Tag: M.W=300-400

Application of 628-77-3, 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. 628-77-3 name is 1,5-Diiodopentane, 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.

Diiodopentane (0.63 mL, 4.21 mmol, 5 eq) and potassium carbonate (116 mg, 0.84 mmol, Ieq) were added to a solution of phenol 64 (400 mg, 0.84 mmol) in acetone (4 mL, dried overmolecular sieves). The reaction mixture was then warmed to 60C and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 15in 90% yield. LC/MS, 3.90 mm (ES+) m/z (relative intensity)670.91 ([M], 100). 1H NMR (400MHz, CDCI3) 5 7.23 (s, I H), 6.69 (s, I H), 6.60 (s, I H), 5.87 (d, J = 8.8 Hz, I H), 5.83 – 5.68(m, J = 5.6 Hz, I H), 5.15 – 5.01 (m, 2H), 4.67 -4.58 (m, I H), 4.45 – 4.35 (m, I H), 4.04 – 3.93(m, 2H), 3.91 (s, 3H), 3.73 (td, J= 10.0, 3.8 Hz, IH), 3.25-3.14 (m, J= 8.5, 7.0 Hz,2H), 2.92 (dd, J= 16.8, 10.3 Hz, IH), 2.38 (d, J= 16.8 Hz, IH), 1.95-1.81 (m, 4H), 1.77 (s,3H), 1.64-1.49 (m, 2H), 0.88 (s, 9H), 0.25 (s, 3H), 0.23 (s, 3H).

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; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius, Hendrikus, Cornelis; WO2015/52535; (2015); A1;; ; Patent; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius Hendrikus Cornelis; WO2015/52534; (2015); A1;,
Iodide – Wikipedia,
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Application of 628-77-3,Some common heterocyclic compound, 628-77-3, name is 1,5-Diiodopentane, molecular formula is C5H10I2, 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 141:(S)-1 -(1 -(4-bromophenyl)ethyl)piperidineTo a solution of (S)-i -(4-bromophenyl)ethanamine (1 .439 mL, 10.00 mmol) in DMF, were added potassium carbonate (4.14 g, 30.0 mmol) and 1,5-di- iodopentane (2.98 mL, 19.99 mmol). The reaction mixture was heated at 90 C in DMF for 16 h. The reaction mixture was concentrated, the product was extractedwith ethyl acetate and purification was done using column chromatography (silica gel, 30 % CHCI3 in DCM) to yield the title compound.Yield: 2 g (74.6%); 1H NMR (DMSO-d6, 300 MHz): 6 7.4 – 7.6 (d, 2H), 7.1 – 7.3 (d, 2H), 3.2 – 3.3 (m, 1 H), 2.1 – 2.4 (m, 4H), 1.4 – 1.5 (m, 4H), 1.3 – 1.4 (m,2H), 1.1 – 1.2 (m, 3H); MS (ESl+): m/z 269 [M+H] HPLC Purity: 96.30 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Diiodopentane, its application will become more common.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GUPTE, Amol; KANDRE, Shivaji; GADEKAR, Pradip, Keshavrao; CHAVAN, Sambhaji; JADHAV, Ravindra, Dnyandev; THAKRE, Gajanan, Amrutrao; BAJAJ, Komal; JANRAO, Ravindra, Ashok; DEHADE, Amol; GAIKWAD, Nitin; KADAM, Kishorkumar; MORE, Tulsidas, Sitaram; GUHA, Tandra; SEELABOYINA, Balapadmasree; SABLE, Vikas, Vasant; WO2015/110999; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 811842-30-5, name is 2-Bromo-1-fluoro-4-iodobenzene, 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 811842-30-5

To a solution of 2-bromo-1-fluoro-4-iodobenzene 16-a (3.3 g, 11.0 mmol) in toluene (5.5 ml) was added (2-methylpyrimidin-5-yl)methanol 4-a (1.5 g, 12.1 mmol), 1,10- phenanthroline (396 mg, 2.2 mmol), copper (I) iodide (209 mg, 1.1 mmol), and cesium carbonate (5.0 g, 15.4 mmol). The reaction was stirred at 110C for 2 days, and then cooled to room temperature, diluted with ethyl acetate, and filtered over celite. A saturated aqueous solution of ammonium chloride was added to the filtrate, the organic layer was separated, and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography provided Intermediate 16-b as a yellow solid.

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

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2015/77866; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature 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-iodoben- zene, 101 g (664 mmol) of 2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetraborate are dissolved in 1000 ml of THF and 600 ml of water, and degassed. 9.3 g (13.3 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1 g (20 mmol) of hydrazinium hydroxide are added. The reaction mixture is then stirred under a protective gas atmosphere at 70 C. for 48 h. The cooled solution is supplemented with toluene, washed repeatedly with water, dried and concentrated. The product is purified via colunm chromatography on silica gel with toluene/heptane (1:2). Yield: 155 g (553 mmol), 83% of theory.

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; EBERLE, Thomas; JATSCH, Anja; GROSSMANN, Tobias; KROEBER, Jonas Valentin; MONTENEGRO, Elvira; JOOSTEN, Dominik; WERN, Caroline; (238 pag.)US2019/119260; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic 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 61203-48-3, category: iodides-buliding-blocks

General procedure: To a stirred solution of 2-iodobenzoic acids a (10 mmol) in CH2Cl2, was added DCC (dicyclohexylcarbodiimide, 11 mmol), DMAP (Dimethylaminopyridine, 2 mmol) and alcohols b (10 mmol) in sequence. The resulting solution was stirred overnight at room temperature then filtered through a sand core funnel and washed with diethyl ether (2 x 40mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash column chromatography to obtain the pure product c in moderate to good yields. To a soluton of 2-iodobenzoates c in Et3N (5 mL) was added PdCl2 (PPh3)2 (4 mol %) and CuI (2 mol %) and the reaction vial was flushed with Ar and the reaction mixture was stirred for 5 minutes. A solution of propargyl alcohols d (1.05 equiv) in Et3N (5 mL) were then added dropwise through a syringe for 5 minutes. The resulting solution was stirred at room temperature overnight. When the reaction was considered complete as determined by TLC analysis, the mixture was quenched by addition of saturated aqueous ammonium chloride (10 mL) and extracted with ethyl ether (3 x 40 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash column chromatography to give 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, 2-Iodo-4,5-dimethoxybenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhu, Hai-Tao; Tong, Xiao-Juan; Zhou, Ni-Ni; Yang, De-Suo; Fan, Ming-Jin; Tetrahedron Letters; vol. 57; 49; (2016); p. 5497 – 5500;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 400-97-5,Some common heterocyclic compound, 400-97-5, name is 1-Iodo-2-nitro-4-(trifluoromethyl)benzene, molecular formula is C7H3F3INO2, 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.

2) A solution having 30 g of 4-iodo-3-nitrobenzotrifluoride obtained in the preceding step dissolved in 300 ml of acetic acid, was heated, and 26.43 g of reduced iron was added thereto over a period of 15 minutes at a temperature of from 85 to 95 C. Then, the mixture was reacted for further 5 minutes at the same temperature. After completion of the reaction, the reaction mixture was cooled with ice, and insoluble matters were filtered off using celite. The filtration cake was thoroughly washed with ethyl acetate, and the washing liquid and the filtrate were mixed, followed by washing with water for 5 times. The obtained ethyl acetate layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 25.52 g of oily 3-amino-4-iodobenzotrifluoride. The NMR spectrum data of this product are as follows. hu 1H-NMR deltappm [Solvent: CDCl3 ] 6.70 (dd,1H), 6.93 (d,1H), 7.73 (d,1H)

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-2-nitro-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US5998334; (1999); A;,
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: 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, SDS of cas: 112671-42-8

Under the protection of argon, dibenzothiophene-4-boronic acid (29.2 g, 128.1 mmol), 4-bromo-1-iodo-2-nitrobenzene (35.0 g, 106.8 mmol), Na2CO3 were sequentially added to the reaction flask. (34.0 g, 320.4 mmol), tetrakistriphenylphosphine palladium (6.17 g, 5.3 mmol), toluene (640 ml) and ethanol (160 ml), and the reaction mixture was stirred at 90 C for 3 hours. After the stirring was completed, poured into distilled water (160 ml), cooled to room temperature, and the organic phase was extracted with ethyl acetate.The organic phase is concentrated and combined by column chromatographyC5 (33.6 g, 82%).

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; Changchun Hai Purunsi Technology Co., Ltd.; Zhou Wenting; Cai Hui; (39 pag.)CN108822020; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), /V-(3-dimethylaminopropyl)-A^- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazoe (135 mg, 1.0 mmol), 7V,/V-diisopropylethylamine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na?.S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM ::: 0 : 100 to 30 : 70) to give JV-benzyl- 5-bromo-2-iodobenzamide (361 mg, 87 %) as a white solid.

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

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164948; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 28547-29-7, name is 2-Bromo-4-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 28547-29-7, Product Details of 28547-29-7

To a stirred solution of 4-iodo-2-bromobenzoic acid (5 g, 15.29 mmol) in ethyl alcohol (EtOH; 100 mL) was added sulfuric acid (H2SO4; 5 mL), and the reaction mixture was heated at 80 C. for 18 h. The reaction mixture was cooled to 25 C. and concentrated under reduced pressure. The residue was diluted with EtOAc (2*100 mL) and washed with H2O (100 mL). The combined EtOAc extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the compound as a pale yellow solid (5 g, 92%): 1H NMR (400 MHz, DMSO-d6) delta 8.04 (d, J=1.2 Hz, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 4.41 (q, J=7.2 Hz, 2H), 1.41 (t, J=7.2 Hz, 3H).

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; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com