Tag: M.W=300-400

Application of 689291-89-2, 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 689291-89-2 as follows.

To a stirred solution of 5-bromo-2-iodobenzaldehyde (4.2 g, 13.5 mmol, 1 .0 equiv) in THF (20 ml_) was added t-butyl amine (4.26 ml_, 40.6 mmol, 3.0 equiv) at room temperature, under nitrogen atmosphere. The reaction mixture was stirred for 40 h at room temperature and evaporated under vacuum to obtain a residue. The residue was dissolved in DCM (100 ml_) washed with H20 (50 ml_), dried over sodium sulphate and evaporated to obtain (£)-/V-(5-bromo-2-iodobenzylidene)-2-methylpropan-2-amine (3.0 g, crude) as a yellow oily compound. 1H NMR (400 MHz, CDCI3) delta ppm 1 .32 (s, 9H), 7.20 (dd, J=2.8, 8.4 Hz, 1 H), 7.68 (d, J=8.4 Hz, 1 H), 8.07 (d, J=2.4 Hz, 1 H), 8.31 (s, 1 H).

According to the analysis of related databases, 689291-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 450412-29-0, 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. 450412-29-0, name is 1-Bromo-3-fluoro-2-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

200 g (664 mmol) of 1-bromo-3-fluoro-2-iodobenzene,101 g (664 mmol) of 2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetraborate were dissolved in 1000 ml of THF and 600 ml of water and degassed.9.3 g (13.3 mmol) of bis (triphenylphosphine) palladium (II) dichloride and 1 g (20 mmol) of hydrazine hydroxide were added.The reaction mixture was stirred at 70 C for 48 hours under a protective atmosphere.Toluene was added to the cooled solution,Wash repeatedly with water, dry and concentrate.The product was purified by silica gel column chromatography with toluene / heptane (1: 2). Yield: 155 g (553 mmol),Theoretical yield 83%.

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-Bromo-3-fluoro-2-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; PARHAM, AMIR HOSSAIN; LUDEMANN, AURELIE; JOOSTEN, DOMINIK; GROSSMANN, TOBIAS; KROEBER, JONAS VALENTIN; (90 pag.)TW2017/31839; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 181765-86-6, 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. 181765-86-6 name is Methyl 5-bromo-2-iodobenzoate, 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.

A mixture of 1 ,4-benzenediboronic acid bis(pinacol) ester (4.40 g, 13.33 mmol), methyl 2-iodo-5-bromobenzoate (9.95 g, 29.18 mmol), and Aliquat 336 (1.60 mL) was degassed 3 times with N2 before 90.0 mL of dry toluene was added. Tetrakis(triphenylphosphine)palladium (1.50 g, 1.30 mmol) and IM aqueous sodium carbonate solution (5.73 g in 54.0 mL of water) which was already deaerated for 2 hours were added under N2. The mixture was stirred vigorously and heated at the refluxing temperature for 2 days and allowed to cool to room temperature. The solution was passed through a plug of Celite to remove palladium black and the filtrate was concentrated to provide a residue, which was purified by column chromatography (silica gel, chloroform) to afford 4,4″-dibromo-2,2″- methoxycarbonyl-[l,l’;4′,l “]terphenyl (17) as a white solid (6.00 g, 89% yield). 1H NMR (CDCl3): delta 3.72 (s, 6H), 7.32(d, 2H, J = 8.0 Hz), 7.33 (s, 4H), 7.69(d, 2H, J = 8.0 Hz), 8.01 (s, 2H) ppm.

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

Reference:
Patent; NORTHWESTERN UNIVERSITY; WO2009/17798; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 628-77-3, name is 1,5-Diiodopentane, 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 628-77-3, Product Details of 628-77-3

(S) – (4-hydroxy-5-methoxy-2-nitrophenyl) (2- (hydroxymethyl) -4-methylenepyrrolidin-1-yl) methanone (0.801 g, 2.60 mmol) in butanone (10 ml) was added Cs 2CO 3, (2.50 g, 7.67 mmol) , followed by addition of 1, 5-diiodopentane (415 mmol, 1.28 mmol) . The mixture was stirred for 26 h, concentrated and purified on SiO 2 column eluted with MeOH/CH 2Cl 2 (1: 15 to 1: 5) to afford the title compound (0.675 g, 77%yield, 95%pure) . MS ESI m/z calcd for C 33H 41N 4O 12 [M+H] + 685.26, found 685.60.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,5-Diiodopentane, and friends who are interested can also refer to it.

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); 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. 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Iodo-2-(2-iodoethoxy)ethane

A N,N-dimethylformamide (0.5 mL) solution of (ls,4s)-4-(4-(2-((2,6- difluorobenzyl)oxy)- 1,1,1 ,3 ,3 ,3 -hexafluoropropan-2-yl)phenyl)-4-((4- fluorophenyl)sulfonyl)cyclohexanamine (10 mg, 0.016 mmol), l-iodo-2-(2- iodoethoxy)ethane (15.63 mg, 0.048 mmol) and potassium carbonate (26 mg, 0.188 mmol) was stirred at room temperature for 3 days. LCMS analysis showed that the reaction was near completion. The mixture was diluted with ethanol (1 mL) and filtered. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge CI 8, 19 x 250 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 40-100% B over 25 minutes, then a 5- minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give Example 8 (4.5 mg, 36% yield). LC/MS (M+l): 696.3; LC retention time: 2.46 min (analytical HPLC Method B); 1H NMR (400 MHz, 1 : 1 mixture of CDC13-CD30D) delta ppm 7.60 (d, J=8.4 Hz, 2H), 7.43 – 7.34 (m, 3H), 7.24 (dd, J=8.9, 5.1 Hz, 2H), 7.02 – 6.90 (m, 4H), 4.73 (s, 2H), 3.79 (br. s., 3H), 2.81 (d, J=8.1 Hz, 2H), 2.51 (br. s., 3H), 2.28 – 2.06 (m, 5H), 1.46 – 1.20 (m, 4H).

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 34270-90-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUAN, Jingwu; DHAR, T. G. Murali; JIANG, Bin; KARMAKAR, Ananta; GUPTA, Arun Kumar; LU, Zhonghui; WEIGELT, Carolyn A.; WO2015/103507; (2015); 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. 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Iodo-3,5-bis(trifluoromethyl)benzene

Under a nitrogen atmosphere,Alpha-naphthol (7.2 g, 50 mmol),3,5-bis(trifluoromethyl)iodobenzene (20.4 g, 60 mmol),Barium carbonate (19.5 g, 60 mmol) was dissolved in 200 mL DMF.Additional palladium chloride (0.13 g, 0.75 mmol)As a catalyst,Heated at 115 ° C for 12 h,TLC monitors the progress of the reaction.The reaction is over,After falling to room temperature,Extracting the organic phase with ether,Dry over anhydrous MgSO4,filter,concentrate.Column chromatography gave the product as a dark brown oil.It was stirred and reacted with dihydropyran at room temperature for 10 h.A pale yellow solid k with a tetrahydropyran group is obtained.Under a nitrogen atmosphere,The intermediate product k (13.2 g, 30 mmol) was dissolved in 50 mLIn ether,The ice water bath is stable for 5 minutes.Add n-BuLi solution (14 mL, 33 mmol) dropwise.After 0.5 h of reaction, it gradually returned to room temperature.Continue to react for 4h,A large amount of white precipitate l was obtained.6.5 mL of diphenylphosphine chloride (PPh2Cl)Disperse evenly in 10 mL of ether,Under the ice water bath,Add dropwise to the original reaction system,Slowly rise to room temperature,The reaction was stirred overnight.TLC monitoring until the end of the reaction,Quenched with water,Extracting the organic phase with ether,The resulting organic phase was concentrated to 100 mL.Deaeration in the refrigeration cycle,Add 5 mL of concentrated hydrochloric acid under a nitrogen atmosphere.Reaction 5h,The reaction was followed by TLC.Neutralized by adding NaHCO3 aqueous solution,Quenched with water,Extracting the organic phase with ether,Dry over anhydrous MgSO4,filter,concentrate,Flash column chromatography gave 8.1 g of a white solid.The yield was 50percent.

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 328-73-4.

Reference:
Patent; Tianjin University; Li Yuesheng; Wang Xuling; Zhang Yanping; Pan Li; (25 pag.)CN109320558; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 61203-48-3, 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. 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 2.a. N-(6,7-Methylenedioxycinnolin-4-yl)-N-(N,N-diethylaminoethyl)- 2-iodo-4,5-dimethoxybenzamide: Prepared from N’-(6,7-Methylenedioxycinnolin-4- yl)-N,N-diethylethane-l,2-diamine (640 mg, 2.2 mmol); (87% yield); reaction time 16 h; IR (CHC13) 1656; 1H NMR (CDC13) delta 0.92 (t, 6H, J=7.0), 2.50 (q, 4H, J=7.0), 2.80 (t, 2H, J=6.8), 3.39 (s, 3H), 3.71 (s, 3H), 3.94 (m, 1H), 4.41 (m, 1H), 6.21 (d, 2H, J=1.4), 6.39 (s, 1H), 7.01 (s, 1H), 7.39 (s, 1H), 7.64 (s, 1H), 9.11 (s, 1H); 13C NMR (CDC13) delta 11.6, 46.9, 47.8, 51.1, 55.7, 56.1, 82.9, 96.9, 102.9, 105.5, 110.9, 122.1, 122.9, 133.0, 136.5, 144.9, 148.3, 150.1, 150.9, 151.7, 152.3, 169.8; HRMS calcd for C24H2705N4IH: 579.1105; found: 579.1105.

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-4,5-dimethoxybenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENZYME CORPORATION; TEICHER, Beverly, A.; SCHMID, Steven, M.; WO2012/15901; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

175278-30-5, name is 4-Bromo-2-ethyl-1-iodobenzene, 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. SDS of cas: 175278-30-5

20 g (64.3 mmol) of 1-iodo-2-ethyl-4-bromobenzene and 12 g (64.3 mmol) of 4-n-hexylphenylacetylene are initially introduced into 300 ml of triethylamine and 250 mg (1.3 mmol) Of copper (I) iodide and 900 mg (1.3 mmol) of bis (triphenylphosphine) palladium (II) chloride are added and the mixture is stirred at RT for 3 h and then refluxed for 1 h.Cool the batch, add water and heptane, and separate the phases. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO 2, heptane); the product is obtained as a colorless oil.

The synthetic route of 175278-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; JASPER, CHRISTIAN; MONTENEGRO, ELVIRA; PAULUTH, DETLEF; REIFFENRATH, VOLKER; MANABE, ATSUTAKA; (43 pag.)JP6218607; (2017); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 689260-53-5, These common heterocyclic compound, 689260-53-5, name is 2-Bromo-5-iodo-1,3-dimethylbenzene, 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.

Step 1: 1-(4-(4-Bromo-3,5-dimethylphenyl)-1H-pyrazol-1-yl)-2-methylpropan-2-ol A mixture of 2-bromo-5-iodo-1,3-dimethylbenzene (1.00 g), 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol (1.11 g), and 2 M aqueous Na2CO3 solution (4.0 mL) in N,N-dimethylformamide is purged with argon for 3 min. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (85 mg) is added and the mixture is stirred at 60 C. for 3 h. After cooling to room temperature the mixture is diluted with water and ethyl acetate. The organic phase is washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 11): tR=1.12 min; Mass spectrum (ESI+): m/z=323, 325 [M+H]+.

The synthetic route of 689260-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (2013); 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 34270-90-1 as follows. SDS of cas: 34270-90-1

General procedure: Step (1): Carry out substitution reaction using dimethyl 4-hydroxyphthalate as raw material;Specifically: put dimethyl 4-hydroxyphthalate and dihalo compound in anhydrous acetonitrile,Add an appropriate amount of cesium carbonate solid and stir at 80 C for 12 hours.The solid was removed by filtration, the filtrate was spin-dried, and purified by silica gel chromatography using petroleum ether / ethyl acetate or dichloromethane / methanol.

According to the analysis of related databases, 34270-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Peking University; Lei Xiaoguang; Tang Yuliang; Dong Mengqiu; Wang Jianhua; (26 pag.)CN110981715; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com