Tag: M.W=300-400

Application of 4897-68-1, A common heterocyclic compound, 4897-68-1, name is 1-Bromo-2-iodo-4-methoxybenzene, molecular formula is C7H6BrIO, 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: In an oven dried Schlenk tube under nitrogen atmosphere, were added allylic alcohol 6 (500.0mg, 1.76-3.38mmol), aryl halide 1 (2.11-4.06mmol), Pd(OAc)2 (11.8-22.7mg, 3mol%), triethylamine (356.2-684.1mg, 3.52-6.76mmol), followed by dry acetonitrile (4mL), at room temperature. The resulted reaction mixture was stirred for 24h at 80C. Progress of the reaction was monitored by TLC. The reaction mixture was quenched with the aqueous NH4Cl solution and extracted with ethyl acetate (3×20mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification of the residue on a silica gel column chromatography using petroleum ether/ethyl acetate as eluent furnished the ketone 7 (46-58%).

The synthetic route of 4897-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ramulu, B. Venkat; Mahendar; Krishna; Reddy, A. Gopi Krishna; Suchand; Satyanarayana; Tetrahedron; vol. 69; 38; (2013); p. 8305 – 8315;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25252-00-0, 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 25252-00-0 as follows.

Part C. 3′-(1-benzyl-6-cyano-1H-indol-3-ylmethyl)-4-carbamoyl-biphenyl-2-carboxylic acid benzyl ester:; 2-Bromo-5-iodobenzoic acid (6.54 g, 20.0 mmol) was dissolved in DMF (70 mL). Potassium bicarbonate (2.2 g, 22.0 mmol) was added, followed by benzyl bromide (2.8 mL, 22.0 mmol). The mixture was stirred at rt under N2 for 12 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic solution was washed with brine, dried over MgSO4, and concentrated and dried to give 9.05 g of the benzyl ester. The ester (2.3 g, 7.69 mmol), Zn(CN)2 (1.3 g, 11.5 mmol), and Pd[PPh3]4 were dissolved together in 25 mL of DMF. The mixture was de-gassed and heated at 90 C. for 4 h. Reaction mixture was concentrated and purified by chromatography (silica gel, 5% EtOAc in hexane) to give 1.8 g of the benzonitrile. MS: 316.0, 317.9 (M+1)+. The benzonitrile (1.4 g, 4.4 mmol) was dissolved in 15 mL of DMF. The reaction mixture was cooled at 0 C. Potassium carbonate (0.20 g, 1.45 mmol) was added, followed by dropwise addition of 30% hydrogen peroxide solution (1.2 mL). The cooling bath was removed and the mixture was stirred at rt for 12 h. The reaction was quenched with aqueous NaHSO3 and water. The formed precipitate was filtered and dried to give 1.1 g of the desired amide. MS: 334.2, 336.3 (M+1)+. A mixture of the resulting amide (0.2 g, 0.6 mmole), bis(pinacolato)diboron (0.228 g, 0.9 mmol) and anhydrous KOAc (0.18 g, 1.8 mmol) in 2 mL of 1,4-dioxane was purged with argon, then (1,1′)-bis(diphenylphosphino)ferrocene)palladium(II) chloride (20 mg, 0.024 mmol) was added. The resulting mixture was heated in a sealed tube in a microwave reactor at 100 C. for 2 h then left standing overnight at rt. The reaction was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the boronate (0.13 g, 57%). A mixture of this compound, the compound of Part B (0.1 g, 0.25 mmol), and K3PO4 (0.11 g, 0.5 mmol) in 5 mL dioxane was degassed and then treated with tetrakis(triphenylphosphine)palladium(20 mg, 0.017 mmol). The resulting mixture was heated in a 95-100 C. oil bath under N2 for 2 h, then stirred at rt overnight. The reaction mixture was diluted with brine and extracted 3× with EtOAc. The combined extracts were washed with brine then dried over anhydrous Na2CO3, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the product (0.12 g, 83%) as a light yellow foam. 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 2H) 4.90 (s, 2H) 5.23 (s, 2H) 6.91 (d, J=6.15 Hz, 2H) 7.05 (m, 3H) 7.20 (m, 6H) 7.29 (m, 5H) 7.42 (d, J=7.91 Hz, 1H) 7.51 (d, J=10.99 Hz, 2H) 7.98 (dd, J=8.13, 1.98 Hz, 1H) 8.19 (d, J=2.20 Hz, 1H). LC/MS m/z 576.16 (M+H)+.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, 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 755027-18-0, HPLC of Formula: C7H6BrIO

To a solution of l-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al., US 2004/0254159, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g, 133 mmol), Et3N (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 90C for 40 minutes, cooled to RT and poured into 2.4-L 1 M HCl. After stirring for 30 minutes, the solid was filtered, suspended in EtOH (230 mL) heated to reflux and allowed to cool to RT with stirring overnight. The solid was filtered and washed with 1 : 1 EtOH hexane (50 mL) to give the title compound. LRMS ESI+ (M+H)+ 257.0.

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; MERCK & CO., INC.; WO2008/57208; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 148870-57-9, 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. 148870-57-9 name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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 6 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one Based on EP 0 534 859 A solution of the (d) camphorsulphonate salt obtained in Example 5 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. Yield=64%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Les Laboratoires Servier; Vaysse-Ludot, Lucile; Le Flohic, Alexandre; Vaultier, Michel; Pucheault, Mathieu; Kaminski, Thomas; US8859763; (2014); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 774608-49-0, A common heterocyclic compound, 774608-49-0, name is 4-Bromo-1-chloro-2-iodobenzene, molecular formula is C6H3BrClI, 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.

j00340j To a solution of 4-bromo-1-chloro-2-iodobenzene (0.30 g, 0.95 mmol), cyclopropylboronic acid (97 mg, 1.1 mmol), [1,1 ?-bis(diphenylphosphino)ferrocenej dichloropalladium(II) (39 mg, 0.047 mmol) in dioxane (6 mL) and water (2 mL) under nitrogen at room temperature was added potassium phosphate (0.76 g, 3.6 mmol). The reaction mixture was stirred at 70 C for 3 hours, then diluted with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (2 xlO mL), dried over sodium sulfate, filtered and concentrated in vacuo to give compound B-34 (0.30 g, crude) as a yellow oil.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); 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. 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H6BrIO

To a solution of 4-bromo-1-iodo-2-methoxybenzene (1.634 g, 5.221 mmol) in dry acetonitrile (20 mL) Cul (49.7 mg, 0.261 mmol) and Pd(Ph3P)2Cl2 (183.2 mg, 0.261 mmol) were added under Argon atmosphere and the mixture was degassed and backfilled with Argon for three times. TEA (0.728 mL, 5.221 mmol) and (ethynyl)trimethylsilane(l .48 mL, 1.03 g, 10.442 mmol) were added with a syringe and the reaction mixture, that darkened within 10 min, was stirred at room temperature for 1 h. The solvent was removed under vacuum and the residue was taken up with EtOAc (100 mL), washed with brine (3 x 20 mL), water (20 mL), dried over sodium sulphate and evaporated to dryness. The crude was purified by chromatography on silica gel (petroleum ether/diethyl ether 9/1) to yield the title compound as an orange solid (1.426 g, 96.5%). 1H NMR (400 MHz, DMSO-cie) delta ppm 0.21 (s, 9 H) 3.83 (s, 3 H) 7.11 (dd, J=8.18, 1.83 Hz, 1 H) 7.26 (d, J=1.83 Hz, 1 H) 7.31 (d, J=8.06 Hz, 1 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; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria, Gabriella; BERTRAND, Jay, Aaron; GNOCCHI, Paola; MOTTO, Ilaria; NESI, Marcella; PANZERI, Achille; VIANELLO, Paola; WO2013/14039; (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. 148836-41-3, name is 1-Bromo-4-chloro-2-iodobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-4-chloro-2-iodobenzene

Step B: Preparation of l -Bromo-4-chloro-2-(3,3,3-triethoxyprop- l -ynyl)benzene; [08941 lambda mixture of l -bromo-4-chloro-2-iodoben/cne ( 1 0 g. 32 mmol) in 100 mL degassed ACN and TEA (29 g. 284 mmol), was treated with 3.3,3- triethoyprop- l -ync (6.0 g, 35 mmol), copper(l) iodide (0.60 g. 3.2 mmol), and dichltheta.Obis(triphenylphosphine)palladium(H) ( 1. 1 g, 1 .6 mmol). The mixture was stirred at room temperature for 2 hours at room temperature (the mixture turned dark green after 5 minutes). TLC showed that all starting material was converted, and a new spot was produced. The mixture was concentrated in vacuo. The residue was diluted with 100 ml. ether, washed with H2O (2 20 mL), 5% ammonia water (2 x 20 ml.), brine (20 ml.), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography pretreated with TEA and eluted with 0-15 % EtOAc/hexane to give 7.6 g of the product as a pale yellow oil. The oil solidified after it was stored in the refrigerator.

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; AMGEN INC.; WO2008/76427; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 112671-42-8, 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 112671-42-8 as follows.

Intermediate M3-a (3.7 g, 18.6 mmol) and 2-iodo-5-bromonitrobenzene (15.3 g, 46.7 mmol), sodium tert-butoxide(7.1 g, 74.4 mmol), 100 mL of toluene, nitrogen protection, Pd2 (dba) 3 (0.3 g),Tri-tert-butylphosphine (20ml, 10% in toluene), stirring, heating to 100 C reflux, reaction 12h, the reaction liquid was washed, the organic phase was concentrated, passed the silica gel column,The eluent is petroleum ether: ethyl acetate = 50:1, concentrated eluent,Intermediate M3-b (9.2 g, yield 82.7%) was obtained.

According to the analysis of related databases, 112671-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Fan Hongtao; Zhang Yaguang; Zhang Xianghui; Ren Xueyan; (36 pag.)CN108440543; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 63131-30-6, A common heterocyclic compound, 63131-30-6, name is Ethyl 3-(4-iodophenyl)-3-oxopropanoate, molecular formula is C11H11IO3, 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: To a solution of ethyl 3-oxo-3-(p-tolyl)propanoate (320 mg, 1.552 mmol) in dry DMF (3.1 mL) was added K2CO3 (236 mg, 1.707 mmol) followed by a solution of propargyl bromide in PhMe (9.2 M, 0.202 mL, 1.862 mmol). The reaction mixture was allowed to stir at ambient room temperature for 12 h. The reaction was transferred to a separatory funnel and diluted with deionized water (20 mL) and the aqueous layer was extracted with ethyl acetate (3 * 20 mL). The combined organic layers were sequentially washed with deionized water (20 mL) and brine (20 mL). The organic layer was dried over sodium sulfate then concentrated in vacuo. The crude material was then purified by flash column chromotography (3% EtOAc/Hexanes) to provide 10 (313 mg, 82%) as a yellow oil.

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:
Article; Golonka, Alexander N.; Schindler, Corinna S.; Tetrahedron; vol. 73; 29; (2017); p. 4109 – 4114;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 112671-42-8, name is 4-Bromo-1-iodo-2-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 112671-42-8, Recommanded Product: 4-Bromo-1-iodo-2-nitrobenzene

Under nitrogen conditions, 7H-diphenyl[c,g]carbazole (13.3 g, 49.92 mmol),4-bromo-1-iodo-2-nitrobenzene (32.74 g, 99.85 mmol),Potassium carbonate (13.8 g, 99.85 mmol), copper (6.35 g, 99.85 mmol),Stirring with ethylene glycol (350ml) at 100 CAfter stirring for about 1 hour, the reaction was completed, and after washing with deionized water,Recrystallization of acetone and methanol gave Intermediate 1-1 (15.9 g, 68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-iodo-2-nitrobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Jilin Aolaide Optoelectric Materials Co., Ltd.; He Jinxin; Jiang Zhiyuan; Jiang Xiaochen; Suo Hongguang; Wang Jinzheng; Jin Furong; (14 pag.)CN109422756; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com