Month: January 2021

Adding a certain compound to certain chemical reactions, such as: 503821-94-1, name is 3-Bromo-2-iodobenzoic acid, 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 503821-94-1, Computed Properties of C7H4BrIO2

By the same procedure, using 3-bromo-2-iodo-benzoic acid as the starting material, 7-bromo-8-iodo-1,2,3,4-tetrahydroisoquinoline is prepared.

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; SmithKline Corporation; US3988339; (1976); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 175278-00-9, 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. 175278-00-9, name is 1-Iodo-2-(trifluoromethoxy)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 1-iodo-2-(trifluoromethoxy)benzene (23.2 g, 80.6 mmol), 1,1-dimethylethyl 1-piperazinecarboxylate (10 g, 53.7 mmol) and sodium tert-butoxide (7.2 g, 75.2 mmol) in toluene was degassed with bubbling nitrogen. (RS)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (334 mg, 0.54 mmol) and tris(dibenzylideneacetone)dipalladium (0) (492 mg, 0.54 mmol) were added, and the mixture was degassed and stirred at 80[deg.] C. for 48 h. The mixture was cooled, poured into water and extracted with ethyl acetate. The combined organic fractions were dried (MgSO4), filtered through a plug of silica gel, eluting with ethyl acetate, and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), hydrochloric acid (5M, 100 mL) was added and the mixture was stirred at room temperature overnight. The layers were separated and the organic layer was extracted with hydrochloric acid (5M). The combined aqueous extracts were washed with ether, basified with aqueous sodium hydroxide (4N) and extracted with ethyl acetate. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate-ether (1:1) and ethereal hydrogen chloride (1M, 40 mL) was added. The solid was collected and dried in vacuo to give the title compound as a light brown solid (9.5 g, 62%). H NMR (360 MHz, D2O) [delta]7.41-7.35 (2H, m), 7.26-7.19 (2H, m), 3.45-3.42 (4H, m), and 3.34-3.32 (4H, m). m/z (ES) 247 (M+1).

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-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US6518273; (2003); B1;,
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. 6940-76-7, name is 1-Chloro-3-iodopropane, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

Solution stirred between -20 an’d 1 0 C for 30 min and subsequently cooled to -78 C. A solution of tert-butyl 6-chloropyridin-2-ylcarbamate (108; 57.0g, 0.249mol) in TH F (300mL) was added over 1 5 min. The reaction mixture was aged for 1 hour and then Cul (47.6g, 0.249mol) was added in one portion. The reaction mixture was al lowed to warm to – 1 0 C for one hour. 1 – Chloro-3-iodopropane (76.5g, 0.374 mol) was added neat over a period of 1 min, the cooling bath was removed and reaction allowed to warm to ambient temp and subsequently refluxed overnight. Upon completion of the reaction, the reaction mixture was cooled and quenched via addition of saturated sodium bicarbonate. The aqueous layer was extracted with EtOAc, The combined organic layers were dried over a2S04, filtered through a short si lica gel pad, concentrated to afford crude product., Triturated with ether to afforded tert-butyl 7-chloro-3,4- dihydro- l ,8-naphthyridine- l (2H)-carboxylate (109; 43g, yield 67%). M S (ESI) calcd for C,3H17C1N202 (m/z) 268.74.

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; SIRTRIS PHARMACEUTICALS, INC.; NG, Pui, Yee; BLUM, Charles; MCPHERSON, Lauren; PERNI, Robert, B.; VU, Chi, B.; AHMED, Mohammed, Mahmood; DISCH, Jeremy, S.; WO2011/59839; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

355-43-1, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, 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. Formula: C6F13I

Cooled to -78 C. zirconocene dichloride(Cp 2 ZrCl 2, 70.2 mg, 0.24 mmol)Of ether (2.4 mL)To the solution was added n-propylmagnesium chloride (2.0 M in ether solution, 0.12 mL, 0.24 mmol)1,4-Dioxane (23 [mu] L, 0.27 mmol)And n-tridecafluorohexyl iodide (C 6 F 13 I, 78 muL, 0.36 mmol) were added,And the mixture was stirred at the same temperature for 1 hour.Then,Methylaluminoxane(10% toluene solution, 0.16 mL, 0.24 mmol) was added thereto, the temperature was raised to 0 C., and the mixture was stirred for 2 minutes. After adding styrene oxide (23 muL, 0.20 mmol) to this, the temperature was raised to room temperature and stirred for 1 hour.After completion of the reaction, 1 N hydrochloric acid was added to quench the reaction and then extracted 3 times with ether, and the organic layers were combinedDried over sodium sulfate, filtered and the solvent was distilled off under reduced pressure to give a crude product. The crude product obtainedThe product was purified by silica gel column chromatography (hexane / ethyl acetate = 20/1 (v / v)) To obtain 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecaFluoro-1-phenyl-2-hydroxyoctane (77.5 mg, yield: 88%).

The synthetic route of 355-43-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; TOSOH F-TECH INCORPORATED; MIKAMI, KOICHI; FUJIU, MOTOHIRO; (46 pag.)JP5894739; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-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. Product Details of 31599-61-8

Substrate 1 was arylated following the general arylation procedure A. Analysis of crude reaction mixture by XH NMR showed a > 20:1 ratio of mono- and diarylated products. After purification by column chromatography using toluene/EtOAc (30/1) as the eluent, Compound 2r was obtained as a white solid (47.0 mg, 87%). 1H NMR (600 MHz, CDC13) delta 8.44 (br s, 1H) , 7.83-7.80 (m, 2H) , 7.75-7.72 (m, 2H) , 6.97-6.96 (m, 2H) , 6.94-6.92 (m, 1H) , 5.31 (dd, sigma = 6.6 Hz, J2 = 10.2 Hz, 1H) , 3.58 (ABqd, J = 6.6 Hz, J2 = 14.4 Hz, 1H) , 3.48 (ABqd, Jj. = 10.2 Hz, J2 = 14.4 Hz, 1H) , 2.14 (s, 3H) , 2.11 (s, 3H) ; 13C NMR (150 MHz, CDC13) 5168.1, 166.7, 137.2, 135.7, 134.6, 132.7, 131.2, 130.13, 130.09, 126.1, 123.8, 56.6, 34.9, 19.5, 19.3; HRMS (ESI-TOF) Calcd for C26HIBF7N203 [M+H] + : 539.1200; found: 539.1195. Large scale reaction: Substrate Compound 1 (15 mmol, 6.51 g) , Pd(TFA)2 (1.5 mmol, 0.50 g) , and Ag2C03 (22.5 mmol, 6.12 g) were weighed in air and placed in a round-bottom flask (100 inL) with a magnetic stir bar. 4-Iodo-o-xylene (22.5 mmol, 5.22 g), 2-picoline (3.0 mmol, 0.28 g) , TFA (3.0 mmol, 0.34 g) , and DCE (50 mL) were added. The pressure vessel was sealed. The reaction mixture was first stirred at room temperature for 10 minutes and then heated to 100 C. Upon completion, the reaction mixture was purified by a silica gel-packed flash chromatography column, and Compound 2r was obtained in 79% yield (6.38 g) .

The synthetic route of 4-Iodo-1,2-dimethylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; WO2015/131100; (2015); 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 202982-68-1 as follows. Recommanded Product: 202982-68-1

Example 131. Preparation of (4-(2-chloro-5-fluorophenyl)piperazin-1-yl)(5-phenylisoxazol-3-yl)methanone (297) To a solution of (5-phenylisoxazol-3-yl)(piperazin-1-yl)methanone (0.25 g, 0.851 mmol) and 1-chloro-4-fluoro-2-iodobenzene (0.327 g, 1.28 mmol) in toluene (5 mL) was added cesium carbonate (0.832 g, 2.55 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.085 mmol) and BINAP (0.053 g, 0.085 mmol). The reaction mixture was purged with nitrogen for 3 min and stirred at 115 C. in a sealed tube for 15 h. The mixture was quenched with water (10 mL) and extracted with ethyl acetate (15 mL*3). The combined organic layers were washed with brine (5 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (ISCO, 10 g silica, 8-10% ethyl acetate in petroleum ether, gradient over 15 min) and then by prep-HPLC (YMC-Actus ODS-AQ 100*30 5 mum column; 45-85% acetonitrile in an a 0.05% hydrochloric acid solution in water, 12 min gradient) to give (4-(2-chloro-5-fluorophenyl)piperazin-1-yl)(5-phenylisoxazol-3-yl)methanone hydrochloride salt (0.172 g, 0.404 mmol, 47%) as a white solid. 1H NMR (400 MHz, Chloroform-d) delta 7.89-7.80 (m, 2H), 7.57-7.46 (m, 3H), 7.40-7.31 (m, 1H), 6.89 (s, 1H), 6.82-6.71 (m, 2H), 4.20-4.10 (m, 2H), 4.08-3.97 (m, 2H), 3.18-3.13 (m, 4H); LCMS (ESI) m/z: 386.0 [M+H]+.

According to the analysis of related databases, 202982-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); 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. 191348-14-8, name is 2-Iodo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Iodo-4-methoxyaniline

Under anhydrous and anaerobic conditions, 0.1 mmol of 2-iodo-4-methoxyaniline was added.0.12 mmol of 2-fluoro-4-methoxybenzaldehyde, 0.3 mmol of selenium powder,0.005 mmol of copper, 0.2 mmol of potassium hydroxide and 10 ml of DMSO solution,The reaction was refluxed at 120 C in a single-neck round bottom flask, and the reaction was monitored by TLC.Separation of pure methoxy-containing benzoselenazole compounds by column chromatographyThe reaction product was obtained by demethylation of boron tribromide (6 eq.).The product was a white solid with a yield of 29%.

According to the analysis of related databases, 191348-14-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan University; Zhou Haibing; Zhang Silong; Hu Zhiye; Li Yuanyuan; Ning Wentao; Dong Chune; (13 pag.)CN108863985; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

60577-34-6, name is 4-Iodo-N-methylaniline, 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: 60577-34-6

To a 250?mL round-bottomed flask equipped with a magnetic stir bar was added 4-iodo-N-methylaniline (2, 35.0?g, 150? mmol, 1 equiv) and 100?mL DCM. tBuONO (26.8?mL, 225?mmol, 1.5 equiv) was added dropwise into the flask under ice bath in 15?min. Then the reaction was allowed to proceed under stirring at r.t. for 4?h until the completion of reaction. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel with PE/EA (4:1) as the eluent and recrystallized in PE and DCM. The product 3 was obtained as a light yellow solid in 94% yield (37.0?g, 141?mmol). 1H NMR (500?MHz, CDCl3) delta 7.82-7.77 (m, 2H), 7.34-7.29 (m, 2H), 3.42 (s, 3H). 13C NMR (126?MHz, CDCl3) delta 142.01, 138.50, 120.53, 91.62, 30.97.

The synthetic route of 60577-34-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Zhongsu; Zeng, Hua; Zhang, Wenjing; Song, Chao; Yang, Fan; Liu, Yun; Zhu, Jin; Polymer; vol. 172; (2019); p. 152 – 159;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 1094759-93-9, name is 4-Chloro-5-fluoro-2-iodoaniline, 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. Application In Synthesis of 4-Chloro-5-fluoro-2-iodoaniline

To Intermediate 5A (47g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice H2O, the solids were filtered-off and washed with petroleum ether to afford 49 g Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+.

The synthetic route of 4-Chloro-5-fluoro-2-iodoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; WO2013/56060; (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. 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, A new synthetic method of this compound is introduced below., name: 2-(2-Iodophenyl)acetonitrile

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 ¡Á 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3ad; Yield: 40.5 mg (84%); fluorescent yellow solid; mp 193.7-194.6 C.

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; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com