0.112 mmol) in DMF (1.5 ml) with stirring at room temperature. 1,3-diiodopropane (0.065 ml, 0.561 mmol) was added fol]owed by the addition of potassium carbonate (0.023 g, 0.168 mmol). The reaction was covered in foil and stirred at room temperature overnight. The reaction was diluted with dichloromethane and washed with aqueous ammonium chloride and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica ptlc using 50% ethyl acetate in hexane to give Compound 258g (0.018 g, 0.039 mmol, 34.7 % yield). MS (mix), found 533.0 ([M]++K).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 627-31-6, its application will become more common.

Reference:
Patent; IMMUNOGEN, INC.; LI, Wei; FISHKIN, Nathan, Elliott; ZHAO, Robert, Yongxin; MILLER, Michael, Louis; CHARI, Ravi, V., J.; WO2010/91150; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com