Month: November 2020

The chemical industry reduces the impact on the environment during synthesis 116632-39-4, name is 5-Bromo-2-iodotoluene, I believe this compound will play a more active role in future production and life. 116632-39-4

3OA: 4-bromo-2-methyH-vinylbenzene; [00347] KF (870 mg, 15 mmol), K-Bu4NCl (2.77 g, 10 mmol), Pd(dba)2 (145 mg, 0.25 mmol), molecular sieves (4 Ang, 200 mg, activated balls), 5-bromo-2-iodo- 1-methylbenzene (1.49 g, 5 mmol), trimethyl(vinyl)silane (2.7 mL, 20 mmol), and toluene (10 mL) were added to a pressure vessel and sparged with Ar. The vial was sealed and microwaved at 1700C for 30 min. The mixture was cooled to ambient temperature, diluted with hexanes, filtered and concentrated. The crude oil was purified by flash chromatography (100% hexanes) to yield 3OA (750 mg, 76%) as a clear oil. 1H NMR (400 MHz, CDCl3) delta ppm 2.31 (s, 3 H) 5.31 (dd, /=10.99, 1.10Hz, 1 H) 5.62 (dd, J=17.59, 1.10 Hz, 1 H) 6.84 (dd, J=17.04, 10.99 Hz, 1 H) 7.26 – 7.35 (m, 3 H).

The chemical industry reduces the impact on the environment during synthesis 116632-39-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/76431; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, I believe this compound will play a more active role in future production and life. 61203-48-3

Examples 13.b.-16.b.[207] The intermediate 4-amino-6,7-methylenedioxyquinoline o-iodobenzamide derivatives used in Examples 13.a.-16.a. were prepared using the following general procedure. [208] A 2.0M solution of oxalyl chloride in CH2Cl2 (1.3 equiv.) was added to a solution of 2-iodo-5,6-dimethoxybenzoic acid (1.0 equiv.) in anhydrous CH2Cl2 (¡ì 60 mL per 10 mmol benzoic acid) and the solution stirred at reflux for 3 h. The mixture was allowed to cool and was then concentrated to dryness in vacuo. To the residue was added a solution of appropriate 4-amino-6,7-dimethoxyquinoline (1.0 equiv), triethylamine (2 equiv.) in CH2Cl2 (¡ì 60 mL per 4 mmol aminoquinoline). The reaction mixture was then stirred at reflux under N2. . In the case of those derivatives that have an alkylamine incorporated in their structure, the residue was partitioned between CHCl3 and 10% NaOH. The aqueous layer was repeatedly separated with CHCl3. All of the CHCl3 solutions (initial partition and extracts) were combined and dried (MgSO4). The aqueous layer was neutralized with 20% NaOH and extracted with CHCl3, dried (MgSO4) and evaporated. [209] Example 13.b. N-(6,7-Methylenedioxyquinolin-4-yl)-N-[(2-(t- butyldimethylsilanyloxy)-ethyl]-2-iodo-4,5-dimethoxybenzamide. Prepared from 4-[N-[2-(t-Butyldimethylsilanyloxy)]ethyl]amino-6,7-methylenedioxyquinoline (400 mg, 1.15 mmol) in 51.7% yield with a reaction time of 12 h, from the acid chloride prepared using 5.0 mmol of oxalyl chloride and 1.38 mmol of 2-iodo-5,6- dimethoxybenzoic acid. Compound 8h had: mp 79-80 qC; IR (KBr); 1653 1H NMR (CDCl3); 0.004 (d, 3H, J = 4.2Hz), 0.82 (s, 9H), 3.26 (s, 3H), 3.67 (s, 3H), 3.84- 4.02 (m, 4H), 6.13 (d, 2H, J = 4Hz), 6.40 (s, 1H), 7.02 (s, 1H), 7.33 (d, 1H, J = 4.2Hz), 7.36 (s, 1H), 7.42 (s, 1H), 8.52 (d, 1H, J = 4Hz); HRMS calcd for C27H33ISiN2O6H 637.1232; observed 637.1212

The chemical industry reduces the impact on the environment during synthesis 61203-48-3. 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.; WO2012/15875; (2012); 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 148870-57-9 as follows. 148870-57-9

Example 1:Preparation of 7,8-dimethoxy-3- [3- [[(1 S)-(4,5-dimethoxybenzocyclobutan-1- yl)methyl] methylamino] propyll-1 ,3-de-hydro-7,8-dimethoxy-2H-3-benzazepin-2-one oxalate (De-hydro ivabradine oxalate salt) 3-[3-lodopropylj-7,8-dimethoxy- I H-3-benzazepin-2(3H)-one (100 gm),dimethylformamide (800 ml), potassium carbonate (140 gm) and (S)-N-[(4,5-dimethoxybenzocyclobut- 1 -yl)-methyl]-N-(methyl)amine hydrochloride (40 gm) were added and then heated to 40 to 45C. The reaction mass was maintained for 17 hours at 40 to 45C and then cooled to room temperature. To the reaction mass were added hydrochloric acid (iN, 3000 ml) and ethyl acetate (2000 ml). The layers were separatedand the aqueous layer was extracted with ethyl acetate. Combined organic layers were dried with sodium sulfate and then concentrated to obtain a residual solid. To the residual solid was added ethyl acetate (750 ml) and then added a solution of oxalic acid (27 gm) in acetone (100 ml). The reaction mass was stirred for 2 hours at room temperature and filtered. The solid obtained was dried to obtain 90 gm of de-hydro ivabradine oxalate salt.Chromatographic purity of de-hydro ivabradine oxalate salt: 96.5%.

According to the analysis of related databases, 148870-57-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; MURALIDHARA REDDY, Dasari; SRINIVASA RAO, Thungathurthy; VAMSI KRISHNA, Bandi; WO2013/150544; (2013); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 660-49-1, name is 3-Fluoro-5-iodoaniline, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 660-49-1

3-Iodo-5-fluoro-1-nitrobenzene (5.2 g; 19.48 mmol) is dissolved in a 4/3 water/tetrahydrofuran mixture. Powdered iron (8.7 g; 156 mmol), followed by acetic acid (4.5 ml) are added at room temperature and the suspension formed is stirred overnight at 40 C. The reaction mixture is filtered over diatomaceous earth and poured on to water. The mixture is extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexane/ethyl acetate (3/1). The pure fractions are combined and the solvent is evaporated off. The residue is diluted with methylene chloride (30 ml), and pyridine (4,0 ml; 49.5 mmol) and trifluoroacetic anhydride (3.44 ml; 24.7 mmol) are added and the mixture is stirred for one hour at room temperature. The reaction solution is poured on to aqueous hydrochloric acid (1 M; 50 ml) and the mixture is extracted twice with ethyl acetate (50 ml). The combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexanelethyl acetate (9/1). The pure fractions are combined and the solvent is evaporated off. [00367] Yield: 5.40 g (98%) as a white solid. [00368] MS: 333 (M)

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, 660-49-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Basilea Pharmaceutica AG; US6821980; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19094-56-5, Adding a certain compound to certain chemical reactions, such as: 19094-56-5, name is 2-Chloro-5-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 19094-56-5.

1. Synthetic routeWherein, the condition (b) is (COCl)2, CH2Cl2, DMF/Pyr, CH3OH, 2 to 3 h, r.t.2, the synthesis step(1) The compound B (B1,B2,B3) of the compound of Example 1 after purification (1 g, 3.16 mmol, 3.16 mmol, 3.54 mmol) was weighed under nitrogen, after adding 20 mL of ultra-dry anhydrous dichloromethane (DCM) and stirring to dissolve completely, add three times the amount of oxalyl chloride (9.48 mmol, 9.48 mmol, 10.62 mmol) and stir for 20-30 min; (2) Under nitrogen protection, 0.1 mL of anhydrous grade N,N-dimethylformamide (DMF) was added. After reacting for 1 h at room temperature, The reaction activated product is vacuum dried, And minimize external air entering the reaction device during operation; Use nitrogen as a shielding gas and add ultra-dry dichloromethane solvent. After stirring and dissolved at room temperature, Add twice the amount of anhydrous pyridine (6.32 mmol, 6.32 mmol, 7.08 mmol), The reaction was stirred for 30 min; finally, twice the amount of ultra-dry methanol (6.32 mmol, 6.32 mmol, 7.08 mmol) was added under a nitrogen atmosphere at room temperature. The reaction was stirred for 3 h or more; the reaction end point was detected by TLC [developing agent: V (petroleum ether)/V (ethyl acetate) = 20/1];(3) After the reaction is completed, it is extracted by washing with ethyl acetate. And dried over anhydrous MgSO4, filtered and concentrated. The crude product of the intermediate C(C1,C2,C3) was obtained, purified by silica gel column chromatography [eluent: V ( petroleum ether) / V (ethyl acetate) = 50/1] obtaining the compound intermediate C (C1,C2,C3), colorless oily liquid with yields of 72%, 58% and 63%, respectively.

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, 2-Chloro-5-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong University of Technology; Zhao Suqing; Zhang Bingjie; Feng Dongyan; Zhong Yingying; Huang Jinqu; Wu Ke; Ling Huaying; Tan Qiting; Chen Yanting; Zhao Jiawei; Ma Zhuolin; Jiang Zhengyun; Yang Yang; Zhu Qiuyan; Hong Weiqian; (37 pag.)CN110143869; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 624-75-9 name is 2-Iodoacetonitrile, 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. 624-75-9

benzoic acid (0.25 mmol, 30.6 mg), PhCH2CH2CH(Bpin) 2 (0.375 mmol, 139.8 mg) was added to a sealed tube.The reaction tube was replaced with a nitrogen atmosphere, and then 2 mL of tetrahydrofuran was added.The reaction tube was placed at -30 C under a nitrogen atmosphere.Add methyl lithium (0.625mmol, 1.6mol/L in Et2O), stir for 5min, then reverseIt should be placed in a pot at 100 C for 8 h. Subsequently, p-methoxybenzyl chloride (0.5 mmol, 78.3 mg) was added to the reaction tube under a nitrogen atmosphere, and the reaction was continued at 100 C for 6 h. At the end of the reaction, water and ethyl acetate were added for extraction, and the product was obtained by column chromatography to give a yield of 90%.

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

Reference:
Patent; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute Suzhou Institute; Liu Chao; Sun Wei; Wang Lu; (61 pag.)CN108373398; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-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. 660-49-1

Dissolve 3-fluoro-5-iodoaniline (600mg, 2. 53MMOL) (prepared as described in published PCT International Application W096/23783 A1, published August 8,1996), METHANESULFONYL chloride (896mg, 7. 83MMOL), triethylamine (1. 91G, 18.9mmol), and N, N-dimethylamino-4-pyridine (31MG, 0. 253MMOL) in CH2CK (lOmL) and stir at room temperature overnight. Dilute with L. OON aqueous HC1 (20ML) and extract into ethyl acetate. Dry (MGS04) and concentrate organics to a yellow solid. Dissolve solid in THF (50ML) and add L. OM tetrabutylammonium fluoride (2.8mL). Heat to reflux for 3. 5h. Cool to room temperature, dilute with H20, and extract into ethyl acetate. Dry (MGS04) and concentrate organics. Chromatograph on silica gel (40g), eluting with 20% to 35% ethyl acetate/hexanes affords 618MG (78%) of the title compound as a white solid. MS (ES) 314 (M-H) ; HPLC shows 100% purity.

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 660-49-1.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/52847; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-76-0, name is 2-Iodoethanol, 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. 624-76-0

Preparation of tert-butyl(2-iodoethoxy)dimethylsilane After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30 C. to 40 C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL). The organic layer was washed again with salt water (30 mL*3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90%) of a target compound. This compound was used as it was for the next reaction without purification.

Statistics shows that 624-76-0 is playing an increasingly important role. we look forward to future research findings about 2-Iodoethanol.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; US2014/249162; (2014); A1;,
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. 82998-57-0, name is 3-Iodo-4-methylbenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 82998-57-0

i) Production of 3-iodo-N,4-dimethylbenzamide 3-Iodo-4-methylbenzoic acid (9.84 g) was dissolved in THF (50 ml) and thionyl chloride (4 ml) and DMF (0.05 ml) were added. The mixture was heated under reflux for 3 hrs. The reaction mixture was concentrated under reduced pressure to give 3-iodo-4-methylbenzoyl chloride (10.18 g) as a brown powder.

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; Kusaka, Masami; EP1348706; (2003); 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. 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, A new synthetic method of this compound is introduced below., 82998-57-0

Step 1: To a solution of 3-iodo-4-methyl-benzoic acid (10.0 g, 38.2 mmol) in methanol (70 ml) is added concentrated sulfuric acid (0.5 ml). The reaction mixture is heated at 70C for 48 hours, cooled to room ambient temperature and then concentrated. After that, ethyl acetate (100 ml) and aqueous NaHCO3 (saturated, 100 ml) solution are added to the residue. The organic layer is separated and washed again with aqueous NaHCO3 (saturated, 100 ml) solution. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to yield 3-iodo-4-methyl-benzoic acid methyl ester 1. It is used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1 H), 7.87 (d, 1 H, J = 8.4 Hz), 7.48 (d, 1 H, J = 8.4 Hz), 3.85 (s, 3 H), 3.35 (s, 3H); LC-MS m/z: 277.0 (M+1).

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; Novartis AG; DIERKS, Christine; WARMUTH, Markus; WU, Xu; (20 pag.)EP2162190; (2016); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com