Iodides-buliding-blocks

Electric Literature of 52548-63-7,Some common heterocyclic compound, 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, molecular formula is C7H4FIO2, 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.

To a solution of 3-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrrolo[2,3-c]pyridine (9.0 g, 34.84 mmol) in 200 mL of anhydrous DMF was added 5-fluoro-2-iodobenzoic acid (9.3 g, 34.84 mmol), Cu (442 mg, 6.97 mmol) and K2CO3 (14.4 g, 104.52 mmol). The resulting mixture was degassed and purged with N2 3 times, then stirred at 130 oC for 24 h under N2. The reaction mixture was then filtered through celite. The filtered cake was washed with EtOAc (150 mL) and the filtrate was concentrated under reduced pressure to remove most of the EtOAc and DMF. The resulting residue was poured into water (300 mL). The aqueous layer was adjusted by 6 N HCl to pH = 6-7, extracted with EtOAc (3 × 300 mL), and some white precipitate was formed. The suspension was then filtered. The filtered cake was collected and dried under reduced pressure to give a first batch of 2-(3- (1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)-5-fluorobenzoic acid (7.5 g) as white solid. The organic layers was washed with brine (3 × 300 mL), then dried over anhydrous Na2SO4, filtered and filtrate was concentrated under reduced pressure to give a second batch of 2-(3-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrrolo[2,3-c]pyridin-1- yl)-5-fluorobenzoic acid (4.5 g) as brown solid. Yield: 12.0 g (87%); LCMS method E: Rt = 0.649 min; (M+H)+ = 397.0.1H NMR (DMSO-d6): delta ppm 8.45 (s, 1H), 8.20-8.22 (d, J = 5.6, 1H), 7.60-7.80 (m, 4H), 7.53 (s, 1H), 3.95 (4, 1H), 2.90-3.00 (m, 1H), 2.03-2.10 (m, 2H), 1.65-1.85 (m, 6H).19F NMR (DMSO-d6): delta ppm -112.83.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Fluoro-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 156150-67-3, name is 2-Chloro-1-fluoro-4-iodobenzene, 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 156150-67-3, Formula: C6H3ClFI

Intermediate 5: Ethyl 1-(3-chloro-4-fluorophenyl)-5-methyl-1 H-1 ,2,3-triazole-4- carboxylate; To a mixture of 2-chloro-1-fluoro-4-iodobenzene (0.5 g, 1.950 mmol) and ethyl 2- butynoate (0.227 ml, 1.950 mmol) in water/DMSO (0.22ml/2ml) at room temperature was added L-proline (0.045 g, 0.390 mmol), sodium carbonate (0.041 g, 0.390 mmol), sodium azide (0.152 g, 2.340 mmol), sodium l-ascorbate (0.039 g, 0.195 mmol) and copper(ll) sulfate pentahydrate (0.024 g, 0.097 mmol) (in this order) and the mixture was heated at 65 0C overnight. On cooling to room temperature, the mixture was quenched with aqueous ammonia (1 ml) and EtOAc (20ml) and water (20 ml) were added. The two phases were separated, and the aqueous phase was extracted with EtOAc (3 x 30 ml). All organic phases were combined and washed with water/brine (50ml) repeatedly. The organic phase was dried over sodium sulfate, filtered and the solvent was evaporated to afford a crude product that was purified by MDAP to afford the title compound (6.5%); MH+=284.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/115486; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 13194-68-8, These common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, 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.

(b) Preparation of 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic Acid To a stirred solution comprised of 1.88 g (0.00791 mol) of 2-amino-5-iodotoluene in 10 mL of tetrahydrofuran at -78 C. was added 6 MnL (0.012 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 10 minutes, after which time a solution of 1.00 g (0.00392 mol) of 5-bromo-2,3,4-trifluorobenzoic acid in 15 mL of tetrahydrofuran was added. The cold bath was subsequently removed, and the reaction mixture stirred for 18 hours. The mixture was concentrated, and the concentrate was treated with 100 mL of dilute (10%) aqueous hydrochloric acid. The resulting suspension was extracted with ether (2*150 mL), and the combined organic extractions were dried (MgSO4) and concentrated in vacuo to give an orange solid. The solid was triturated with boiling dichloromethane, cooled to ambient temperature, and collected by filtration. The solid was rinsed with dichloromethane, and dried in the vacuum-oven (80 C.) to afford 1.39 g (76%) of a yellow-green powder; mp 259.5-262 C.; 1H NMR (400 MHz, DMSO): delta 9.03 (s, 1H), 7.99 (dd, 1H, J=7.5, 1.9 Hz), 7.57 (dd, 1H, J=1.5 Hz), 7.42 (dd, 1H, J=8.4, 1.9 Hz), 6.70 (dd, 1H, J=8.4, 6.0 Hz), 2.24 (s, 3H); 19F NMR (376 MHz, DMSO): delta -123.40 to -123.47 (m); -139.00 to -139.14 (m); IR (KBr) 1667 (C=O stretch)cm-1; MS (CI) M+1=469. Analysis calculated for C14H9BrF2INO2: C, 35.93; H, 1.94; N, 2.99; Br, 17.07; F, 8.12; I, 27.11. Found: C, 36.15; H, 1.91; N, 2.70; Br, 16.40; F, 8.46; I, 26.05.

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US6696440; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 364-12-5, 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. 364-12-5, name is 5-Bromo-2-iodobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows.

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

Reference:
Article; Nino, Patricia; Caba, Marta; Aguilar, Nuria; Terricabras, Emma; Albericio, Fernando; Fernandez, Joan-Carles; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 7; (2016); p. 854 – 881;,
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 444-29-1 as follows. COA of Formula: C7H4F3I

General procedure: A solution of Ar3In or (RC?C)3In (0.37mmol, ca. 0.18M in dry THF) was added to a mixture of MCM-41-N,N-Pd(0) (25mg, 1molpercent) and aryl iodide (1mmol) in dry THF (2mL) under Ar. The resulting mixture was refluxed under Ar until the starting material had been consumed (TLC). After being cooled to room temperature, the mixture was diluted with Et2O (30mL) and filtered. The palladium catalyst was washed with DMF (2×5mL), Et2O (2×5mL) and reused in the next run. The filtrate was washed with sat. aq NaHCO3 (5mL), water (3×10mL) and dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel to give the desired cross-coupling product.

According to the analysis of related databases, 444-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lei, Zhiwei; Liu, Haiyi; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 852; (2017); p. 54 – 63;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 29289-13-2, 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. 29289-13-2 name is 2-Iodo-4-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.

General procedure: A mixture of 2-halobenzenamine (1.0 mmol), isothiocyanate (1.2 mmol), Et3N (2.0 mmol) and MCM-41-2N-CuSO4 (0.0025 mmol) in DMSO (2 mL) was stirred under an air atmosphere at 80 C for 5-24 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature. The solution was diluted with ethyl acetate (30 mL ) and filtered. The catalyst was washed with ethyl acetate (2 × 5 mL) and Et2O (2 × 5 mL) and reused in the next run. The organic layer was washed with water (2 × 10 mL) and dried over anhydrous Na2SO4. After evaporating under vacuum, the residue was purified by flash chromatography on silica gel (petroleum/ethyl acetate = 10:1 to 4:1) to provide the corresponding pure product 3.

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

Reference:
Article; Xiao, Ruian; Hao, Wenyan; Ai, Jinting; Cai, Ming-Zhong; Journal of Organometallic Chemistry; vol. 705; (2012); p. 44 – 50;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 181765-86-6

Add compound 7 (9.99 g, 29.4 mmol) to a 250 ml three-necked flaskAnd p-methoxyphenylboronic acid (5.36g, 35.28mmol),Then add 50ml of tetrahydrofuran and 50ml of water and stir,Add bistriphenylphosphonium palladium dichloride (1.03g, 1.47mmol) under a nitrogen atmosphere.When the temperature reached 60 C, sodium carbonate (6.23g, 58.8mmol) was added, and the reaction was refluxed for 12h.Cooled to room temperature, diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate,After filtration, the solution was concentrated under reduced pressure and separated by column chromatography to obtain 7.53 g.Compound 8 was a white solid with a yield of 80%.

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian University of Technology; Wang Shisheng; Li Guangzhe; Liu Liqiang; Zhao Weijie; Guo Xiuhan; Li Yueqing; Wang Xu; Dong Huijuan; (21 pag.)CN110041200; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 58755-70-7,Some common heterocyclic compound, 58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, molecular formula is C7H6INO3, 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.

Example 2 Compound 6 Compound 6 was prepared from compound 5 (3.35 g, 12 mmol), trimethylsilylacetylene (3.3 mL, 24 mmol), PdCI2(PPh3)2 (0.42 g, 5.0 mol %), and CuI (0.114 g, 5.0 mol %) in TEA (70 mL). The reaction mixture was diluted with EtOAC and filtered through a silica gel bed, the organic layer was washed with water, and dried over Na2SO4. The dried organic layer was concentrated and purfied by chromatographic separation using (Hex:AcOEt = 100:10(v/v)) gave 1.66 g (55%) of compound 6.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-4-methoxy-2-nitrobenzene, its application will become more common.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2006/57946; (2006); A2;,
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. 3930-83-4, name is 2-Iodobenzamide, A new synthetic method of this compound is introduced below., COA of Formula: C7H6INO

General procedure: A two-neck round bottom flask was charged with amagnetic stirrer, evacuated and backfilled with argon. 2-iodobenzamide ( 0.5mmol, 124 mg), aniline or alpha-substituted benzylamine (1.0 mmol), K2CO3(1.0 mmol, 138 mg) and CuBr2 (0.05mmol, 11 mg) in DMSO (5 mL) under argon atmosphere. The mixture was allowed tostir under argon atmosphere at 110 C for 4 h.The mixture was concentrated with the aid of a rotary evaporator, and theresidue was purified by column chromatography on silica gel using petroleumether/ethyl acetate (2:1) as eluent to provide the product 2-9.

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; Wang, Li-Xia; Hu, Ben-Quan; Xiang, Jun-Feng; Cui, Jie; Hao, Xiang; Liang, Tong-Ling; Tang, Ya-Lin; Tetrahedron; vol. 70; 45; (2014); p. 8588 – 8591;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 1829-28-3,Some common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.

Weighing 5.52 g (20 mmol) of o-iodobenzoic acid ethyl ester obtained by esterification of o-iodobenzoic acid with anhydrous ethanol in a microwave reaction tube, 1.08 g (10 mmol) of o-phenylenediamine.Add copper iodide (190 mg, 1 mmol) in turn,Potassium phosphate (6.36g, 30mmol),Appropriate amount of ethylene glycol and magnetron at 180 C,Microwave reaction under nitrogen protection,The reaction was stopped after 1 h, and the reaction was terminated by TLC. Extraction with ethyl acetate (3 x 100 mL),Wash with water and an appropriate amount of saturated brine, combine the organic layers, add anhydrous Na2SO4 to remove water,After filtration, the residue was concentrated and the residue was purified by column chromatography to yield 1.The yield of the obtained Compound 1 was 65%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-iodobenzoate, its application will become more common.

Reference:
Patent; Xinxiang Medical University; Yan Fulin; Cao Ke; Yan Jianwei; Ma Lijuan; Lv Haixia; Wang Yawen; Yin Tiantian; (25 pag.)CN108586364; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com