Tag: M.W=200-300

Some common heterocyclic compound, 123278-03-5, name is 3-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, 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. name: 3-Chloro-2-iodobenzoic acid

Step 1; A 100-mL flask was charged with 3-chloro-2-iodobenzoic (2.43 g, 8.64 mmol, 0.90 equiv) and thionyl chloride (15 mL). The solution was vigorously stirred, then 1 drop of DMF added and the mixture heated to reflux for 4 h. During this time the acid dissolved to give a pale yellow solution. The cooled mixture was evaporated and toluene (50 mL) added, then removed in vacuo. The evaporation/dissolution with toluene/evaporation procedure was repeated twice and the pale yellow 3-chloro-2-iodobenzoyl chloride was placed on the vacuum line.In a separate flask a toluene (30 mL) solution tert-butyl 4-oxopiperidine-1-carboxylate (2.45 g, 12.32 mmol, 1.25 equiv), 4-methoxybenzylamine (1.352 g, 9.6 mmol, 1.0 equiv) and MgSO4 (20 g) were heated to reflux overnight. The mixture was filtered through a bed of Celite, the cake was washed with toluene (30 mL) and the filtrate was evaporated. The amber residue was dissolved in CH2Cl2 (100 mL) and TEA (1.94 g, 2.7 mL, 19.2 mmol, 2.0 equiv) and DMAP (117 mg, 0.96 mmol, 0.1 equiv) were added. The 3-chloro-2-iodobenzoyl chloride prepared above was dissolved in CH2Cl2 (10 mL) and the resultant solution added to the enamine solution over a 10 min period, then stirred overnight. The reaction was quenched by addition of 1.0 M aq HCl (100 mL) and the mixture was transferred to a separatory funnel. The organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was purified by flash chromatography on silica gel (120 g) eluting with 19-71% EtOAc in hexanes tert-butyl 4-(3-chloro-2-iodo-N-(4-methoxybenzyl)benzamido)-5,6-dihydropyridine-1(2H)-carboxylate (3.19 g, 5.47 mmol, 63% yield), contaminated with 5% 3-chloro-2-iodo-N-(4-methoxy]benzyl)benzamide, was isolated as a pale yellow foam.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123278-03-5, its application will become more common.

Reference:
Patent; Claremon, David A.; Singh, Suresh B.; Tice, Colin M.; Ye, Yuanjie; Cacatian, Salvacion; He, Wei; Simpson, Robert; Xu, Zhenrong; Zhao, Wei; US2011/34455; (2011); A1;,
Iodide – Wikipedia,
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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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, A new synthetic method of this compound is introduced below., Formula: C6H3Cl2I

To a mixture of (1R, 3r, 5S) -tert-butyl 3-hydroxy-8-azabicyclo [3.2.1] octane-8-carboxylate (5.00 g, 22.00 mmol) in toluene (50 mL) was added 3, 5-dichloroiodobenzene (6.00 g, 22.00 mmol) , cesium carbonate (21.50 g, 66.00 mmol) , copper (I) iodide (0.63 g, 3.30 mmol) , 3, 4, 7, 8-tetramethyl-1, 10-phenantroline (1.60 g, 6.60 mmol) and molecular sieves (4A, 5.00 g) . The reaction mixture was degassed by passing a stream of argon through it and then heated at 80 in a sealed vial for 120 hours. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (150 mL) and filtered over diatomaceous earth. Concentration of the filtrate in vacuo gave a residue which was purified by flash chromatography (0 to 20ethyl acetate in hexanes) to afford the title compound as a yellowish oil (3.80 g, 46) :1H NMR (300 MHz, CDCl3) delta 6.93-6.90 (m, 1H) , 6.71-6.69 (m, 2H) , 4.59-4.53 (m, 1H) , 4.28-4.09 (m, 2H) , 2.24-1.85 (m, 8H) , 1.45 (s, 9H) MS (ES+) m/z 316.1, 318.1 (M -55) .

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

Reference:
Patent; GENENTECH, INC.; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BICHLER, Paul Robert; CHEN, Chien-An; CHOWDHURY, Sultan; DECKER, Shannon Marie; DEHNHARDT, Christoph Martin; FOCKEN, Thilo; GRIMWOOD, Michael Edward; HEMEON, Ivan William; JIA, Qi; LI, Jun; LIU, Zhiguo; ORTWINE, Daniel F.; SAFINA, Brian; SUTHERLIN, Daniel; SHENG, Tao; SUN, Shaoyi; WHITE, Andrew D.; WILSON, Michael Scott; ZENOVA, Alla Yurevna; ZHU, Jiuxiang; WO2015/78374; (2015); A1;,
Iodide – Wikipedia,
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Reference of 29289-13-2, 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. 29289-13-2, name is 2-Iodo-4-methylaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Preparation of 1-bromo-2-iodo-4-methylbenzene To a mixture of 2-iodo-4-methylaniline (50 g, 214.55 mmol) in HOAc (250 mL), H2SO4 (10 mL), and H2O (40 mL) was added a solution of NaNO2 (14.5 g) in H2O (80 mL) at 0 C. The solution was stirred for 1.5 h. This was defined as mixture A. In another round bottom flask, a mixture of NaBr (107 g), CuSO4 (32.2 g), Cu (38.9 g), H2SO4 (39 mL), and H2O (25 mL) was refluxed for 1.5 h. To this mixture was added mixture A, and the solution was then refluxed for 3 h. The solution was treated with water and extracted with EA (500 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and then concentrated in vacuo. Purification by column chromatography over silica gel eluted with PE afforded the product as colorless oil (43 g, yield 68%). 1H NMR (300 MHz, CDCl3): delta 7.69 (m, 1H), 7.47 (d, J=8.1 Hz, 1H), 7.00 (m, 1H), 2.26 (s, 3H) ppm.

The synthetic route of 2-Iodo-4-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; Akama, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131016; (2013); A1;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 13194-68-8, name is 4-Iodo-2-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 13194-68-8, Safety of 4-Iodo-2-methylaniline

A suspension of 4,5,6-trifluoro-isophthalic acid (1.03 g, 4.68 mmol) in freshly distilled THF (20 mL) at -78 C under nitrogen is treated with 2.0 equivalents of freshly prepared 1 M LiHMDS solution (HMDS, 2.07 mL, 9.83 mmol; n-butyllithium, 3.5 mL, 9.36 mmol) in THF. In a second flask is suspended 4-iodo-2-methylaniline (1.09 g, 4.68 mmol) in 20 mL of freshly distilled THF, cooled to -78 C. under nitrogen and treated with 2.0 equiv. of freshly prepared 1M LiHMDS solution (HMDS, 2.07 mL, 9.83 mmol; n-butyllithium, 3.5 mL, 9.36 mmol) in THF. After both solutions stirred for 30 minutes at -78 C., the benzoic acid solution was cannula transferred into the aniline solution and allowed to slowly warm to room temperature. After stirring for 4 hours, the reaction mixture was poured into 200 mL of a saturated HCl diethyl ether solution affording a white precipitate. The solid is filtered off and the remaining filtrate is collected and concentrated in vacuo affording 4,5-fluoro-6-(4-iodo-2-methyl-phenylamino)-isophthalic acid (1.55 g, 77%).

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, 4-Iodo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Biwersi, Cathlin; Tecle, Haile; Warmus, Joseph Scott; US2003/225076; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 19094-56-5, name is 2-Chloro-5-iodobenzoic 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. Safety of 2-Chloro-5-iodobenzoic acid

Analogous to the preparation of 4a, 2-chloro-5-iodobenzoic acid (2.81g, 10mmol) was treated with thionyl chloride (7 mL)

The synthetic route of 2-Chloro-5-iodobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhi, Ying; Gao, Li-Xin; Jin, Yi; Tang, Chun-Lan; Li, Jing-Ya; Li, Jia; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3670 – 3683;,
Iodide – Wikipedia,
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Some common heterocyclic compound, 83863-33-6, name is 5-Iodo-2-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. name: 5-Iodo-2-methylaniline

General procedure: The aromatic azides are prepared (Scheme 2) by addition of 6 NHCl solution to stirring dichloromethane solution of the appropriate amine at 0 C followed by drop wise saturated aqueous solution of NaNO2 and the contents stirred for 30 min. To the reaction mixture, added NaN3 stirred the contents for further 30 min.The contents were allowed to attain room temperature, the two phases were separated, and the aqueous phase extracted with DCM. The combined organic layers were washed with aqueous solution of NaHCO3, followed by then brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the aryl azides which were used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 83863-33-6, its application will become more common.

Reference:
Article; Majeed, Rabiya; Sangwan, Payare L.; Chinthakindi, Praveen K.; Khan, Imran; Dangroo, Nisar A.; Thota, Niranjan; Hamid, Abid; Sharma, Parduman R.; Saxena, Ajit K.; Koul, Surrinder; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 782 – 792;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, 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 5458-84-4, Quality Control of 1-Iodo-2-methoxy-4-nitrobenzene

A mixture of Cu l (6.80 g, 35.84 mmol ), CsF ( 14. 15 g, 93.18 mmol ) l -iodo-2-methoxy- 4-nitrobenzene ( 10 g, 35.84 mmol ) and sulfolane (20 ml ), was stirred rapidly at 45 C. To this mixture was added trimethyl(trifluoromethyl)silane ( 13.25 g, 93. 1 mmol ) dropwise over 4 hours using a syringe pump, and the resulting mixture was stirred at 45C for 1 8 hours. The mixture was diluted with ethyl acetate (500 mL ) and stirred with Celite for 5 min. The reaction mixture was filtered through a pad of Celite, diluted with ethyl acetate ( 500 mL ). The organic layer was washed with 10% NH4OH, 1.0 N HCl, brine, dried over Na2SC>4, filtered, and concentrated to give the crude product.The crude product was purified by chromatography (ethyl acetate/petroleum ether 0/1 to 1/4) to give intermediate 444 (8 g, 91% yield ) as a white solid.

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, 1-Iodo-2-methoxy-4-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 20691-72-9, name is 4-Iodo-2-nitroaniline, 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 20691-72-9. 20691-72-9

General procedure: Ra/Ni (0.4-0.5 g) was added in small portions to a stirred solution of 6.5 mmol of the required nitro compound (4-11) in 12 mL EtOH, 12 mL 1,2-dichloroethane and 2 mL (20 mmol) hydrazine hydrate at 30 C. After completion of the Ra/Ni addition, the mixture was heated in a water bath (50 C, 60 min) and filtered through celite. The filtrate was evaporated in vacuo and crude product used for further syntheses.

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 4-Iodo-2-nitroaniline.

Reference:
Article; Vasic, Vesna P.; Penjisevic, Jelena Z.; Novakovic, Irena T.; Sukalovic, Vladimir V.; Andric, Deana B.; Kostic-Rajacic, Sladana V.; Journal of the Serbian Chemical Society; vol. 79; 3; (2014); p. 277 – 282;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

123278-03-5, name is 3-Chloro-2-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. category: iodides-buliding-blocks

To a solution of 3-chloro-2-iodobenzoic acid (39.5 g, 140 mmol) in methylene chloride (500 ml) and N,N-dimethylformamide (1.083 ml, 13.98 mmol) was added thionyl chloride (20.41 ml, 280 mmol) dropwise. The mixture was stirred for 1 hour at room temperature and concentrated under reduced pressure to give 3-(3-chloro-2-iodophenyl)propanoyl chloride which was useddirectly in next step. To a stirred solution of N,N,O-trimethylhydroxylamine hydrochloride (20.47 g, 183 mmol) and 3-chloro-2-iodobenzoyl chloride (46 g, 153 mmol) in dry methylene chloride (500 ml) was added triethylamine (74.6 ml, 535 mmol) dropwise at 0C. The mixture was stirred for 4 hours at room temperature and then poured into water. The organic layer was separated, washed with water and brine, dried over Na2504, filtered and concentrated to afford the titlecompound.

The synthetic route of 123278-03-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; MICHAELIDES, Michael; HANSEN, Todd; DAI, Yujia; ZHU, Guidong; FREY, Robin; GONG, Jane; PENNING, Thomas; CURTIN, Michael; MCCLELLAN, William; CLARK, Richard; TORRENT, Maricel; MASTRACCHIO, Anthony; KESICKI, Edward A.; KLUGE, Arthur F.; PATANE, Michael A.; VAN DRIE, John H. Jr.; JI, Zhiqin; LAI, Chunqiu C.; WANG, Ce; (1190 pag.)WO2016/44770; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 34883-46-0, name is 1-Iodo-2-phenoxybenzene, 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 34883-46-0, Application In Synthesis of 1-Iodo-2-phenoxybenzene

In a 2L three-necked flask,Into 44.4g (150mmol, 1.0eq.) 2- iodo diphenyl ether,Dissolved with 1000 ml of chloroform,An additional 16.8 g (300 mmol, 2.0 eq.) of potassium hydroxide was added.95.85 g (600 mmol, 4.0 eq.) of liquid bromine was added dropwise at room temperature.After the completion of the dropwise addition, the reaction was stirred at room temperature for 12 hours.The reaction was quenched with a saturated Na 2 SO 3 solution, and a large amount of solid was precipitated, stirred, suction filtered, washed with water, washed with ethanol, and recrystallized from chloroform and ethanol.Finally, 50 g of Intermediate-1 was obtained in a yield of 73.3%.

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, 1-Iodo-2-phenoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Gao Guang Semiconductor Materials Co., Ltd.; Jin Zhenyu; Qian Chao; Guo Shuai; Dai Peipei; (35 pag.)CN108101922; (2018); A;,
Iodide – Wikipedia,
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